Middle Keys vacation rentals

A calm waterfront scene is captured at sunset, showcasing a dock structure with a roof extending over the water. Soft hues of pink and purple reflect in the water, with palm trees and lush greenery framing the view, creating a serene ambiance.

4.98 out of 5 average rating, 502 reviews

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

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

A private hot jacuzzi is nestled under a sheltered area, surrounded by green foliage. Soft seating is positioned nearby, and natural light filters through the striped curtains. A staircase in the background leads to an upper level, while a wooden fence offers privacy.

5 out of 5 average rating, 11 reviews

Heron Hideaway

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

4.93 out of 5 average rating, 111 reviews

A covered deck features two lounge chairs with blue cushions, accompanied by a small round table. Lush green palm trees and tropical plants surround the area, while soft natural light filters in, creating a serene outdoor space for relaxation.

Condo in Key West

WALK TO BEACH, MALLORY SQUARE, DUVAL STREET

Key West a little piece of the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street. You're just a walk away from Zachary Taylor Park (where you can do yoga on the beach, swim, snorkel, or hang hammocks between the palms). We’re near numerous shops, restaurants, and museums. Enjoy coffee in the morning, wine at night on our oversized deck. THE ADJACENT UNIT MAY BE AVAILABLE FOR ADDITIONAL SPACE.

Houseboat in Stock Island

A clear swimming pool reflects the blue sky, surrounded by lounge chairs and umbrellas. Palm trees provide shade along the edge, complementing the vibrant greenery. In the background, modern multi-story buildings showcase balconies, offering a relaxed atmosphere by the water.

4.96 out of 5 average rating, 23 reviews

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

Superhost

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

4.8 out of 5 average rating, 270 reviews

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

4.97 out of 5 average rating, 259 reviews

Home in Key West

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Cottage in Little Torch Key

A long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Superhost

A serene private pool area is surrounded by lush tropical landscaping. Lounge chairs are arranged along the water's edge, inviting relaxation. A rock feature complements the pool, enhancing the natural ambiance created by palm trees and various greenery.

4.88 out of 5 average rating, 1,501 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. Located on a quiet street, it offers a private pool and peaceful stay for vacationers and business travelers. The unit includes a comfy Queen bed, mini fridge, microwave, iron & board, hangers, TV, and AC. Enjoy Key West's warm weather year-round. This special place is close to everything, making it easy to plan your trip. Just a heads-up: Key West’s famous roosters love to strut and crow—part of the island charm!

4.97 out of 5 average rating, 100 reviews

A wooden pier extends into calm waters, leading towards a beach with soft golden sand. In the background, a multi-story building is nestled among palm trees, set against a sky with scattered clouds and a single bird in flight.

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.

5 out of 5 average rating, 10 reviews

A serene outdoor area is highlighted by a clear blue salt-water pool surrounded by lounge chairs. Palms sway gently in the breeze, and a dining table sits nearby. The water view invites a sense of tranquility, complemented by landscaped greenery along the perimeter.

Townhouse in Key West

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.

A charming entrance is revealed by a white picket fence, leading to a lush, landscaped pathway bordered by tropical greenery. A spacious patio area with dining furniture is visible under a large awning, while the upper balcony invites relaxation among the palm trees.

4.96 out of 5 average rating, 280 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

Superhost

A tranquil beachfront scene showcases a sandy shore lined with palm trees. Calm waters reflect the sky, dotted with fluffy clouds. In the distance, a marina displays boats alongside wooden docks, while cozy thatched-roof structures provide shaded seating.

Houseboat in Key West

4.87 out of 5 average rating, 246 reviews

Key West Luxury Houseboat at Yacht Club Resort

2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath PANORAMIC Ocean Views 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, HUGE SKY Deck Rooftop Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

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Popular amenities for Middle Keys vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Middle Keys

4.95 out of 5 average rating, 19 reviews

Two wooden chairs provide seating on the deck of the houseboat, facing the open waters of Key West. Large glass doors lead into the kitchenette area, with a view of the serene sea and sky, emphasizing the peaceful outdoor setting.

