Vacation rentals in Florida Keys

4.91 out of 5 average rating, 385 reviews

The eco-friendly two-story River Queen vessel is anchored in a calm harbor, showcasing a modern design. The structure features large windows and a rooftop terrace, with a wind turbine on the left. The surrounding landscape includes lush greenery, complementing the serene water view.

Boat in Tavernier

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

4.98 out of 5 average rating, 221 reviews

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.

Home in Key Largo

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!!!

4.95 out of 5 average rating, 374 reviews

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Guest suite in Key Colony Beach

A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.

4.99 out of 5 average rating, 122 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

4.96 out of 5 average rating, 178 reviews

A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

4.97 out of 5 average rating, 183 reviews

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

Oasis2 in Key Largo With a million dollar view

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Vacation home in Key Largo

Two individuals wearing snorkeling gear are seen gliding through clear water above a coral reef, with a sea turtle swimming gracefully below. The underwater scene showcases vibrant coral formations and sandy sea floor, creating a serene marine environment.

4.89 out of 5 average rating, 273 reviews

6. Waterfront Key Largo Studio, Near Kayaks & Reef

Unwind in this Modern Key Largo waterfront studio, nestled on a canal with ocean access near Rodriguez Key, Mosquito Bank, and shipwrecks. Just minutes from John Pennekamp Park. Enjoy a full kitchen, ice-cold A/C, Smart TV, Wi-Fi, and assigned parking. Boaters can reserve our dock or use nearby Pilot House Marina. Snorkel reefs, kayak mangroves, or dine at local favorites like The Fish House, Sundowners, and Key Largo Fisheries. Comfort, adventure, and location in one perfect stay.

4.93 out of 5 average rating, 368 reviews

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

4.96 out of 5 average rating, 151 reviews

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

4.97 out of 5 average rating, 111 reviews

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

Condo in Key West

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.9 out of 5 average rating, 472 reviews

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Condo in Key Colony Beach

A spacious bedroom features a king bed with light bedding and decorative throw pillows. Large windows offer unobstructed ocean views and allow natural light to fill the room. A comfortable seating area is positioned nearby, facing the beach and tiki huts.

4.91 out of 5 average rating, 202 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated ground floor with a stunning, clean white interior and just a few steps from our private beach and heated pool. Continental Inn Unit #10 offers one King size bed that sleeps two people. A fully equipped kitchen with essentials (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Reliable WiFi and Smart TV.

Popular amenities for Florida Keys vacation rentals

Gym

Florida Keys beach vacation rentals

4.88 out of 5 average rating, 113 reviews

A row of townhomes is positioned along the water's edge, surrounded by well-maintained landscaping. Lush green trees provide shade, and the calm water reflects the serene environment. The horizon reveals a glimpse of distant trees and open water.

Condo in Duck Key

Villa 5027 on Duck Key BOAT SLIP available

4.85 out of 5 average rating, 142 reviews

An aerial view captures the scenic landscape of Key Largo, showcasing a coastline that merges crystal-clear water with lush greenery. Modern buildings line the marina, with boats gently moored along the waterfront, emphasizing the tranquil atmosphere of this resort area.

Townhouse in Key Largo

LIC. MGR. - 2/2 VILLA - OCEANFRONT BEACH RESORT!

4.86 out of 5 average rating, 106 reviews

A private balcony features a round table with four chairs, offering views of the expansive beach and Gulf waters. Clear blue skies and soft clouds create a serene backdrop, enhancing the coastal ambiance.

Condo in Marco Island

Apollo Beach Front! Sunset Views!Remodeled! 802

Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

4.94 out of 5 average rating, 109 reviews

The Lighthouse - Beach Houses Key West

4.91 out of 5 average rating, 185 reviews

The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.

Home in Marathon

Beachfront Villa - Florida Keys

A wooden pier extends over calm waters, leading toward a thatched-roof gazebo. The scene is illuminated by a vibrant sunset, casting warm hues across the sky and reflecting on the water's surface. Lush greenery frames the sides, enhancing the serene atmosphere.

4.97 out of 5 average rating, 102 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

4.9 out of 5 average rating, 109 reviews

Turtle Nest 1 Private beach,Pool, 2bed 2bath

A panoramic view captures the pristine turquoise waters extending to the horizon, adjacent to lush greenery and the resort's amenities. The interior showcases a bright, airy living space, featuring a well-equipped kitchen with modern appliances and a comfortable seating area with ocean views.

