House holiday rentals in Islamorada

5 out of 5 average rating, 10 reviews

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Welcome to Anglers Reef, a bright coastal cottage in Islamorada, FL, with access to resort-style amenities. Enjoy a private boat slip, tropical pool, sandy beach, and walkable marina. Inside, relax in open living spaces, a fully equipped kitchen, and serene bedrooms. Unwind on breezy porches or explore nearby snorkeling, fishing, dining, and Keys adventures. Ideal for families, couples, and boaters seeking laid-back luxury. Thoughtfully designed for comfort, privacy, and effortless island life.

A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.

4.98 out of 5 average rating, 230 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

A collage showcases four images: A serene sunrise over water, a cozy bedroom with a flat-screen TV, an open-concept living area with a kitchen and dining space, and a tranquil view of the evening sun reflected on the bay, complete with a kayak along the shoreline.

4.9 out of 5 average rating, 182 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

5 out of 5 average rating, 4 reviews

FL Keys Ocean Front Escape

Welcome to FL Keys Ocean Front Escape in beautiful Islamorada! This 2-bedroom, 3-bathroom retreat offers stunning ocean views and all the comforts of home. Enjoy essentials like WiFi, air conditioning, a fully equipped kitchen, and a washer. Relax in paradise with the perfect blend of modern amenities and tropical charm. Experience 360' views of the finest Islamorada sunrise from the private roof top deck! Whether you're fishing, snorkeling, or just unwinding, your dream getaway starts here!

A spacious deck is visible, offering a view of the Gulf of Mexico and a nearby dock. Comfortable outdoor seating is arranged against the backdrop of lush greenery and a sandy shoreline, providing a relaxing setting to enjoy the scenery.

4.82 out of 5 average rating, 108 reviews

Beautiful Waterfront book now 2026 filling up fast

This property is like having your own private resort. We are on the Gulf of Mexico with a Million-dollar waterfront view & sunsets. 4BR + bonus room w/queen bed & futon. 2 full bathrooms 4 TVs. Pool, Private Dock. Watch the Dolphins daily. We a located next to the World-Famous Dolphin Research Center. House has wrapped around deck plenty of seating inside/out. Large private yard with plenty of room for all your needs. Walking distance to restaurant, marina. Kayaks/Paddleboards mostly available.

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

4.92 out of 5 average rating, 129 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.

4.97 out of 5 average rating, 206 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

An aerial view of a blue, two-story house surrounded by greenery. The backyard features a swimming pool, red umbrellas, and seating areas. A patio leads to the pool, and the front yard is landscaped with grass. The neighborhood shows a quiet street with nearby houses.

4.99 out of 5 average rating, 138 reviews

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.

✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

4.94 out of 5 average rating, 16 reviews

Islamorada Bungalow # 5

Bring the whole family to this great place with lots of room for fun.Escape to our charming 2-bedroom, 1-bathroom bungalow in Islamorada, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing. Whether you seek adventure or relaxation. Secure your stay now for an unforgettable experience!

4.93 out of 5 average rating, 208 reviews

Two glasses of red wine are positioned beside a bottle of 14 Hands Cabernet Sauvignon. The scene is set against a bright ocean view with palm trees swaying gently. The turquoise water enhances the serene atmosphere, inviting relaxation.

Home in Duck Key

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.

4.95 out of 5 average rating, 112 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

A two-story duplex is set amidst palm trees, featuring a blue exterior and multiple balconies. A vehicle is parked in the driveway, with a pathway leading towards the entrance, surrounded by landscaped areas that include gravel and greenery.

4.92 out of 5 average rating, 185 reviews

Blue House Marine in Key Largo

The house is a Duplex style house for guest it is very quite and private it has 3 bedrooms and two bathrooms kitchen living room and dining area also a walk around balcony its screen in, it has 2 queen style beds and two twin beds. the home has been remodel you have canal views and open ocean viewsfull bathroom by the pool, barbecue area table and chairs for dining plus out door furniture. P.S There is no longer pool heating

Popular amenities for Islamorada house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view shows the property in proximity to the Atlantic Ocean, surrounded by palm trees. A dock extends into the clear water, with the colorful buildings of the surrounding area visible. The scene captures a serene coastal landscape, enhancing the appeal of a beachfront getaway.

4.89 out of 5 average rating, 9 reviews

Keys to Ohana. Ocean views. Private Pool, Hot Tub

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 64 reviews

Marathon Keys Escape • Pool • Hot Tub • Near Beach

An aerial view shows a single-story house with a light grey metal roof situated along a canal. The building features a patio area surrounded by palm trees. Nearby homes and a dock with palm trees lining the waterway are also visible, indicating a tropical environment.

