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Holiday rentals with a pool in Caribbean

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Caribbean

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Home in Plantation

4.68 out of 5 average rating, 73 reviews

PRIVATE POOL-Paradise Home-Fort Lauderdale

Beautiful Cozy Completely renovated House featuring 4 bedrooms, all the rooms with smart TV and Memory Foam Mattress, 2 full baths with Shower Panel Tower. Arcade machine and Foosball to make your stay more fun. Beautiful open kitchen with stainless steel appliances, with everything you need to feel at home. Close Gate, fits RV, boat, and trailer. Large backyard with an amazing pool, outdoor furniture, BBQ, hammock, and fire pit. Come build a lifetime of memories with family and friends.

Home in Fort Lauderdale

4.75 out of 5 average rating, 48 reviews

Fresh Pool Home! Managed by BNR Vacation Rentals

Introducing our brand new 3-bedroom vacation home, offering a fresh and clean ambiance for your getaway. The pool, shared with just one other identical unit, offers a refreshing escape on warm days, while the private backyard provides a serene space to unwind and relax. This cozy retreat ensures a comfortable stay with its modern amenities and inviting atmosphere. Equipped with smart TVs and cable in both the master and living room, you can enjoy your favorite shows and movies during your stay.

Guest favourite

Condo in East End

4.9 out of 5 average rating, 207 reviews

Luxury Beachside Escape with private pool and wifi

This villa was just renovated and is absolutely amazing, plus no one can see you in our private pool or patio. Stunning views of the pool and palm trees throughout the villa. New kitchen and bathroom with luxury finishes, this beachside escape is a short walk to Sapphire beach and Lindquist beach which are two of the best beaches in the Caribbean. New king mattress, new 55" TV, Cable, DVDs, great furniture, amazing shower with garden and so much more. We promise you will absolutely love it!

Guest favourite

Villa in Pembroke Pines

4.88 out of 5 average rating, 219 reviews

Stunning Lake-Front Villa with Pool & Spa

This beautifully renovated and spacious villa is the perfect spot for your South Florida getaway! Located in the family-friendly neighborhood of Pembroke Pines, this home boasts a large heated swimming pool and spa, furnished deck and stunning lake-front views. The interior features 2 large living rooms, 2 dining areas, a state-of-the-art kitchen, 5 comfortable bedrooms and 2 modern bathrooms. Also included are free parking, laundry room, gaming tables, 6 TVs, BBQ grill and high-speed wifi.

Guest favourite

Home in Davie

5 out of 5 average rating, 108 reviews

Modern pool home on lake near Hardrock FLL airport

Luxurious lakefront pool home, newly remodeled modern design, conveniently located within minutes of Hardrock Hotel & Casino and Ftl airport. Spacious enough for the whole family. Private and quiet. Sit by the pool and watch the beautiful Florida sunsets or head east 15 minutes to the famous Ft. Lauderdale beach. Enjoy the firepit, light up the BBQ, and enjoy the day poolside. Publix is located less than 1 minute away. Looking for a rental car for your trip? Message me today for more info!

Guest favourite

Home in Fort Lauderdale

4.87 out of 5 average rating, 183 reviews

Stunning gardens! Spa and heated pool

Highlights of this upgraded house include: high end outdoor bar and kitchen; spectacular outdoor garden areas, multiple sun decks, screened in outdoor living room with TV & crate and barrel furniture; heated saltwater pool and spa. Inside you’ll find a beautiful, fully stocked kitchen, primary bedroom with en suite, polished concrete floors, beach towels /beach chairs, soaps, coffee/teas; 8 minutes to the beach, restaurants, downtown Fort Lauderdale; nothing is shared - A private oasis!

Guest favourite

Villa in Playa Hermosa

4.94 out of 5 average rating, 66 reviews

Tropical Beach Villa with Pool

Relax in a private Villa within a complete resort. Private secluded plunge and lap pool in the patio. The resort has 2 large shared pools with swim up bar/ children’s pool and a hot pool. Nightly entertainment and weekend music. Restaurant/ mini market and pizza cafe. Concierge desk and property manager on site A shuttle bus runs every 15 mins to take you/ from to the nearby beach . Very good beachfront restaurants are within a short walk. Hermosa beach is a flat , warm blue flag .Wow

Guest favourite

Home in Venice

4.91 out of 5 average rating, 181 reviews

Vacation Rental with private swimming pool

Located in a desirable community of South Venice. Venice, Manasota, Nokomis and Sharky’s beaches are located only 5 miles away. The historic Venice Avenue of unique shops, restaurants, special events. Farmer market, tennis courts, and children fountain are close by. Newly renovated home and swimming pool in a quiet peaceful area in an ideal place for any season gateway.A great place for biking, running and walking. My place great for couples, solo adventurers or families with kids.

Guest favourite

Home in North Port

4.96 out of 5 average rating, 114 reviews

Private, beautiful house with a heated pool

Relax with the whole family or a group of friends at this peaceful place in paradise. A beautiful, clean home that can accommodate up to 6 guests. The home is fully remodeled with new furniture. Start your morning with a nice cup of Nespresso by the heated pool and end the night at the jacuzzi in the spacious master bedroom. Located 5 min away from water park(aquatic center) 10 min from the famous Warm Mineral Springs and 25 min from multiple beaches.

