House holiday rentals in Key Largo

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, 176 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!

An aerial view of a spacious pool surrounded by lush greenery and palm trees. The pool features a unique, winding shape, with several lounge chairs arranged around the perimeter and shaded spots provided by umbrellas.

4.93 out of 5 average rating, 148 reviews

Mariners Club Resort, Best in the Upper Keys

SPACIOUS AND STUNNING Family Friendly 4+ br home. One of the few to allow 10 guests! POOLS w/ hot tubs MARINA for direct access to reef; diving, snorkeling, fishing & sandbars KAYAKING Pennekemp DISCOUNT to swim with dolphins at DPMMR ACTIVITIES; tennis & pickleball courts, gym & game room. LOCATION: restaurants, bars, grocery and other conveniences PARKING for two cars on site WE ARE LOCALS who know the importance of family time so look no further than this special slice of paradise!

Aerial view of a waterfront community featuring multiple homes surrounded by lush greenery. Two circular pools are visible in the foreground, with docks extending into the water. A sailboat is seen on the horizon, showcasing the serene setting.

4.96 out of 5 average rating, 112 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Large Waterfront home completely renovated in gated upscale community. 2/2 upstairs and complete efficiency downstairs. You're 12 houses away from the Bay and near many restaurants and attractions. BRAND NEW POOL along with new GAZEBO and BBQ area (Not shown it some pictures). Enjoy sunset cruises, island hopping and dock-side dining. 60' of waterfront, large dock and 2 kayaks available. Ask me about discounted pontoon rental rates, to be used bay side only. Must be 25 or older to book.

4.93 out of 5 average rating, 122 reviews

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.

Home in Key Colony Beach

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.

A calm waterway is flanked by thatched-roof structures on either side, surrounded by lush palm trees. The clear blue sky reflects on the still water, establishing a serene atmosphere. The scene invites opportunities for boating and leisure activities.

4.81 out of 5 average rating, 101 reviews

Paradise Found-Key Largo Kampground Divers Welcome

2 bedroom, home in Key Largo Kamp ground with use of all amenities. Spacious lush, tropical patio, great for entertaining. Wifi -cable & 50" smart tv in LR 32” smart tv BR. House is stocked with everything you need to cook meals or enjoy the outstanding restaurants Key Largo has to offer. Has heated pool, boat ramp, laundry facilities, play ground, 2 small beaches. Close to shopping, great restaurants, scuba diving, boating, fishing, houses of worship. John Pennekamp State park 1 mile away.

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.

4.99 out of 5 average rating, 217 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!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

4.97 out of 5 average rating, 204 reviews

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.

Home in Islamorada

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.

4.98 out of 5 average rating, 128 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.

4.9 out of 5 average rating, 109 reviews

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

NO RESORT, GUEST OR MANAGEMENT FEES WHEN BOOKING MY HOMES! Welcome to your Key Largo vacation rental. This oceanside villa is family friendly and filled with amenities, including a private golf cart, one adult kayak and three kids kayaks, pickleball and tennis courts, multiple pools, and a unique swimming lagoon. Spend your days kayaking, fishing, boating, snorkeling, or the beach John Pennekamp. Our villa has earned hundreds of 5-star reviews on all major platforms. No hidden fees!

4.97 out of 5 average rating, 172 reviews

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

This waterfront retreat is perfect for couples, families, or boaters looking to explore the best of the Keys. Snorkel right from the dock, paddle through mangroves with the tandem kayak, or relax with a drink while the sun sets over the canal. Steps from two heated pools, a playground, and a sandy beach, plus only 0.3 miles from groceries and restaurants. Whether you’re fishing, diving famous reefs, or just unwinding under the tiki, this home puts paradise at your doorstep.

An aerial view of the waterfront area shows vibrant turquoise waters and lush greenery. The scene includes several residential buildings along the coastline and a nearby marina, with boats visible on the water and the horizon illustrating a scenic expanse.

4.93 out of 5 average rating, 215 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! 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 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, 179 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 house rentals in Key Largo

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 189 reviews

A shaded outdoor seating area features a hanging chair, a small table, and decorative lanterns. The pool is visible in the background, surrounded by a well-maintained garden and sun loungers. The space is designed for relaxation, with ample natural light filtering through.

Home in Miami Springs

Spanish House 3 Bedroom Pool House

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

4.99 out of 5 average rating, 158 reviews

Cancellation Deal: March 21 thru March 28

4.96 out of 5 average rating, 156 reviews

A refreshing outdoor pool is framed by palm trees and a surrounding patio of laid stones. Two loungers are positioned partially submerged in the water, complemented by a large umbrella for shade. The clear sky is visible above.

Home in Cutler Bay

King Bed Home by the Bay FAST WI-FI & Coffee

The outdoor space features a tropical-inspired saltwater pool with a unique shape, surrounded by natural stone decking. A thatched-roof tiki hut is visible nearby, along with a dining table and lounge chairs, creating an inviting area for relaxation and leisure.

