
Vacation rentals with a pool in Key West
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Key West
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Sea Ray Cove; Pool, 75’ Dock and steps to Beach
2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

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.

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.

Gorgeous Ocean View in Paradise, Close to Key West
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

Oceanfront Breeze, Stunning Views, Beach/Pool
Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Tropical Old Town Bungalow
Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage
Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

Anglers Terrace, Condé Nast Traveler's Best Airbnb
As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

Poolside Cottage #411
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Duval St Apartment w/ Balcony w/parking Adult Only
This large apartment overlooks Duval Street from a private balcony. Perfect location in the heart of Old Town within easy walking distance of restaurants, live music, and historic sites. Guests enjoy daily complimentary continental breakfast in the garden and dips in our heated pool. *Please note you must be 21 or older to make a reservation on this property and all guests must be at least 18 years old.*

Duval Street Suites with full kitchen heated pool,
Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duval street in historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.
Popular amenities for Key West rentals with a pool
House rentals with a pool

Easy Livin' by AvantStay | Mins to the Ocean!

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

Cudjoe Key Home with a View

Oceanfront with Pool near Sombrero Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Beach House, Private Pool & Dock, Gulf Sunset view

Grand Blue/Dock/HtdPool/TropicalSandPatio/GameRoom

Oct. & Nov. 50% off! Oceanfront, 4 Bikes 2 Kayaks
Condo rentals with a pool

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Canal View Condo w/ Pool, Balcony & Bar

Tropical Escape at Sunrise

Anchor Drop modern elegance upgrades throughout vi

Fair Winds @ The Foundry~ Frolic On Duval St

Private Beach in Marathons Key Colony Beach

EYW Getaway

Hyatt Beach House-Quiet Key West Spot!
Other vacation rentals with a pool

The Barnacle at Venture Out - Waterfront with Dock

Poolside Cottage at Simonton Court - Adults Only

Key West Condo 2B/2B with Pool & Boat FREE Slip

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Rise And Shine On The Water

Downtown KeyWest 2Bed Oceanfront

Private Pool! Luxury Paradise Pointe, Pet Friendly
Quick stats about vacation rentals with a pool in Key West
Total rentals
1.7K properties
Nightly prices starting at
€ 9 before taxes and fees
Total number of reviews
42K reviews
Family-friendly rentals
1.1K properties are a good fit for families
Pet-friendly rentals
510 properties allow pets
Rentals with dedicated workspaces
840 properties have a dedicated workspace
Destinations to explore
- Seminole Vacation rentals
- Miami Vacation rentals
- Central Florida Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Four Corners Vacation rentals
- Tampa Bay Vacation rentals
- Rentals with a fire pit Key West
- Rentals with a washer and dryer Key West
- House rentals Key West
- Beachfront rentals Key West
- Rentals with a fireplace Key West
- Fitness-friendly rentals Key West
- Apartment rentals Key West
- Hotel rentals Key West
- Cottage rentals Key West
- Townhouse rentals Key West
- Serviced apartment rentals Key West
- Villa rentals Key West
- Rentals with an accessible height toilet Key West
- Rentals with breakfast Key West
- Rentals with lake access Key West
- Waterfront rentals Key West
- Rentals with a hot tub Key West
- Beach house rentals Key West
- Rentals with beach access Key West
- Condo rentals Key West
- Rentals with outdoor seating Key West
- Rentals with a kayak Key West
- Rentals with an EV charger Key West
- Boat rentals Key West
- Luxury rentals Key West
- Pet-friendly rentals Key West
- Boutique hotel rentals Key West
- Mansion rentals Key West
- Family-friendly rentals Key West
- Smoking-friendly rentals Key West
- Rentals with a patio Key West
- Bed and breakfasts Key West
- Rentals with pools Monroe County
- Rentals with pools Florida
- Rentals with pools United States
- Things to do Key West
- Tours Key West
- Sports activities Key West
- Food and drink Key West
- Sightseeing Key West
- Art and culture Key West
- Nature and outdoors Key West
- Things to do Monroe County
- Nature and outdoors Monroe County
- Food and drink Monroe County
- Art and culture Monroe County
- Entertainment Monroe County
- Sightseeing Monroe County
- Sports activities Monroe County
- Tours Monroe County
- Things to do Florida
- Sightseeing Florida
- Wellness Florida
- Tours Florida
- Art and culture Florida
- Nature and outdoors Florida
- Entertainment Florida
- Food and drink Florida
- Sports activities Florida
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Wellness United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States