Guest favourite

Home in West Palm Beach

4.97 out of 5 average rating, 31 reviews

Amazing pool home

Welcome to our stunning 4/2 home just minutes from downtown West Palm Beach. Our heated pool & backyard oasis will make your visit memorable. Situated in a vibrant neighborhood, our home boasts convenience and comfort. With plenty of restaurants nearby, you'll have no shortage of dining options. Plus, being minutes from the outlet mall, beaches, Kravis ctr, and downtown, you will have endless entertainment options.

Guest favourite

Villa in Fort Lauderdale

4.99 out of 5 average rating, 127 reviews

Luxe 4BR Waterfront w/Htd Pool, 5min to beach

Luxurious private waterfront home minutes to gorgeous South Florida beaches, great restaurants, and much more! The home features luxury living at its finest with an open concept design, a gourmet kitchen, 4 generous bedrooms, 3 lavish bathrooms, a game room and a stunning resort yard with a kids playground, an outdoor kitchen/bar & a pool overlooking the canal.

Guest favourite

Home in Cape Coral

4.89 out of 5 average rating, 216 reviews

Modern Oasis pool paradise

Location! Location! The entire place. This is a brand new Condo with gorgeous pool located next to supermarkets, restaurants including famous seafood restaurant, very close to Captiva, Fort Myers and Sanibel beaches Beautiful modern decor quiet secluded amazing!!! Great pool. No pets no service dogs no comfort pets allowed owner is allergic.

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Popular amenities for Caribbean rentals with a pool

Free parking on premises

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House rentals with a pool

Guest favourite

Home in Hollywood

4.79 out of 5 average rating, 122 reviews

Amazin spacious 4/2 Pool Home in Hollywood FLL-MIA

Home in Noord

4.81 out of 5 average rating, 32 reviews

luxurious house private pool in tierra del sol Re

Home in Las Lomas #2

4.87 out of 5 average rating, 188 reviews

Nature Getaway Resort with private pool

Guest favourite

Home in Lauderhill

4.92 out of 5 average rating, 50 reviews

KING SUITE | BlG PRlVATE Backyard w. Pool | 2 LVRM

Home in Fort Lauderdale

4.84 out of 5 average rating, 152 reviews

Large Waterfront House with Pool 4bd/2ba

Home in Marco Island

4.54 out of 5 average rating, 13 reviews

Pet-friendly home w/ pool & steps to beach/food

Home in Sosúa

5 out of 5 average rating, 3 reviews

2 bdr. house with private pool Villa 704

Guest favourite

Home in Delray Beach

4.83 out of 5 average rating, 134 reviews

LUXURY!i - Heated Pool - Perfect Vacation

Condo rentals with a pool

Guest favourite

Condo in Fort Pierce

4.93 out of 5 average rating, 107 reviews

Modern BEACH Condo in Peaceful Hutchinson Island

Guest favourite

Condo in Naples

4.93 out of 5 average rating, 152 reviews

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

Guest favourite

Condo in Rockley

4.91 out of 5 average rating, 140 reviews

Spacious 2 Bedroom Luxury Condo.

Guest favourite

Condo in PR

4.83 out of 5 average rating, 170 reviews

Perfect Location 3bd2ba CondoVacation/Business

Condo in Pompano Beach

4.84 out of 5 average rating, 267 reviews

ON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b

Guest favourite

Condo in Sarasota

4.97 out of 5 average rating, 61 reviews

Peaceful retreat, pool, hot tub, near Siesta Key!

Condo in Northside

4.75 out of 5 average rating, 100 reviews

Lovely condo with two pools

Guest favourite

Condo in Bonita Springs

4.92 out of 5 average rating, 105 reviews

Amazing Condo-1 mile from Bonita Beach

Home rentals with a private pool

Guest favourite

Home in Santo Domingo

4.94 out of 5 average rating, 387 reviews

Gorgeous Colonial House near Cafes and Bars

Guest favourite

Home in West Palm Beach

4.95 out of 5 average rating, 155 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

Guest favourite

Villa in Santo Domingo

4.93 out of 5 average rating, 318 reviews

Casa Pantheon Luxury Colonial House

Guest favourite

Villa in Cartagena

4.87 out of 5 average rating, 144 reviews

Old City Villa - Breakfast & Housekeeping Included

Bungalow in Punta Cana

4.79 out of 5 average rating, 306 reviews

Sink into the Pool of a Wonderful Bungalow

Guest favourite

Townhouse in Cartagena

4.86 out of 5 average rating, 198 reviews

Luxurious Townhouse With Private Pool in The Old City

Guest favourite

Villa in Tamarindo

4.96 out of 5 average rating, 25 reviews

Tropical Retreat - Private Pool, Steps to Beach

Guest favourite

Condo in San Juan

4.91 out of 5 average rating, 245 reviews

Condado Beach Vistas by Cesar 2501

Destinations to explore