72,107 properties available

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

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.

Located in Islamorada, Florida, United States. Large bay-front home with dockage, pool and beach in the heart of Islamorada The Dock View House is one of three homes at Mermaid's Bay Boutique Estate. This private waterfront oasis sprawls 3.5 acres in the heart of Islamorada, just moments away from all of the top attractions and restaurants. The estate features over 300 feet of open-water views, a large boat basin and a resort-style pool and spa. This estate-style home was originally built in the 1940s and has been preserved and tastefully updated to maintain the Florida Keys charm. Large windows offer waterfront views out of almost every room. In the heart of the house is a double-sided fireplace (non-working), with a chef-style kitchen and dining room on one side, and a vaulted-ceiling living room and solarium on the other. To the left of the house are two ensuites, one downstairs with two queen size beds and one upstairs with a king bed. There is also a half-bath located in the stairwell hallway. The right side of the house mirro

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.

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

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

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

Located in Islamorada, Florida, United States. Updated Unit with Beautiful Florida Bay Sunsets PROPERTY NAME: The Palms #41779901 Overseas Highway, Islamorada, FLLOCATION: Oceanside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. This one bedroom unit has partial views of the ocean and a good view of the Florida Bay. It is perfectly proportioned - large living area and large bedroom and dressing area with separate linen closet and walk-in closet. The kitchen and baths have been updated. You'll be glad you chose this unit for your holiday in the Keys. Bedding is king. This property is professionally managed by Keys Holiday Rentals.Sleeping Arrangements: Sleeps 2-3 comfortably

Located in Islamorada, Florida, United States. Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean. PROPERTY NAME: Beacon Reef #30683201 Old Highway, Islamorada, FloridaLOCATION: Ocean Side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: Enjoy a relaxing stay here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other property "up north" you can relish all the delightful amenities of their condo. This unit is beautifully appointed and offers comfortable accommodations - fully equipped kitchen, full size washer and dryer, king size bed in the master and two full size beds for your guests. Located in the heart of Islamorada, you'll love the charm of an ocean front complex with the large freeform pool, hot tub, sandy beach and dock privileges. There's even a well-equipped gym for exercise enthusiasts. You'll find this location exceptionally convenient to fabulous dining and recreati

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.

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.

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.

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

Located in Islamorada, Florida, United States. Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life! Come enjoy the beautiful Florida Keys in this new build stylish villa located in Islamorada close to shopping & restaurants but private and secluded perfect for a short term retreat to live a real island life! Welcoming seasonal snowbirds as well as short term group trips. Entire home completely stocked with all linens/supplies for ease, comfort and finished with immaculate decor. 5 bedrooms, 3 full bathrooms, private outdoor shower and private outdoor bath tub, 2 family private setup with each floor boasting its own living room, kitchen, coffee bars, ocean front master on each as well as private entrances per floor. Upstairs kitchen decked w/ Italian Bertazzoni appliances, 4 seat island with bar sink & wine fridge. Each bedroom equipped with smart TV's, balconies with outdoor furniture to sip sunset cocktails or enjoy nespresso watching the phenomenal sunrise each morning. Each bedroom has a walk-in or ex

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

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

Located in Islamorada, Florida, United States. Stunning Oceanfront Villa, Luxe Resort Perks at the Islands of Islamorada Resort Welcome to The Islands of Islamorada Resort: Your Luxury Oceanfront Retreat Awaits!Indulge in the epitome of coastal elegance at The Islands of Islamorada. Set in the stunning Florida Keys, our opulent three-story waterfront villas offer a premier escape for those seeking both serene relaxation and thrilling adventure.Accommodations:Discover unrivaled comfort and sophistication in our exquisite villas:- Four Sumptuous Bedrooms: Ideal for family or group getaways.- Fully Equipped Gourmet Kitchen: Perfect for creating memorable meals and entertaining.- Elegant Living and Dining Areas: Designed for intimate gatherings and cherished moments.- Three Private Outdoor Waterfront Lounges: Revel in breathtaking ocean views and tranquil sunsets.- Ocean and Garden Views: Experience the harmony of serene ocean vistas and lush, tropical gardens.- Daily Housekeeping Service: Keeps your villa pristine and refreshed daily

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

Located in Islamorada, Florida, United States. Keys home overlooking the ocean and beautiful sunrises! Beautiful oceanfront residence with pool, and modern renovations. Located in desirable Islamorada with access to a private, sandy beach. A long private dock for fishing, with water dockage for 30 inch draft. In close proximity to restaurants, shopping and bars. View the Atlantic Ocean and sunrises from your balcony.

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.

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

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

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

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.