Houseboat in Key West

Shanty Pineapple Key West

KirstieRating, 5 stars1 week ago

Thanks to Tony for making our stay at the Shanty Pineapple was a wonderful experience! Everything was clean and how it was described in the listing! We had a great time celebrating our anniversary! The view of the sunrise and sunset each day was amazing! And the food delivery was extremely convenient! Thanks again Tony! Highly recommend!

4.93 out of 5 average rating, 174 reviews

A serene pool area is surrounded by lush greenery and wooden fences. Several lounge chairs are positioned on the deck, along with a shaded umbrella offering a space for relaxation. The water glistens under the sun, inviting guests to enjoy the tranquil atmosphere.

Private room in Key West

Nuns Room, A single travelers delight!

RobertRating, 5 stars1 week ago

I stayed in the Nun's Room. The room's here all have names instead of numbers. It was a small room (and a small bed) on the second floor, no extra frills going on, but nice enough. The bedside clock had an issue with its display so I could not set an alarm on it. I just used my cell phone to wake me up in the morning. Breakfast was provided. Like the room, it was nice enough. The host was friendly to me at check in. Check out went smoothly.

A bright living space features large windows with light-filtering shutters, offering a view of the outside. A spacious day bed is positioned near the windows, complemented by a rustic dining table and chairs. The adjacent kitchen includes modern appliances, enhancing the open layout.

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars2 weeks ago

The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

5 out of 5 average rating, 32 reviews

A stately Victorian mansion is framed by lush greenery and tall palm trees. Bright orange shutters contrast with the white exterior, and the intricately detailed porch adds charm. The inviting entrance is accented by potted plants, creating a warm welcome to guests.

Hotel room in Key West

Marrero's Guest Mansion Adult Only (21+) Room 7

ChristinaRating, 5 stars1 month ago

Just what we were looking for! Clean, quiet, convenient and walkable to everything. Loved the pool area. Hosts were all friendly, welcoming and helpful. Would stay here again.

5 out of 5 average rating, 6 reviews

A shared parking area features several vehicles, including a silver sedan, a white jeep, and a bright red sports car. Tropical palm trees and green foliage surround the space, and the pastel-colored buildings in the background add visual charm to the setting.

Condo in Key West

Parking, Deck, Pool, Beach, 2 Blocks to Duval St

JamieRating, 5 stars1 month ago

Karen’s place is the PERFECT home for your stay in Key West! The location couldn’t be more ideal, right in the heart of all Key West has to offer and yet so private and quiet. The space was recently renovated and in great condition. Having a washer/dryer in the unit is a huge bonus. Kitchen has all amenities. Karen is an excellent host, quick to respond and willing to offer local suggestions. We would absolutely stay here again!!

4.98 out of 5 average rating, 42 reviews

A wooden deck extends outward over clear blue water, framed by large sliding glass doors. Palm trees sway gently in the breeze, with boats seen docked in the background along the marina.

Boat in Key West

Waterfront & Heated Pool - Awai's Floating Villa

ChelseaRating, 5 stars1 week ago

We stayed from Sunday to Friday and had an incredible time! The location was perfect—just a short drive to all the excitement of Key West, yet tucked away enough to feel peaceful and relaxing. The houseboat was spotless, cozy, and a perfect fit for our family of four. It had everything we needed for a comfortable stay. The resort itself was stunning, and the pool was the perfect way to unwind after a full day of exploring. The neighbors were so friendly, and the entire community had such a welcoming vibe. We would absolutely recommend this spot to anyone looking for a unique and relaxing getaway—and we’re already planning our next visit!

Several Aqualodges are anchored in calm waters, featuring light-colored exteriors with blue accents. Each Aqualodge is equipped with outdoor seating arrangements, including white chairs, creating inviting spaces for relaxation on the deck under clear skies.

Houseboat in Key West

4.74 out of 5 average rating, 190 reviews

Deluxe Bungalow

BradleyRating, 5 stars1 day ago

Aqua lodges were exactly as described and just what we needed. The value was great and we had a blast staying there. Marina restaurant was really good too.

A private balcony overlooks palm trees, providing a serene retreat. Glass doors open to the interior space, revealing a brightly lit area containing a bed and decorative furnishings. A small table and chairs adorn the balcony, inviting relaxation.