37,298 results for "Florida Keys waterfront"
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Islamorada, Florida
Custom-Built Oceanfront Caribbean Home w/ Gorgeous Ocean & Sunrise Views
Located in Islamorada, Florida, United States. Custom-Built Oceanfront Caribbean Home w/ Gorgeous Ocean & Sunrise Views Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Caribbean home is on the ocean’s edge with 180 degrees of unobstructed ocean views and sunrises. With complete privacy, this site is home to famous movie shoots, celebrity weddings and family reunions.About The Caribbean ResortOur Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical fl
Islamorada, Florida
Luxurious Caribbean 2 Bedroom 2 Bath Home
Located in Islamorada, Florida, United States. Luxurious Caribbean 2 Bedroom 2 Bath Home Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.2 Bedrooms, 2 baths. Caribbean homes with 450-foot fishing pier and beach entry pool keep guest coming back. Its the off-shore fishing and diving that makes it so hard to leave. Located on a deep-water channel with protected dockage. 1 King Bed, 2 Full Beds, 1 Pull Out
Islamorada, Florida
Caribbean-Style Family Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
Located in Islamorada, Florida, United States. Caribbean-Style Family Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.About The Caribbean ResortOur Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees th
Islamorada, Florida
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
Located in Islamorada, Florida, United States. Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina King, Queen, 2 twins, 1 pullout. Custom designed and built from the ground up by resort owner Phil Sena with nothing compromised this luxurious Caribbean home is on the oceansedge with 180 degrees of unobstructed ocean views and sunrises. Withcomplete privacy, this site is home to famous movie shoots, celebrityweddings and family reunions.Caribbean homes with 450-foot fishing pier and beach entry pool keep guestcoming back. Its the off-shore fishing and diving that makes it so hard toleave. Located on a deep-water channel with protected dockage
Islamorada, Florida
BRAND NEW Island-design home located in Islamorada fishing capital of the world!
Located in Islamorada, Florida, United States. BRAND NEW Island-design home located in Islamorada fishing capital of the world! The Pink Sands House is located in the beautiful Lower Matecumbe island in close proximity to all your Class-A shopping, dining, and fishing needs. The Island-Design House is located in a quiet, private community with your own private gated sandy beach area with sunset views and crystal clear warm waters. For area info call or text Alexis at (305) 345-7217. Also, per month COMPLIMENTARY HOUSE CLEANING will be occur for rentals 2 or more months. Please note prices are subject to change based on season, holidays, occupancy, and weekly rates.
Islamorada, Florida
Experience Life in Islamorada: 1BR Condo
Located in Islamorada, Florida, United States. Experience Life in Islamorada: 1BR Condo Immerse yourself in our spacious 1-bedroom, 2-bathroom suite, offering a delightful haven for guests. Relax in the bedroom with two queen beds, an ensuite bathroom, and a private balcony. The living area features a snug queen sofa bed, a functional kitchen with a dining table for four, a second bathroom, and an additional balcony. While our property boasts an oceanfront location, not all units guarantee direct ocean views.At Caloosa Cove Resort, enjoy breathtaking vistas, a heated swimming pool, a serene beachfront, a convenient General Store, boat slips, and invigorating boat charters. With plenty of activities nearby, it's the perfect destination to unwind and fully immerse yourself in the captivating ambiance of Islamorada. Room assignments are based on availability at check-in, and specific views or locations cannot be guaranteed. Thank you for your understanding.
