
Holiday rentals with a pool in Cowpet Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cowpet Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Cowpet Bay rentals with a pool
House rentals with a pool

Heated Pool, OceanView, Generator, Local Discounts
Wonderful place to stay! It felt private and safe. It was a little challenging to get to, but as with anywhere on the island, without the adventure you don’t get the views! Stacie had exceptional communication, including a guide for nearby beaches/restaurants/grocery stores. Very clean. What stood out most were the “extra” amenities. We made use of the beach chairs, beach towels, a pair of snorkeling fins, etc., even the first aid kit! Would highly recommend!

Condo by the beach! ¡Condo a pasos de la playa!
An extra-spacious accommodation in an incredible location at good value. We hope to return soon!

3 bedroom Villa Great End Location
Check in was easy and the Mgr Jerscilla provided recommendations with airport transfers, jeep rental, and excursions. She greeted us and walked us through the layout and use of modern electronics of the villa. It was stocked with snacks, coffee, water, paper towels, seasoning, and basic condiments that were very appreciated. Those items add up when you need to buy a few things from local grocery stores. The villa set up has the courtyard in the center with pool, games, outdoor dining, outdoor bar, TV lounge area, and Sonos speakers. I have these at my home. Kitchen, dining and living on one side with bedrooms and bathrooms on the other. We really liked the bidets and quality TP! A perfect set up for privacy that was gated. We will go back and will stay here again if it’s available.

Seaside Charm - Beachfront Romantic Getaway!
We really enjoyed Julies dwelling. It was in an area that was laid back and comfortable but had all the amenities needed in walking distance. The beach front was amazing with its clear clean water and access to two reefs that provided fantastic snorkeling. Coffee shop, bar, restaurants were just a short walk away. Julie was very flexible with us and was very very responsive to any of our questions.

Villa Fratelli Giardino
Our stay at this property was excellent. The views were remarkable, the house was well-equipped (including a generator), and the location was convenient to Red Hook and the East End. Groceries, pharmacies, restaurants, and shopping were easily accessible. The photographs accurately depicted the premises. Host Randall and his staff were very responsive and helpful. We enjoyed our week here and hope to stay at this home again.

Caribbean Poolside Cottage
Michael and Jenny were above and beyond the best hosts we have had from AirBnB. From the beautiful location, amazing recommendations, and easy going demeanor you couldn’t ask for more. Everything about the description is accurate and you can expect the view to be even better in person. They also provided a detailed cottage guide that clearly stated guest expectations and provided amazing recommendations for beaches/restaurants/groceries/etc.

Caribbean Cottage Near the Sea
My husband and I spent our honeymoon at St. John and choosing Ramona and Chris’s place was absolutely perfect. Chris met us when we got our rental car and led us to the Airbnb which was so kind and helpful. He gave us a ton of local recommendations and answered any questions we had throughout the week. The views are absolutely breathtaking and are hard to fully capture on their listing pictures! The AC worked wonderfully and the outdoor shower made things feel extra tropical! The place came with a few cat friends that we thoroughly enjoyed and the stairs were the perfect workout in the morning before the beach. We hope to come back to St. John in the near future and will most definitely be back here if it is just the two of us! Thanks for making our trip so memorable with a wonderful home for the week!!

Island Daze - Amazing Views
This is a beautiful retreat - the views, the condo, all refreshing and relaxing. We booked at the last minute and thoroughly enjoyed the space. Highly recommend an SUV/Jeep and be mindful they drive on the left! Condo is located at the top of the resort where the parking lot is located a short walk up a hill, not near the condo. We drove down to condo to unload in the small circle and managed to turn around without incident. The condo is located down 3 short flights of stairs. The condo buildings and grounds look tired, railings are loose. Once inside condo, you will be mesmerized by how nice and comfortable it feels - bed and pillows are very comfortable. Kitchen has everything you'll need - we shopped at both The Market at Tutu Mall and Moes in Red Hook for food - Moes is much nicer, everywhere is expensive! We drove down to the pool closest to the ocean, very clean. We did not go to restaurant. Coki Beach is within a walk but we found it extremely crowded and trash everywhere.
Apartment rentals with a pool

Sueño del Mar 2 BDRM at Cowpet Bay East
From start to finish, great experience! Staisha answered the phone on the 1st day when I was on the wrong street. Amy answered me every time I messaged her with a question. Both were prompt & courteous. The condo is absolutely beautiful & met all of our needs and desires. We had a fantastic stay and highly recommend Amy!!! Thank you!

