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Vacation 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.

Guest favorite
Home in San Cayetano de Venecia, Costa Rica
Quinta La Ceiba Modern Home with Pool in DairyFarm
A contemporary roomy vacation home situated in a dairy farm. Embrace serenity, unwind in a tranquil haven surrounded by cows grazing in lush green fields. It's a birdwatcher's paradise too. This is an ideal escape to disconnect and reconnect with nature. Dine and lounge outdoors make the most of the property's features. Our in-house travel concierge will be glad to arrange tours and activities for you at no additional cost. Consider our private chef service for an even more memorable experience.
Jan 27 – Feb 3
$170 per night
4.95 out of 5 average rating, 128 reviews
Guest favorite
Condo in Miami, Florida
ICON 2B/2B Skyline Free Pool, Spa, HotTub
INSTA READY, This unit provides over 1,350SqFt of breathtaking ocean and city views with Two Bedrooms and Two Bathrooms. Located within the luxurious Icon building. The Icon is a 5 star condominium. It is located inside the heart of Downtown Miami/ Brickell. It includes the same amenities as the W Hotel, such as free access to spa, pool, hot tub, and 4 restaurants, including Cipriani. The apartment comes with three flat screen TVs, HighSpeed WiFi, and toiletries. As well as four separate beds.
Jul 27 – Aug 3
$328 per night
4.9 out of 5 average rating, 138 reviews
Guest favorite
Condo in Montego Bay, Jamaica
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
This new beach theme apartment is located in 22 Freeport – A gated community in Freeport Montego Bay. 22 Freeport is a beach front complex on a Marina that features 24 hour security, a gym, infinity edge pool and playground; whilst the unit on the ground floor opens onto a cozy back yard space that flows into an open green space. Be sure to check out my other units in this community on my profile if your dates are not available or if you would like to book them all for your large group.
Oct 5 – 12
$195 per night
4.92 out of 5 average rating, 360 reviews

Popular amenities for Caribbean rentals with a pool

House rentals with a pool

Guest favorite
Home in Hollywood, Florida
Pool House 3B/2B King Bed EV-Charger Hollywood, FL
Sep 21 – 28
$374 per night
4.86 out of 5 average rating, 153 reviews
Guest favorite
Home in Naples, Florida
Island lifestyle family vacation home (Salt Pool)
Jan 23 – 30
$372 per night
4.98 out of 5 average rating, 200 reviews
Guest favorite
Home in Fort Lauderdale, Florida
Beach area chic cabana home/pool/BBQ
Jun 29 – Jul 6
$295 per night
4.99 out of 5 average rating, 152 reviews
Guest favorite
Home in Rincon, Puerto Rico
Casa Ensenada- Rincon Puerto Rico
Sep 22 – 29
$413 per night
4.91 out of 5 average rating, 200 reviews
Superhost
Home in Fort Lauderdale, Florida
Bamboo House/step 2 beach/Heated Pool/Spa
Aug 24 – 31
$469 per night
4.96 out of 5 average rating, 125 reviews
Guest favorite
Home in Adjuntas, Puerto Rico
Secluded Coffee Farm House w/Chimney & Heated Pool
Oct 25 – Nov 1
$568 per night
4.97 out of 5 average rating, 179 reviews
Guest favorite
Home in Lake Worth, Florida
Tropical Beach Villa with Heated Salt Water Pool
Jan 11 – 18
$610 per night
4.97 out of 5 average rating, 148 reviews
Guest favorite
Home in Stake Bay, Cayman Islands
Modern Oceanfront, 2Primary Suites, sleeps 6, pool
Oct 31 – Nov 7
$411 per night
5.0 out of 5 average rating, 33 reviews
Guest favorite
Home in Gros Islet, St. Lucia
Gorgeous 3BR2BA Oceanfront Villa w/Pool, Concierge
Oct 25 – Nov 1
$974 per night
4.98 out of 5 average rating, 66 reviews
Guest favorite
Home in Lake Worth, Florida
Modern beach escape with heated pool
Dec 20 – 27
$174 per night
4.93 out of 5 average rating, 72 reviews
Guest favorite
Home in Vieques, Puerto Rico
Casa Cumbre - Spectacular views, location and pool
Oct 5 – 12
$600 per night
5.0 out of 5 average rating, 33 reviews
Guest favorite
Home in Northside, U.S. Virgin Islands
La Luz
Aug 31 – Sep 7
$997 per night
4.89 out of 5 average rating, 9 reviews