Islamorada, Florida
Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats
Located in Islamorada, Florida, United States. Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive into water sports. Enjoy nearby attractions like Anne's Beach, Theater of the Sea, and the History of Diving Museum.Experience a slice of paradise in this authentic room at our boutique beachfront resort! We offer a private lounge on the beach where you can relish the authentic island life experience. Enjoy a bike tour through the island, an outdoor pool, and a sun terrace with breathtaking views of Alligator Reef Lighthouse. Embark on boating excursions and dine at our delightful American restaurant. Relax, rejuvenate, and explore the serene beauty that awaits.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of $100/night/unit on the credit/debit
Islamorada, Florida
Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool
Located in Islamorada, Florida, United States. Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.The Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home.About The Caribbean ResortOur Caribbean ho
Islamorada, Florida
Water Front 3/3 Family and Boat Friendly Home, Great Views
Located in Islamorada, Florida, United States. Water Front 3/3 Family and Boat Friendly Home, Great Views This beautiful well-kept and spacious two story bay-side waterfront home is a perfect rental home for you and your family. The home has three bedrooms and three baths, 2/2 upstairs and 1/1 down. The expansive great room (22 ft. X 38ft.), which includes the kitchen, dining, sitting and living rooms with 60 inch hd tv overlooks the wide open views of hurricane creek, making entertaining or just chilling something to remember. The front of home has a balcony with chairs overlooking the park and partial view of the bay. . From the 96 ft. Dock you have a view of the bay and are able to fish, swim and tie up at least two boats. It is located at mile marker 73.5, on lower matecumbe key, making it close to islamorada restaurants and shopping. Within one mile of the home, you will find a convenient store, gas station, restaurant, lounge, hard ware store, bait and tackle store and ann’s beach. By boat, channel 2 and 5 are less than t
Islamorada, Florida
Tropical Paradise
Located in Islamorada, Florida, United States. Tropical Paradise Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat included. Bicycles available. Close to many restaurants, bars and places of interest.
Islamorada, Florida
Exceptional condo with panoramic views of the Atlantic Ocean.
Located in Islamorada, Florida, United States. Exceptional condo with panoramic views of the Atlantic Ocean. PROPERTY NAME: The Palms #30979901 Overseas Highway, Islamorada, FLLOCATION: Bayside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen with Corian counters, updated cabinetry and a little breakfast nook. All kitchen appliances are newer and the kitchen is complete with pots, pans, dishes, glasses and flatware. The two bathrooms have been updated - one features a tub and shower combination and the other a walk-in shower. The master suite has small office area with a desk, monitor and keyboard. Bring your computer there's even a printer. There is a queen size bed, walk-in closet, and a dressing area.
Islamorada, Florida
Leisure Inn Islamorada - 3/2 canal home on a double lot, bring all of the toys!
Located in Islamorada, Florida, United States. Leisure Inn Islamorada - 3/2 canal home on a double lot, bring all of the toys! This charming Florida home is situated on a double lot with a full sea basin on an ocean side, deep water canal...seconds from the Atlantic Ocean and a straight shot to Alligator Reef. This one story home has 3 bedrooms, 2 baths, a spacious kitchen and living area. Sleeps 6 guests comfortably, 8 guests if using the living room sleeper sofa. Access to an exclusive, nearby club is included in your stay. The club offers free access to the pool, boat ramp, and fuel at cost for guests.
Islamorada, Florida
Waves of Luxury: Access to Bayside Pool and Boat Slips. FREE Parking Onsite!
Located in Islamorada, Florida, United States. Waves of Luxury: Access to Bayside Pool and Boat Slips. FREE Parking Onsite! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typic
Islamorada, Florida
Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
Located in Islamorada, Florida, United States. Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking! Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of the guest rooms and suites in our three-bedroom house is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual elegance of the tropics with our resort amenities. Guests have access to all the amenities they might possibly need right on the premises, including a restaurant, bar, swimming pool, and slips for those visiting with boats. But if you want to venture offsite, we have a shuttle service that can take you around.PLEASE NOTE:- The property requires a damage deposit of USD 100/night/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability u
Islamorada, Florida
Have Fun at this Beachfront Paradise with Outdoor Pools, Free Parking!
Located in Islamorada, Florida, United States. Have Fun at this Beachfront Paradise with Outdoor Pools, Free Parking! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential
Islamorada, Florida
Sun, Sand, and Splendor: 2 Relaxing Units. Water Activities and Pool Onsite!