4.94 out of 5 average rating, 51 reviews

Waterfront House - 30' Dock & Pool at Cabana Club

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

4.94 out of 5 average rating, 135 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

The outdoor area showcases a private heated pool surrounded by lounge chairs. Lush greenery is present, along with a staircase leading to the upper level of the home. The canal is visible in the background, with boats moored along the dock under a clear blue sky.

4.93 out of 5 average rating, 15 reviews

*NEW!*Paradise Palms~Dock~Pool~Kayaks Grill~View!

4.9 out of 5 average rating, 112 reviews

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks

An aerial view showcases a canal front home with a pool and spacious deck, surrounded by palm trees. Two neighboring homes are visible along the water's edge, highlighting the serene and scenic environment.

4.9 out of 5 average rating, 103 reviews

Great key Largo home with water front and pool

5 out of 5 average rating, 3 reviews

Bayview Beautiful townhouse in Islamorada, FL KEYS

Weekly house rentals

A spacious outdoor area is surrounded by tropical landscaping, featuring a BBQ grill and a hot tub. Comfortable lounge chairs are available under umbrellas, with a gravel walkway leading to various seating arrangements. Sunlight filters through the palm fronds, creating a relaxing atmosphere.

4.95 out of 5 average rating, 44 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

4.85 out of 5 average rating, 13 reviews

P98 - 75ft dock with shore power, 4 bed, 4 bath ho

5 out of 5 average rating, 48 reviews

Heated Pool w/4 water loungers/CabanaClub/ 6 Bikes

5 out of 5 average rating, 8 reviews

Home in Duck Key

Blue Waters Stay - 2BR 2.5BA Coastal Villa

A sandy beachfront is framed by palm trees, with the glistening Atlantic ocean in the background. A volleyball net is set up on the sand, along with multiple seating areas for relaxation, inviting guests to enjoy the tranquil environment and scenic views.

4.91 out of 5 average rating, 45 reviews

Viamarhe House-Private beach, Kayak, yard games

An outdoor theater area is outlined by a modular seating arrangement with blue cushions and dark wicker. A large projection screen is mounted on a wooden wall, creating an inviting space for movie nights. Soft lighting from overhead strands completes the ambiance.

4.92 out of 5 average rating, 39 reviews

Oceanview Marathon - Screened Porch, Theater & Bar

An aerial view showcases a waterfront property featuring two light-colored homes. A manicured green lawn, lined with palm trees, leads to a private boat slip. A spacious covered area offers an outdoor seating arrangement, enhancing the outdoor living space near the water.

4.91 out of 5 average rating, 32 reviews

Waterfront Paradise Key Largo. Casa Luna

A spacious living area features a plush sectional sofa, a light-colored throw draped over the arm, and a flat-screen TV mounted on a wooden accent wall. Natural light filters in through sliding glass doors, illuminating a dining table and additional seating in the background.

4.95 out of 5 average rating, 61 reviews

Ocean Shores Villa 1 with Pool and Boat Slip

Private house rentals

The exterior of a charming waterfront home is depicted, showcasing a canal with clear turquoise water. Lush palm trees frame the property, and well-maintained landscaping adds to the serene environment. The two-story building features a spacious porch and multiple balconies, enhancing outdoor living.

4.96 out of 5 average rating, 72 reviews

Coral Lagoon #23- Private Villa Home

A serene outdoor area features a heated pool surrounded by lush greenery and palm trees. Two chaise loungers sit on a small patch of grass, offering a perfect spot for relaxation. The ocean is visible beyond the white fence, enhancing the tranquil setting.

5 out of 5 average rating, 55 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

4.92 out of 5 average rating, 50 reviews

Florida Keys Oceanside Utopia

A private pool is surrounded by a paved patio, featuring lounge chairs and a small table. Lush tropical plants provide a natural backdrop. In the distance, a boat dock is visible along with outdoor dining furniture and an umbrella. Soft lighting enhances the inviting outdoor space.

5 out of 5 average rating, 19 reviews

Waterfront home w/pool, dock & close to beach

A private pool area is surrounded by palm trees and greenery, featuring a swimming pool and an oversized spa. Bright green lounge chairs are placed around the pool, complemented by shaded umbrellas. The exterior of the two-story home is painted in a cheerful blue, contrasting with the natural surroundings.

4.95 out of 5 average rating, 94 reviews

Casa Solaris | Key Largo home with Private Pool!

5 out of 5 average rating, 11 reviews

Casa De Grouper with a Beautiful Canal View

A private deck overlooks lush greenery leading to the ocean. A circular table with six chairs sits under a large umbrella, providing a shaded spot. The scene features bright blue skies and a calm sea, creating a serene atmosphere.

5 out of 5 average rating, 62 reviews

Oceanview Escape