58,368 properties available

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.

Located in Islamorada, Florida, United States. 4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef! Island Villa Rental Properties offers Seas The Day in Islamorada, Florida Keys. Seas the Day is a fun, 4 bedroom house set on Lower Matecumbe Key in the beautiful Islamorada. On visiting the property, you ll first notice that it s just 3 small lots away from the Atlantic Ocean, and almost a straight shot to Alligator Reef Lighthouse (some of the most iconic snorkeling and fishing in Islamorada).On the bottom level, you’ll find the master bedroom, and kids bedroom, with a bunk bed and two separate twin beds. There is also a large flat screen for the living room, and a separate TV in the den with views throughout. All TV s come with cable and there is an Apple TV in the living room, please bring your own streaming information.Moving outside, you’ll see the splash pool with the sun deck and a few hammock chairs for afternoon sun naps. Check out the video in the videos section to truly get a feel of the complet

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

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

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

Located in Islamorada, Florida, United States. Oceanview Villa at The Islands of Islamorada: Tropical Bliss & Resort Amenities Welcome to The Islands of Islamorada Resort: Your Tropical Paradise Awaits!Experience the perfect blend of coastal charm and luxury at The Islands of Islamorada, where your dream tropical getaway becomes reality. Nestled in the heart of the picturesque Florida Keys, our three-story waterfront villas offer an unparalleled escape for families and friends seeking both relaxation and adventure.Accommodations:Step into a world of comfort and elegance with our beautifully appointed villas, each boasting:- Four Spacious Bedrooms: Perfect for family or group getaways.- Fully Equipped Kitchen: Whip up your favorite meals or entertain with ease.- Inviting Living and Dining Areas: Designed for creating cherished memories together.- Three Outdoor Waterfront Lounge Areas: Enjoy breathtaking ocean views and serene sunsets.- Ocean and Garden Views: Enjoy tranquil ocean and lush garden views from your villa, blending sere

Located in Islamorada, Florida, United States. Spacious Caribbean-Style Home w/ 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 that

Located in Islamorada, Florida, United States. Lush Garden Estate in Islamorada FL, W/ Pool, Dockage, Ocean Front & great views Island Villa Rental Properties offers this 3 bedroom home with a one bedroom guest house, rents all as one. Located on the Ocean side with lovely pool and dock.Located near Morada way in the ‘Heart of Islamorada.’ Quietly located on the old road, walk or ride bikes to breakfast, lunch, dinner and festivals! A favorite for full moon partygoers or restauranteurs.Dockage is fantastic for sunrises and views. Keep an eye out for beautiful wild life or do some light flats fishing straight from the dock. Keep an eye out, and you’ll see something fantastic every trip!Well kept gardens show off the lush beauty of Islamorada. Or sit on the ocean front bar and eat dinner. There is a reason people love this estate…Pool conveniently located on the ocean front pool deck so you can have both-- see the photos, truly relaxing. Sorry, no pets.Rates: Holidays, Spring Break, and Mini Season are priced at $8,000 Weekly

Located in Islamorada, Florida, United States. Beach Oasis: Pool, FREE Parking, Water Activities Onsite! Close to Founders Park 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 t

Located in Islamorada, Florida, United States. This is The Oasis, YOUR private Oasis! The Oasis - This majestic property is over 2.75 acres of landscaped beauty. There is more white sand on this lot than any in all the keys! The palm trees are some of the tallest as well and their graceful presence puts you in the Jimmy Buffett mode as the cooling Atlantic Ocean winds blow your hair and alleviate the heat. When you relax in the pool, the view of Alligator Reef Light on the horizon and the boats going by provide a backdrop while sipping your margaritas. Never worry about a crowed beach or people kicking sand on you while you sun yourself. Swim in the crystal blue water or stay on top with our kayaks and paddleboards for exercise. Consisting of two homes, the main is one bedroom one and a half baths and the other is two bedrooms and one bath, each with a kitchen and living room. Amenities include your private heated salt-water pool, 4 kayaks and 2 paddleboards among other items. Pet friendly and in the HEART of Islamorada on Upper Ma

Located in Islamorada, Florida, United States. Cute & Cozy 3 Bedroom Canalfront Pool Home 137 Cortez Drive - The dream home away from home. The upstairs main floor offers two large bedrooms with cozy king beds, two full baths, a beautifully decorated open concept living and dining room, updated kitchen and great outdoor living area. Pool and canal views from not only the expansive screened-in balcony, but also from the cute and comfy sundeck. The downstairs guest quarters offer a simple and separate kitchen, dining and living room, large bedroom with two double beds and bathroom. With a large pool, outdoor seating areas, lounge chairs, grill, dockage and luscious landscaping, this property has the ultimate backyard experience for a perfect vacation.If booking more than a year in advance current prices may not reflect the annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with you. Please note: before proceeding with your booking, kindly revie

Located in Islamorada, Florida, United States. Short Distance From The Well Known Sites! Pool, Free Parking, Pets Allowed 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 card p

Located in Islamorada, Florida, United States. Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required) This is a quaint, ocean side condo with full amenities and easy access for fishing, diving, snorkeling and much more.The apartment sleeps 2-4. It has a king bed in the bedroom, a pull out sofa bed in the living room, a fully equipped kitchen, a garage with additional fridge/freezer. Boat/trailer storage in boat yard included on availability and easy ramp access. Fish cleaning table and BBQ grill also on property.There is an ocean of things to do for everyone. Shopping, Keys themed restaurants both inexpensive and high-end all over the islands. There is swimming, tennis, pickle ball, snorkeling, diving, bird watching, historical interest, botanical, culture, kayaking, wildlife and pondering life. The property is a nature lovers dream with an occasional manatee in the canal, iguanas that sun themselves on the dock, pelicans, egrets and osprey that fly in for a hello there.We can accommodate a registered 25 ft b

Located in Islamorada, Florida, United States. Seaside Serenity: 3 Spacious Villas Steps to Whale Harbor Marina. FREE 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 ty

Located in Islamorada, Florida, United States. Your Keys Getaway - A A beautiful home on the bay, in sunny Islamorada, Florida. You have access to one of the only beaches in Islamorada, which is a quarter mile from the house. A quick boat ride and/or key access if you’d like to travel by car. Dock space has over 60 feet with your own personal ramp (ramp only accommodates smaller boats, 3,000 pounds or less). Amazing bay sunsets and gorgeous ocean side sunrises. This property is two separate units, listing for first floor only. You can access all common areas, dock, ramp, laundry unit, parking, and sitting areas.Smaller pets are welcome under 40lbs, as long as you clean up after them and keep off furniture.