Located in Islamorada, Florida, United States. Sun, Sand, and Splendor: 2 Relaxing Units. Water Activities and Pool Onsite! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typic
Islamorada, Florida
Waterfront with a pool & private beach access.
Located in Islamorada, Florida, United States. Waterfront with a pool & private beach access. Waterfront with pool. Private beach access within a mile. All amenities needed to enjoy a fun and relaxing vacation. A fully furnished three-bedroom, two-bathroom house located in Islamorada with water access. The property has dock space for a boat up to 35' (bow to stern). And a cleaning table.The Master bedroom is located on the second floor and has a king-size bed and its private bathroom. The second and third bedrooms are also on the second floor. 1 bedroom has a queen bed and is connected to the bathroom and the third bedroom has a full size bed and access to the2nd bathroom. There is a living room, dining room, second full bath, and a fully equipped kitchen, as well as a large wrap-around balcony that overlooks the canal.A full-size washer and dryer are located inside the premises. A circular driveway and ample parking for vehicles. The barbecue grill is under the stairs.WiFi internet, televisions in all bedrooms and living room.
Islamorada, Florida
Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking!
Located in Islamorada, Florida, United States. Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical res
Islamorada, Florida
Tropical Haven in the Heart of Islamorada
Located in Islamorada, Florida, United States. Tropical Haven in the Heart of Islamorada Immerse yourself in the luxury and beauty of Oceanside Resort, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends. Every stylishly furnished bedroom comes complete with its own en suite bathroom, and an expansive living/dining area opens directly onto a private patio & pool. Plus, savor delicious food prepared fresh from your own fully equipped kitchen or take advantage of numerous nearby restaurants, such as Morada Bay and Square Grouper, where breath taking views meet tantalizing cuisine. Our home, at mile marker 82, is just minutes away!Private dockage is available upon reservation and for a nominal fee. Dockage is located just steps away on the bay side and will accommodate a boat up to 35 feet in length. Please note, this rental allows a minimum
Islamorada, Florida
Ultimate Vacation in Islamorada! Short Drive to Marathon International Airport
Located in Islamorada, Florida, United States. Ultimate Vacation in Islamorada! Short Drive to Marathon International Airport Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typ
Islamorada, Florida
Charming Islamorada house with waterfront, private dock and beach
Located in Islamorada, Florida, United States. Charming Islamorada house with waterfront, private dock and beach Nestled in Islamorada, this delightful house offers a peaceful and serene retreat for guests. With 2 bedrooms, including a king bed, queen bed, and full bed, there's plenty of space for everyone to relax and recharge. The bathrooms are equipped with a bathtub, shower, and hair dryer for added convenience. Whether you're lounging in the cozy living area or enjoying the brilliant sunshine on the outdoor patio, you'll feel right at home. Plus, amenities like WiFi, a washing machine, and AC ensure a comfortable stay. It's easy to see why you'll be able to unwind at our place. The property has access to a private beach considered one of the best in the area. The beach is within a five minute walk or you can use one of the four bikes available. There are four kayaks that can be used to enjoy the area.
Islamorada, Florida
Enjoy a Hassle-free Stay! Unit w/ Full Kitchen, Beachfront, Outdoor Pool
Located in Islamorada, Florida, United States. Enjoy a Hassle-free Stay! Unit w/ Full Kitchen, Beachfront, Outdoor Pool Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residentia
Islamorada, Florida
Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Parking!
Located in Islamorada, Florida, United States. Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Parking! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typica
Islamorada, Florida
Coastal Island Retreat with Private Beach Access!