Sapphire Village Off Season Discounts (See Below)
The place was as described, close to Red Hook and very short walk to Sapphire Beach! Had two swimming pools available to use, grills to cook on, etc. Sue was very helpful and responsive, would definitely stay at her place again!

Seen on HGTV- Sapphire direct beachfront penthouse
Such a beautiful condo with outstanding views. Lidiya had all kinds of beach amenities which came in so useful for my husband and I. The location was absolutely perfect, and we did not have the want to leave the premises with everything this location had to offer. We can not wait to return! Thank you again, Lidiya for allowing us to stay in your home! We had the time of our lives!

HarborHouse-PRIME OCEANFRONT VILLA SAPPHIRE BEACH
Ben and Erica were great hosts. They answered our questions promptly. The location was perfect, and the condo was as described. Would recommend Ben and Erica’s place and plan to return.

Entire 1st Floor 2BR Beachfront Elysian Resort
Just had a wonderful stay with my family of four here. Highly recommend! It was spacious, clean, nicely appointed (especially the kitchen). We enjoyed the quiet beach, pool, and both onsite restaurants. Great location with a short drive into Red Hook and other beaches. Would stay again!

Villa in Paradise with Private Pool and Generator
LISTEN TO YOUR HOST! Laverne strongly recommended we get a rental car — my wife and I love to walk so we didn’t get one — we will not go back to St. Thomas unless we rent a car! Now the space: the pictures don’t do it justice the bedroom, pool area, bathroom, and living room are larger than perceived in photos and the kitchen has ample room for one cook at a time, two if you’re skilled! All areas of the accommodation were spotless and insectless inside! The bed is better than ours at home and we’re still thinking about that one of a kind bathroom and the pool lights! I swear the walls are sound proof, there were families in either side of us with kids and we never heard a peep inside. The property grounds and walkways are well maintained Laverne is a master of instructions. We never had to double text, ask what was meant, clarify our end, it was smoother than we had even hoped and for that we would recommend this place to anyone, especially for their honeymoon like we did!

Luxury 1/1 Oceanfront @ Sapphire Beach Resort
Ana's condo was great. We LOVED the location and Ana was very responsive. We will be back!

Salt Life at Sapphire Beach
Great place to stay! Very convenient if you want to explore St. John too! John was responsive and kind. We really appreciated the recommendations and insights into the area prior to our stay. We would love to stay here again soon!
Destinations to explore
- Carolina Holiday rentals
- Culebra Holiday rentals
- Saint Thomas Holiday rentals
- Saint Croix Holiday rentals
- Tortola Holiday rentals
- Luquillo Holiday rentals
- Fajardo Holiday rentals
- Palmas del Mar Holiday rentals
- Vieques Holiday rentals
- Condado Beach Holiday rentals
- San Juan Holiday rentals
- Punta Cana Holiday rentals
- Waterfront rentals Cowpet Bay
- Villa rentals Cowpet Bay
- Rentals with a patio Cowpet Bay
- Beachfront rentals Cowpet Bay
- Family-friendly rentals Cowpet Bay
- Rentals with a kayak Cowpet Bay
- Apartment rentals Cowpet Bay
- Rentals with a firepit Cowpet Bay
- House rentals Cowpet Bay
- Rentals with a hot tub Cowpet Bay
- Rentals with beach access Cowpet Bay
- Family-friendly rentals Cowpet Bay
- Rentals with an EV charger Cowpet Bay
- Rentals with a washing machine and dryer Cowpet Bay
- Hotel rentals Cowpet Bay
- Flat rentals Cowpet Bay
- Resort rentals Cowpet Bay
- Rentals with outdoor seating Cowpet Bay
- Fitness-friendly rentals Cowpet Bay
- Rentals with pools East End Region
- Rentals with pools U.S. Virgin Islands
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Flamenco Beach
- Honeymoon Beach
- Magens Bay Beach
- Limetree Beach
- Mosquito Bay Beach
- Oppenheimer Beach
- Coki Beach
- Cane Garden Beach
- Chocolate Hole
- Cinnamon Bay Beach
- Cane Bay Beach
- Peter Bay Beach
- Gibney Beach
- Pelican Cove Beach
- Josiah's Bay
- Playa Sun Bay
- Caneel Bay Beach
- Maho Bay Beach
- Salt River Beach
- Virgin Islands National Park
- Oil Nut Bay
- Grapetree Beach
- Hull Bay Beach
- Secret Harbor Beach