4.93 out of 5 average rating, 426 reviews

Private Paradise between Miami & the Keys

A shaded tiki hut is situated on a stone patio beside a tranquil canal. The space is furnished with a table and chairs, surrounded by palm trees. Brightly colored kayaks are neatly arranged on a nearby dock, adding to the outdoor ambiance.

4.9 out of 5 average rating, 105 reviews

*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes

A bright living room features a large beige sectional sofa facing a glass coffee table. A decorative piece rests on the table, while a tall indoor plant adds greenery. Sunlight streams through expansive windows draped with sheer white curtains, illuminating the white walls and marble flooring.

4.87 out of 5 average rating, 103 reviews

Tropical Paradise Between Miami and the FL Keys

4.94 out of 5 average rating, 109 reviews

A private pool area is surrounded by lush greenery, featuring a mosaic-tiled pool reflecting vibrant colors in the water. Two woven lounge chairs are positioned nearby, inviting relaxation. The sky showcases a blend of warm colors at sunset, enhancing the serene outdoor setting.

Home in Miami

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ

5 out of 5 average rating, 20 reviews

A spacious outdoor area features a heated pool with a jacuzzi nearby. Comfortable seating arrangements are set under a shaded area, and a screened-in patio provides additional protection from the elements. Lush greenery surrounds the pool area, contributing to a relaxed atmosphere.

Home in Tavernier

Superb Keys home w/heated pool

Weekly house rentals

5 out of 5 average rating, 10 reviews

King Bed • Spacious • Boutique-Style Stay

A cozy living area features a dark sectional sofa adorned with decorative ocean-themed pillows. A light-colored coffee table sits in front, complemented by a comfortable chair. A wall-mounted television is positioned in the corner, enhancing the space with soft natural light from the windows.

4.89 out of 5 average rating, 18 reviews

Key Largo Beach Getaway

A charming building is surrounded by lush palm trees, positioned adjacent to a sandy beach area. A wooden dock leads from the water's edge towards the building, providing a scenic pathway. The structure features a metal roof and a welcoming porch area.

4.74 out of 5 average rating, 191 reviews

BayFront Cottage,Bay Front Porch,Central AC,Beach

The exterior of the charming waterfront home showcases a two-story structure painted in soft green. A spacious deck surrounds the upper level, while palm trees provide shade. The gravel landscaping highlights the elevated foundation, with a separate set of stairs leading to the entrance.

4.93 out of 5 average rating, 40 reviews

Keys Paradise 3/3 Waterfront, Jacuzzi, Kayaks+More

The outdoor area features tiki lights strung above a sandy space, surrounded by tropical plants and palm trees. A casual seating arrangement includes a fire pit, inviting relaxation under the evening sky. The ambiance is enhanced by soft lighting and natural vegetation.

4.94 out of 5 average rating, 33 reviews

Keys Cabin #218

5 out of 5 average rating, 8 reviews

Home in Islamorada

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

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, 100 reviews

Great key Largo home with water front and pool

5 out of 5 average rating, 8 reviews

Two wooden lounge chairs are positioned on the dock facing a wide canal. Lush palm trees line the shore, and several boats can be seen moored along the water, with bright blue skies and scattered clouds overhead.

Home in Key Colony Beach

Boat Dock, Cabana Club, Paddleboard, Ground Level

Private 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, 41 reviews

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

A private pool area features a rectangular water space surrounded by lounge chairs and large umbrellas. Lush greenery encloses the yard, while playground equipment is visible in the background. The sky displays a colorful sunset, adding a serene ambiance to the setting.

4.98 out of 5 average rating, 66 reviews

5 out of 5 average rating, 23 reviews

A resort-style swimming pool is surrounded by lush palm trees, offering a relaxing atmosphere. Comfortable lounge chairs are positioned around the pool, with tranquil ocean views in the background. Clear blue skies complement the serene setting, suggesting an inviting space for leisure.

Home in Islamorada

Pristine pool front home w/ocean views Anglers 148

5 out of 5 average rating, 9 reviews

KCB Tropical Escape

A modern living area is shown with a large sectional sofa and a sleek black coffee table. A ceiling fan spins gently above, while a wall-mounted TV is positioned against a striped accent wall. Glass doors frame views of the pool area, allowing natural light to fill the space.

5 out of 5 average rating, 4 reviews

Tropical 2BR/2BA Getaway in Gorgeous Key Largo

4.9 out of 5 average rating, 72 reviews

The Dream Studio

5 out of 5 average rating, 31 reviews

An open living space is featured, highlighted by a round dining table surrounded by comfortable seating. A large television is mounted on the wall, while light-colored walls enhance the bright atmosphere. A serene coastal artwork depicting a pier adds a calming touch to the decor.

Home in Key Colony Beach

Bohemian Beach Bungalow

An aerial view captures a spacious lagoon-style pool surrounded by palm trees, with deck chairs positioned for relaxation. The pool seamlessly merges with the ocean, offering tranquil blue waters against a backdrop of lush greenery and the distant horizon.