Located in Islamorada, Florida, United States. Coastal Island Retreat with Private Beach Access! Welcome to Time Well Wasted, an ideal retreat located in the highly sought-after neighborhood of Port Antiqua on Lower Matecumbe Key. This recently-renovated vacation rental is a haven of comfort.A highlight of every stay is exclusive access to the private bay-front homeowners' beach, offering an inviting sandy escape for relaxation and recreation.One of the most notable features of this home is the abundance of natural light that streams through the skylights, creating a warm and inviting atmosphere throughout the entire home. With three bedrooms, this residence is perfectly suited for families or groups of friends. The home features an expansive porch adjacent to the kitchen and living room that is furnished with cozy patio furniture, creating a perfect spot to enjoy the outdoors.The master bedroom boasts a king-sized bed and a private ensuite bathroom. The two guest bedrooms are thoughtfully designed for comfort and convenience. One
Islamorada, Florida
Custom-Built Oceanfront Caribbean Home w/ Gorgeous Ocean & Sunrise Views
Located in Islamorada, Florida, United States. Custom-Built Oceanfront Caribbean Home w/ Gorgeous Ocean & Sunrise Views Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Caribbean home is on the ocean’s edge with 180 degrees of unobstructed ocean views and sunrises. With complete privacy, this site is home to famous movie shoots, celebrity weddings and family reunions.About The Caribbean ResortOur Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical fl
$1,073
/ night
Islamorada, Florida
Luxurious Caribbean 2 Bedroom 2 Bath Home
Located in Islamorada, Florida, United States. Luxurious Caribbean 2 Bedroom 2 Bath Home Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.2 Bedrooms, 2 baths. Caribbean homes with 450-foot fishing pier and beach entry pool keep guest coming back. Its the off-shore fishing and diving that makes it so hard to leave. Located on a deep-water channel with protected dockage. 1 King Bed, 2 Full Beds, 1 Pull Out
$424
/ night
Islamorada, Florida
Caribbean-Style Family Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
Located in Islamorada, Florida, United States. Caribbean-Style Family Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.About The Caribbean ResortOur Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees th
$425
/ night
Islamorada, Florida
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
Located in Islamorada, Florida, United States. Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina King, Queen, 2 twins, 1 pullout. Custom designed and built from the ground up by resort owner Phil Sena with nothing compromised this luxurious Caribbean home is on the oceansedge with 180 degrees of unobstructed ocean views and sunrises. Withcomplete privacy, this site is home to famous movie shoots, celebrityweddings and family reunions.Caribbean homes with 450-foot fishing pier and beach entry pool keep guestcoming back. Its the off-shore fishing and diving that makes it so hard toleave. Located on a deep-water channel with protected dockage
$1,028
/ night
Islamorada, Florida
BRAND NEW Island-design home located in Islamorada fishing capital of the world!
Located in Islamorada, Florida, United States. BRAND NEW Island-design home located in Islamorada fishing capital of the world! The Pink Sands House is located in the beautiful Lower Matecumbe island in close proximity to all your Class-A shopping, dining, and fishing needs. The Island-Design House is located in a quiet, private community with your own private gated sandy beach area with sunset views and crystal clear warm waters. For area info call or text Alexis at (305) 345-7217. Also, per month COMPLIMENTARY HOUSE CLEANING will be occur for rentals 2 or more months. Please note prices are subject to change based on season, holidays, occupancy, and weekly rates.
$308
/ night
Islamorada, Florida
Experience Life in Islamorada: 1BR Condo
Located in Islamorada, Florida, United States. Experience Life in Islamorada: 1BR Condo Immerse yourself in our spacious 1-bedroom, 2-bathroom suite, offering a delightful haven for guests. Relax in the bedroom with two queen beds, an ensuite bathroom, and a private balcony. The living area features a snug queen sofa bed, a functional kitchen with a dining table for four, a second bathroom, and an additional balcony. While our property boasts an oceanfront location, not all units guarantee direct ocean views.At Caloosa Cove Resort, enjoy breathtaking vistas, a heated swimming pool, a serene beachfront, a convenient General Store, boat slips, and invigorating boat charters. With plenty of activities nearby, it's the perfect destination to unwind and fully immerse yourself in the captivating ambiance of Islamorada. Room assignments are based on availability at check-in, and specific views or locations cannot be guaranteed. Thank you for your understanding.
