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.

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Guest favorite

Home in Key West

4.94 out of 5 average rating, 270 reviews

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.

Sep 21 – 28

G$104,849 GYD per night

Guest favorite

Condo in Key West

4.83 out of 5 average rating, 241 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

La Dolce Vita is a one bedroom, one bath condo with granite galley kitchen, living room, newer a/c, flooring, located in the heart of the Historic District in Old Town and is walking distance to all the shops, restaurants, bars and just steps to Duval Street! You will not need a car with this location. Large wraparound balcony with sitting chairs & table. Extra cleanings for an extra charge Southernmost Beach is just 3 short blocks away. Southernmost Point, Hemingway House, Butterfly World.

Sep 11 – 18

G$58,256 GYD per night

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Jul 4 – 11

G$45,387 GYD per night

Guest favorite

Townhouse in Key West

4.87 out of 5 average rating, 174 reviews

*Sparkling new kitchen* 3 bedroom/3 bath home.

Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and two queen beds. The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer installed. The salt water pool is perfect for lazing away your days. There is on street parking for two cars. The center of town is ten minutes away. An entire home for the price of one hotel room.

Sep 18 – 25

G$97,664 GYD per night

Superhost

Vacation home in Key West

4.88 out of 5 average rating, 226 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.

Mar 12 – 19

G$84,631 GYD per night

Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 525 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Jun 23 – 30

G$76,261 GYD per night

Guest favorite

Condo in Key West

4.89 out of 5 average rating, 142 reviews

Large waterfront 2/2 end unit with boat slip

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, tiki bar & grills, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Nov 16 – 23

G$149,139 GYD per night

Guest favorite

Townhouse in Key West

4.96 out of 5 average rating, 225 reviews

Stunning Townhouse * Full kitchen! * Sleeps 6

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 21/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all!

Feb 24 – Mar 3

G$181,153 GYD per night

Superhost

Townhouse in Key West

4.86 out of 5 average rating, 127 reviews

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and 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, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

Oct 8 – 15

G$58,765 GYD per night

Superhost

Apartment in Key West

4.89 out of 5 average rating, 897 reviews

At Mine | Key West Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Sep 13 – 20

G$57,116 GYD per night

Superhost

Apartment in Key West

4.92 out of 5 average rating, 165 reviews

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.*

Feb 28 – Mar 7

G$144,992 GYD per night

Guest favorite

Apartment in Key West

4.97 out of 5 average rating, 235 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).

Mar 30 – Apr 6

G$157,417 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Key West rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

Home in Cudjoe Key

4.88 out of 5 average rating, 188 reviews

Newly Renovated Oceanside House with Pool

Nov 14 – 21

G$85,710 GYD per night

Guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 119 reviews

Cudjoe Key Home with a View

Sep 19 – 26

G$61,067 GYD per night

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 117 reviews

Marathon one-level home on the Marina - with slip!

Aug 26 – Sep 2

G$133,688 GYD per night

Superhost

Home in Key Colony Beach

4.81 out of 5 average rating, 131 reviews

Waterview from three sides, Cabana Club, 30' Docks

Feb 17 – 24

G$81,372 GYD per night

Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 220 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

Nov 30 – Dec 7

G$83,963 GYD per night

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

Jan 28 – Feb 4

G$138,910 GYD per night

Guest favorite

Home in Key West

5.0 out of 5 average rating, 6 reviews

Key West Lighthouse Suite

Oct 27 – Nov 3

G$153,142 GYD per night

Superhost

Home in Upper Sugarloaf Key

4.87 out of 5 average rating, 45 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Feb 9 – 16

G$195,170 GYD per night

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Condo rentals with a pool

Guest favorite

Condo in Key Colony Beach

4.96 out of 5 average rating, 171 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Oct 24 – 31

G$71,379 GYD per night

Guest favorite

Condo in Key West

4.85 out of 5 average rating, 143 reviews

Anchor Drop modern elegance upgrades throughout vi

Nov 25 – Dec 2

G$175,016 GYD per night

Superhost

Condo in Key Colony Beach

4.8 out of 5 average rating, 105 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

Dec 20 – 27

G$63,894 GYD per night

Guest favorite

Condo in Marathon

4.87 out of 5 average rating, 190 reviews

Sombrero Beach Tropical Getaway

Jul 9 – 16

G$47,304 GYD per night

Guest favorite

Condo in Tavernier

4.88 out of 5 average rating, 227 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Jul 26 – Aug 2

G$58,059 GYD per night

Guest favorite

Condo in Tavernier

4.95 out of 5 average rating, 105 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Sep 4 – 11

G$54,543 GYD per night

Guest favorite

Condo in Key West

4.99 out of 5 average rating, 78 reviews

*Come to my Deck for a time you won't Forget!

Oct 24 – 31

G$94,405 GYD per night

Superhost

Condo in Key West

4.89 out of 5 average rating, 75 reviews

Ocean Front Studio private Sandy Beach in Key West

Mar 22 – 29

G$69,552 GYD per night

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Quick stats about vacation rentals with a pool in Key West

Total rentals	1.4K properties
Rentals with dedicated workspaces	710 properties have a dedicated workspace
Pet-friendly rentals	330 properties allow pets
Family-friendly rentals	930 properties are a good fit for families
Total number of reviews	34K reviews
Nightly prices starting at	G$18,807 GYD before taxes and fees

Vacation rentals with a pool in Key West

Top-rated rentals with a pool in Key West

Vacation rentals for every style

Cabins

Apartments

Houses

Popular amenities for Key West rentals with a pool

House rentals with a pool

Home in Cudjoe Key

Home in Cudjoe Key

Home in Marathon

Home in Key Colony Beach

Home in Cudjoe Key

Home in Marathon

Home in Key West

Home in Upper Sugarloaf Key

Condo rentals with a pool

Condo in Key Colony Beach

Condo in Key West

Condo in Key Colony Beach

Condo in Marathon

Condo in Tavernier

Condo in Tavernier

Condo in Key West

Condo in Key West

Quick stats about vacation rentals with a pool in Key West

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