Condo rentals with a pool

Guest favorite
Condo in Carolina, Puerto Rico
Beach Front Condo with Endless Ocean Views
Aug 15 – 22
$350 per night
4.99 out of 5 average rating, 134 reviews
Superhost
Condo in Miami, Florida
Waterfront Spacious Luxury 1 Bedroom IconBrickell
Oct 19 – 26
$175 per night
4.79 out of 5 average rating, 151 reviews
Superhost
Condo in Miami, Florida
Large Designer Condo, Unique Ocean Views, SmartTVs
Oct 23 – 30
$570 per night
4.88 out of 5 average rating, 123 reviews
Superhost
Condo in Carolina, Puerto Rico
Breathtaking Views, Beachfront, Remodeled!
Aug 13 – 20
$454 per night
4.92 out of 5 average rating, 177 reviews
Guest favorite
Condo in Tower Isle, Jamaica
2 bedroom Oceanfront condo with a pool
Oct 11 – 18
$192 per night
4.88 out of 5 average rating, 125 reviews
Guest favorite
Condo in Kingston, Jamaica
Stunning smart apt with pool & amazing sunset view
Sep 28 – Oct 5
$90 per night
4.92 out of 5 average rating, 166 reviews
Guest favorite
Condo in Kingston, Jamaica
Entire Luxury Uptown Penthouse 3Bedroom/3baths
Nov 8 – 15
$233 per night
4.88 out of 5 average rating, 110 reviews
Guest favorite
Condo in Cartagena, Colombia
Beachfront Apartment with best location and view
Aug 31 – Sep 7
$95 per night
4.92 out of 5 average rating, 156 reviews
Superhost
Condo in Santo Domingo, Dominican Republic
Welcoming Studio Surrounded by Beautiful Garden
May 2 – 9
$66 per night
4.89 out of 5 average rating, 532 reviews
Guest favorite
Condo in Punta Cana, Dominican Republic
Serena Village Paradise
Nov 2 – 9
$42 per night
4.81 out of 5 average rating, 348 reviews
Guest favorite
Condo in Cartagena, Colombia
New apartment overlooking the private sea-Jacuzzi
Aug 2 – 9
$69 per night
4.91 out of 5 average rating, 248 reviews
Guest favorite
Condo in Kingston, Jamaica
★Light &Bright 1-bedroom apartment w pool & grill
Jun 4 – 11
$111 per night
4.96 out of 5 average rating, 114 reviews

Home rentals with a private pool

Guest favorite
Cottage in La Romana, Dominican Republic
Chic Cottage Nature Casa de Campo
Oct 22 – 29
$300 per night
5.0 out of 5 average rating, 138 reviews
Guest favorite
Townhouse in Cartagena, Colombia
Luxurious Townhouse With Private Pool in The Old City
Jul 12 – 19
$588 per night
4.86 out of 5 average rating, 170 reviews
Guest favorite
Home in Santo Domingo, Dominican Republic
Gorgeous Colonial House near Cafes and Bars
Nov 3 – 10
$144 per night
4.95 out of 5 average rating, 335 reviews
Guest favorite
Apartment in Cartagena, Colombia
Old City Luxury Villa - Staff & Breakfast Included
Sep 16 – 23
$728 per night
4.86 out of 5 average rating, 131 reviews
Guest favorite
Loft in Rincon, Puerto Rico
Walk to Sandy Beach from a Hilltop Villa with a Pool
May 2 – 9
$168 per night
4.98 out of 5 average rating, 248 reviews
Guest favorite
Guesthouse in West Palm Beach, Florida
Tropical Cabana with Pool in West Palm Beach
Oct 16 – 23
$200 per night
4.99 out of 5 average rating, 149 reviews
Guest favorite
Home in West Palm Beach, Florida
Soak up the Beachy Vibe at a Vibrant Poolside Paradise
Jul 31 – Aug 7
$300 per night
4.95 out of 5 average rating, 142 reviews
Guest favorite
Condo in San Juan, Puerto Rico
Condado Beach Vistas by Cesar 2501
May 19 – 26
$182 per night
4.9 out of 5 average rating, 196 reviews
Guest favorite
Villa in Santo Domingo, Dominican Republic
Casa Pantheon Luxury Colonial House
Sep 21 – 28
$396 per night
4.92 out of 5 average rating, 275 reviews
Superhost
Apartment in Puerto Plata, Dominican Republic
Beachfront Condo With Private Pool, Patio & Resort Access
Jan 17 – 24
$214 per night
4.76 out of 5 average rating, 92 reviews
Guest favorite
Villa in Holetown, Barbados
Walk to the Beach From a Poolside Retreat in Sunset Crest
Oct 15 – 22
$304 per night
4.94 out of 5 average rating, 72 reviews
Superhost
Home in Fort Lauderdale, Florida
Mid Century Modern Pool Home In the Best Location!
Oct 8 – 15
$230 per night
4.63 out of 5 average rating, 32 reviews

Destinations to explore