$228
/ night
Islamorada, Florida
Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats
Located in Islamorada, Florida, United States. Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive into water sports. Enjoy nearby attractions like Anne's Beach, Theater of the Sea, and the History of Diving Museum.Experience a slice of paradise in this authentic room at our boutique beachfront resort! We offer a private lounge on the beach where you can relish the authentic island life experience. Enjoy a bike tour through the island, an outdoor pool, and a sun terrace with breathtaking views of Alligator Reef Lighthouse. Embark on boating excursions and dine at our delightful American restaurant. Relax, rejuvenate, and explore the serene beauty that awaits.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of $100/night/unit on the credit/debit
$327
/ night
Islamorada, Florida
Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool
Located in Islamorada, Florida, United States. Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.The Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home.About The Caribbean ResortOur Caribbean ho
$310
/ night
Islamorada, Florida
Water Front 3/3 Family and Boat Friendly Home, Great Views
Located in Islamorada, Florida, United States. Water Front 3/3 Family and Boat Friendly Home, Great Views This beautiful well-kept and spacious two story bay-side waterfront home is a perfect rental home for you and your family. The home has three bedrooms and three baths, 2/2 upstairs and 1/1 down. The expansive great room (22 ft. X 38ft.), which includes the kitchen, dining, sitting and living rooms with 60 inch hd tv overlooks the wide open views of hurricane creek, making entertaining or just chilling something to remember. The front of home has a balcony with chairs overlooking the park and partial view of the bay. . From the 96 ft. Dock you have a view of the bay and are able to fish, swim and tie up at least two boats. It is located at mile marker 73.5, on lower matecumbe key, making it close to islamorada restaurants and shopping. Within one mile of the home, you will find a convenient store, gas station, restaurant, lounge, hard ware store, bait and tackle store and ann’s beach. By boat, channel 2 and 5 are less than t
$271
/ night
Islamorada, Florida
Tropical Paradise
Located in Islamorada, Florida, United States. Tropical Paradise Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat included. Bicycles available. Close to many restaurants, bars and places of interest.
$271
/ night
Islamorada, Florida
Exceptional condo with panoramic views of the Atlantic Ocean.
Located in Islamorada, Florida, United States. Exceptional condo with panoramic views of the Atlantic Ocean. PROPERTY NAME: The Palms #30979901 Overseas Highway, Islamorada, FLLOCATION: Bayside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen with Corian counters, updated cabinetry and a little breakfast nook. All kitchen appliances are newer and the kitchen is complete with pots, pans, dishes, glasses and flatware. The two bathrooms have been updated - one features a tub and shower combination and the other a walk-in shower. The master suite has small office area with a desk, monitor and keyboard. Bring your computer there's even a printer. There is a queen size bed, walk-in closet, and a dressing area.
$118
/ night
Islamorada, Florida
Leisure Inn Islamorada - 3/2 canal home on a double lot, bring all of the toys!
Located in Islamorada, Florida, United States. Leisure Inn Islamorada - 3/2 canal home on a double lot, bring all of the toys! This charming Florida home is situated on a double lot with a full sea basin on an ocean side, deep water canal...seconds from the Atlantic Ocean and a straight shot to Alligator Reef. This one story home has 3 bedrooms, 2 baths, a spacious kitchen and living area. Sleeps 6 guests comfortably, 8 guests if using the living room sleeper sofa. Access to an exclusive, nearby club is included in your stay. The club offers free access to the pool, boat ramp, and fuel at cost for guests.
$190
/ night
Islamorada, Florida
Waves of Luxury: Access to Bayside Pool and Boat Slips. FREE Parking Onsite!
