Vacation rentals in Fleming Key

5 out of 5 average rating, 8 reviews

A paved driveway features two parked vehicles, flanked by tall palm trees and lush tropical plants. A wooden white picket fence creates a welcoming entrance, with the bright blue exterior of the condo visible in the background, surrounded by greenery.

Condo in Key West

Coral Palms 1BR/King/Queen, Pool, block to Duval

Escape to this charming 1BR, 2nd-floor condo in the heart of Historic Key West. Sleep soundly in a plush king bed and additional guests in a Queen & sofa bed in a spacious living area and a fully equipped kitchen. Lounge poolside under the palms, grill, or relax in the refreshing pool. No transportation needed, you're just steps from lively Duval Street, world-class dining, nightlife, and beaches. Perfect for a romantic getaway or a fun retreat, your island escape awaits! Hosted by Nautipussy!

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.

Vacation home in Key West

A charming garden pathway is lined with lush tropical foliage, leading to a colorful green cart among vibrant plants. The surrounding trees provide a natural canopy, creating a serene atmosphere in this verdant outdoor space.

4.87 out of 5 average rating, 322 reviews

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

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.

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.

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, 21 reviews

Two white chairs are positioned on a striped red and white deck, providing a cozy seating area. Sunlight reflects off the nearby water, and a canopy shades the upper deck in the background under a bright blue sky with scattered clouds.

Boat in Key West

“The Easy Way” Comfy, Practical, Convenient

Reconnect with nature at this unforgettable escape. Stay off Key West away from the crowds and listen to nature. Vessel “Easy Way” is perfect for up to 2 people. Come enjoy the amazing sunrise and sunset. Cook out on the balcony, watch fish, birds, stingrays, and dolphins go by. Vessel Easy Way has an outdoor shower, paddle board, and outdoor grill. This floating home is perfect for people who want to relax and enjoy nature.

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).

4.87 out of 5 average rating, 246 reviews

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

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 Fleming Key vacation rentals

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Other great vacation rentals in Fleming Key

4.86 out of 5 average rating, 22 reviews

A white wooden sign displays the words 'Garden House' surrounded by lush green foliage. Tropical plants and palm leaves frame the sign, creating a serene and inviting atmosphere in the outdoor setting.

Private room in Key West

Garden House Queen Room

RussRating, 5 stars3 weeks ago

Amazing stay and even better than expected. The room was quaint and everything we needed. Close enough to walk everywhere. The amenities were great. I had forgotten there’s a little pool and that was a great treat after a long day in the sun. We’re already looking to book again!

4.9 out of 5 average rating, 153 reviews

A peaceful outdoor area features a blue swimming pool surrounded by lounge chairs. Lush greenery and tropical plants create a natural barrier, while a wooden lattice fence offers privacy. A sun umbrella provides shade for guests enjoying the poolside space.

Private room in Key West

Pink - 1 Queen bed, Shared bathroom

DagoRating, 5 stars4 days ago

I still gave a 5 although we had some issues checking in. The wrong key was provided at check-in; however they handled the hiccup quickly and timely. The location is close enough to all the action. The B&B is well stocked and they thought of everything to make your stay comfortable.

5 out of 5 average rating, 9 reviews

Private room in Key West

Duval street downtown

VictoriaRating, 5 stars5 days ago

I loved staring at Juan’s place and will definitely stay here again if I am in Key West. His place is just south of all of the popular bars on Duval Street, which is nice because you’re close enough to the party scene but still pretty far away. I was able to get great sleep and the surroundings weren’t loud at all although there is a restaurant downstairs that plays music until midnight however, Juan provides earplugs, and I did not hear it or have any issues with the music. You can tell that he put a lot of thought and detail into the space such as sleep masks, chargers, full length mirror and a variety of soaps to choose from during your stay. Before I arrived, he sent me instructions, including a video on how to find this place which was spot on. He even has bikes that you can use during your stay which was awesome. I love riding bikes, so this was definitely a highlight of my trip! Thank you Juan for your hospitality!

A stately Victorian house is surrounded by lush greenery and tropical palm trees. The exterior features bright orange shutters and a welcoming front porch with decorative railings, providing an inviting entrance amid the vibrant foliage.

4.98 out of 5 average rating, 43 reviews

Marrero's Guest Mansion Adult Only (21+) Room 12

LoriRating, 5 stars3 weeks ago

Great place to stay! Everyone was super friendly and very helpful. Location is great. Able to easily walk and explore the area and then come back and relax in a quiet setting. Loved the breakfast offered daily and all the amenities. Definitely would stay here again.

An outdoor pool is surrounded by vibrant palm trees and colorful flowers. Stylish lounge chairs with bright cushions are positioned around the water. A covered seating area offers shade and relaxation, creating a welcoming space for guests to enjoy the sun.

4.67 out of 5 average rating, 113 reviews

Coastal Comfort | Sunset-watching. Outdoor Pool

JannetRating, 5 stars2 weeks ago

I can't understand all the negative reviews on Google Maps at all. The hotel was as advertised, it was clean and the staff were friendly. The only thing that bothered me was the volume from outside, because the balcony door doesn't really lock (not well sealed). But otherwise everything was perfect! The fees are transparent and you will be informed in advance. The shuttle was a good way to get into town.

4.91 out of 5 average rating, 313 reviews

A unique tiki suite floats on calm waters, featuring a thatched, curved roof that adds character. The accommodation is open on the sides, offering unobstructed views of the serene landscape and sky during sunset.

Boat in Key West

Tiki Suites ~ The Grand Tiki

JonathanRating, 5 stars3 weeks ago

The tiki was incredible, we had ama amazing time. The only thing is that the tiki is not 20 minutes from the dry tortuga national park, we had to go by sea plane because the timing of shuttle to and from the tiki did not allow to use the ferry. Regardless the tiki experience itself was really incredible just make sure to add in the expenses for the shuttle back and forth.

4.76 out of 5 average rating, 335 reviews

Newly renovated + Free Full Breakfast - King Bed

Rosemary HelenRating, 5 stars2 weeks ago

Very good experience overall! Wish we had been able to stay longer. Shuttle into town was a huge advantage . It isn't free, however, because it is part of the resort fee as is the parking fee, which actually was more than advertised. Be sure to request a breakdown of the charges before checking out. When I received mine two days later by request, my card had been charged more than the statement came to!

The exterior of The Marker Resort is displayed, showcasing a two-story building featuring white horizontal siding and a large front porch with multiple seating areas. Lush green palm trees and tropical plants surround the entrance, while bright blue skies add a serene backdrop.