4.85 out of 5 average rating, 114 reviews

🏝 Oceanfront Paradise Awaits You

Private Florida Keys vacation rentals

4.95 out of 5 average rating, 59 reviews

A serene sunset casts warm orange and golden hues over the water, creating a calming reflection. The houseboat is visible with a cozy chair positioned towards the horizon. The surrounding calm waters and boats in the distance emphasize the peaceful setting.

Boat in Key West

Off Grid Boat "Shanty Pineapple" Key West

4.91 out of 5 average rating, 95 reviews

A balcony view reveals the expansive Atlantic Ocean, featuring a peir extending into the water. Palm trees are visible, adding a tropical ambiance. The serene blue waters and clear sky harmonize in the background, enhancing the coastal experience.

Condo in Key West

Ocean Front Studio private Sandy Beach in Key West

4.96 out of 5 average rating, 23 reviews

A coastal view features multiple white houses with balconies situated along the waterfront. Palm trees sway gently in the breeze, and clear blue skies create a serene backdrop. Vehicles are parked in the driveways, emphasizing accessibility to the beachfront.

Cottage in Cudjoe Key

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

4.98 out of 5 average rating, 531 reviews

Apartment in Key West

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

4.92 out of 5 average rating, 37 reviews

A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.

Houseboat in Marathon

b watervibe

4.95 out of 5 average rating, 73 reviews

A charming entrance is framed by lush tropical plants and palm trees. The light green door complements the inviting beige exterior of the home. A cozy seating area is situated on the porch, and brick pathways lead through a landscaped yard filled with vibrant foliage.

Condo in Key West

Vacation Home Heron Hideaway

Houseboat in Buttonwood Sound

A charming floating bungalow rests on calm waters, surrounded by an expansive horizon. Its thatched roof and large windows reflect a serene setting, while the gentle ripples of the water enhance the peaceful atmosphere.

5 out of 5 average rating, 22 reviews

Premium Floating Bungalow by Stay Ombi

4.96 out of 5 average rating, 24 reviews

A serene patio area showcases a private pool with illuminated edges, creating a calming ambiance. Outdoor furniture is arranged on a synthetic grass surface, framed by lush greenery and a tranquil water view, as the sky transitions to sunset hues in the background.

Home in Marathon

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Family friendly vacation rentals in Florida Keys

Tiny home in Big Pine Key

A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.

4.92 out of 5 average rating, 78 reviews

Cottage 30 min from Key West, free parking, pool

5 out of 5 average rating, 78 reviews

An outdoor dining area is presented with a rectangular table and six chairs, surrounded by lush greenery and serene water. A partially opened umbrella offers shade, while a compact air conditioning unit is positioned nearby on the rooftop surface.

Boat in Marathon

Dan’s 2024 catamaran cruiser vessel can’t be moved

A sandy beach area features numerous lounge chairs arranged in rows, each with a blue slatted design. In the background, a wooden pier extends over the water, surrounded by trees and calm waves under a clear sky.

4.89 out of 5 average rating, 155 reviews

1BR - Key Largo Sun & Sand Hideaway

4.96 out of 5 average rating, 55 reviews

The exterior of the cottage features a vibrant mural adorned with large floral designs, complemented by a light blue roof and shutters. Surrounded by lush greenery, the property sits on a textured gravel area under a clear blue sky.

Cottage in Islamorada

Waterfront Cottage Walk to World Famous Lorelei

4.66 out of 5 average rating, 29 reviews

An outdoor area features a large chessboard with oversized pieces set up on a sandy surface. Colorful lounge chairs and palm trees are visible in the background, alongside a glimpse of the ocean. Additional games can be seen in the vicinity, enhancing the recreational space.

Cabin in Marathon

Viamarhe Cabin-Private beach, Kayak, yard games

4.95 out of 5 average rating, 133 reviews

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.

Home in Key Colony Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

4.96 out of 5 average rating, 181 reviews

A serene view of a canal features lush palm trees lining wooden docks. A white boat is moored nearby, while a clear blue sky with scattered clouds reflects the peaceful surroundings.

Cottage in Key Largo

Charming Key Largo Cottage on the Water w/Kayaks!