Located in Islamorada, Florida, United States. Waves of Luxury: Access to Bayside Pool and Boat Slips. FREE Parking Onsite! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typic
$412
/ night
Islamorada, Florida
Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
Located in Islamorada, Florida, United States. Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking! Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of the guest rooms and suites in our three-bedroom house is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual elegance of the tropics with our resort amenities. Guests have access to all the amenities they might possibly need right on the premises, including a restaurant, bar, swimming pool, and slips for those visiting with boats. But if you want to venture offsite, we have a shuttle service that can take you around.PLEASE NOTE:- The property requires a damage deposit of USD 100/night/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability u
$446
/ night
Islamorada, Florida
Have Fun at this Beachfront Paradise with Outdoor Pools, Free Parking!
Located in Islamorada, Florida, United States. Have Fun at this Beachfront Paradise with Outdoor Pools, Free Parking! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential
$1,335
/ night
Islamorada, Florida
Sun, Sand, and Splendor: 2 Relaxing Units. Water Activities and Pool Onsite!
Located in Islamorada, Florida, United States. Sun, Sand, and Splendor: 2 Relaxing Units. Water Activities and Pool Onsite! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typic
$1,248
/ night
Islamorada, Florida
Waterfront with a pool & private beach access.
Located in Islamorada, Florida, United States. Waterfront with a pool & private beach access. Waterfront with pool. Private beach access within a mile. All amenities needed to enjoy a fun and relaxing vacation. A fully furnished three-bedroom, two-bathroom house located in Islamorada with water access. The property has dock space for a boat up to 35' (bow to stern). And a cleaning table.The Master bedroom is located on the second floor and has a king-size bed and its private bathroom. The second and third bedrooms are also on the second floor. 1 bedroom has a queen bed and is connected to the bathroom and the third bedroom has a full size bed and access to the2nd bathroom. There is a living room, dining room, second full bath, and a fully equipped kitchen, as well as a large wrap-around balcony that overlooks the canal.A full-size washer and dryer are located inside the premises. A circular driveway and ample parking for vehicles. The barbecue grill is under the stairs.WiFi internet, televisions in all bedrooms and living room.
$340
/ night
Islamorada, Florida
Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking!
Located in Islamorada, Florida, United States. Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical res
$394
/ night
Islamorada, Florida
Tropical Haven in the Heart of Islamorada
Located in Islamorada, Florida, United States. Tropical Haven in the Heart of Islamorada Immerse yourself in the luxury and beauty of Oceanside Resort, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends. Every stylishly furnished bedroom comes complete with its own en suite bathroom, and an expansive living/dining area opens directly onto a private patio & pool. Plus, savor delicious food prepared fresh from your own fully equipped kitchen or take advantage of numerous nearby restaurants, such as Morada Bay and Square Grouper, where breath taking views meet tantalizing cuisine. Our home, at mile marker 82, is just minutes away!Private dockage is available upon reservation and for a nominal fee. Dockage is located just steps away on the bay side and will accommodate a boat up to 35 feet in length. Please note, this rental allows a minimum
$692
/ night
Islamorada, Florida
Ultimate Vacation in Islamorada! Short Drive to Marathon International Airport
Located in Islamorada, Florida, United States. Ultimate Vacation in Islamorada! Short Drive to Marathon International Airport Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typ
$331
/ night
Islamorada, Florida
Charming Islamorada house with waterfront, private dock and beach
Located in Islamorada, Florida, United States. Charming Islamorada house with waterfront, private dock and beach Nestled in Islamorada, this delightful house offers a peaceful and serene retreat for guests. With 2 bedrooms, including a king bed, queen bed, and full bed, there's plenty of space for everyone to relax and recharge. The bathrooms are equipped with a bathtub, shower, and hair dryer for added convenience. Whether you're lounging in the cozy living area or enjoying the brilliant sunshine on the outdoor patio, you'll feel right at home. Plus, amenities like WiFi, a washing machine, and AC ensure a comfortable stay. It's easy to see why you'll be able to unwind at our place. The property has access to a private beach considered one of the best in the area. The beach is within a five minute walk or you can use one of the four bikes available. There are four kayaks that can be used to enjoy the area.
$206
/ night
Islamorada, Florida
Enjoy a Hassle-free Stay! Unit w/ Full Kitchen, Beachfront, Outdoor Pool
Located in Islamorada, Florida, United States. Enjoy a Hassle-free Stay! Unit w/ Full Kitchen, Beachfront, Outdoor Pool Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residentia
$1,031
/ night
Islamorada, Florida
Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Parking!
Located in Islamorada, Florida, United States. Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Parking! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typica
$454
/ night
Islamorada, Florida
Coastal Island Retreat with Private Beach Access!
Located in Islamorada, Florida, United States. Coastal Island Retreat with Private Beach Access! Welcome to Time Well Wasted, an ideal retreat located in the highly sought-after neighborhood of Port Antiqua on Lower Matecumbe Key. This recently-renovated vacation rental is a haven of comfort.A highlight of every stay is exclusive access to the private bay-front homeowners' beach, offering an inviting sandy escape for relaxation and recreation.One of the most notable features of this home is the abundance of natural light that streams through the skylights, creating a warm and inviting atmosphere throughout the entire home. With three bedrooms, this residence is perfectly suited for families or groups of friends. The home features an expansive porch adjacent to the kitchen and living room that is furnished with cozy patio furniture, creating a perfect spot to enjoy the outdoors.The master bedroom boasts a king-sized bed and a private ensuite bathroom. The two guest bedrooms are thoughtfully designed for comfort and convenience. One
$211
/ night
Custom-Built Oceanfront Caribbean Home w/ Gorgeous Ocean & Sunrise Views
Islamorada, Florida
$1,073/night
Luxurious Caribbean 2 Bedroom 2 Bath Home
Islamorada, Florida
$424/night
Caribbean-Style Family Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
Islamorada, Florida
$425/night
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
Islamorada, Florida
$1,028/night
BRAND NEW Island-design home located in Islamorada fishing capital of the world!
Islamorada, Florida
$308/night
Experience Life in Islamorada: 1BR Condo
Islamorada, Florida
$228/night
Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats
Islamorada, Florida
$327/night
Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool
Islamorada, Florida
$310/night
Water Front 3/3 Family and Boat Friendly Home, Great Views
Islamorada, Florida
$271/night
Tropical Paradise
Islamorada, Florida
$271/night
Exceptional condo with panoramic views of the Atlantic Ocean.
Islamorada, Florida
$118/night
Leisure Inn Islamorada - 3/2 canal home on a double lot, bring all of the toys!
Islamorada, Florida
$190/night
Waves of Luxury: Access to Bayside Pool and Boat Slips. FREE Parking Onsite!
Islamorada, Florida
$412/night
Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
Islamorada, Florida
$446/night
Have Fun at this Beachfront Paradise with Outdoor Pools, Free Parking!
Islamorada, Florida
$1,335/night
Sun, Sand, and Splendor: 2 Relaxing Units. Water Activities and Pool Onsite!
Islamorada, Florida
$1,248/night
Waterfront with a pool & private beach access.
Islamorada, Florida
$340/night
Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking!
Islamorada, Florida
$394/night
Tropical Haven in the Heart of Islamorada
Islamorada, Florida
$692/night
Ultimate Vacation in Islamorada! Short Drive to Marathon International Airport
Islamorada, Florida
$331/night
Charming Islamorada house with waterfront, private dock and beach
Islamorada, Florida
$206/night
Enjoy a Hassle-free Stay! Unit w/ Full Kitchen, Beachfront, Outdoor Pool
Islamorada, Florida
$1,031/night
Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Parking!
Islamorada, Florida
$454/night
Coastal Island Retreat with Private Beach Access!
Islamorada, Florida
$211/night