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

Cold? Book Now! Caribbean Sunshine! Amazing Views!
Book Now! Down Island Dream is a 1BR/1BA luxury villa @Point Pleasant Villas on the East End of St Thomas. 2 Restaurants, 3 pools, nature trail & a small intimate beach to enjoy. Your vacation home/5 minutes to Red Hook w/shops, bars, restaurants & the ferry to St John where you can explore, hike & enjoy our National Park Beaches! 3 mins to Lindquist & Coki beaches. Amazing views & refreshing breezes await you at Down Island Dream! Try our home away from home for the week & fall in love!

BEST REVIEWS on the East End - HANDS DOWN!
ALWAYS BOOK with an ON-SITE LOCAL to get the INSIDE SCOOP. Book this condo to gain access to custom-made handouts to help you plan a memorable vacation! You'll love the KILLER VIEW of the Caribbean Sea about 200 feet away. This condo includes toys and games, and plenty of beach toys, noodles, and extra chairs for beach hopping! I'm frequently booked, so check out my other condos in Cowpet Bay West. airbnb.com/h/stthomasparadise10 airbnb.com/h/stthomasparadise26 airbnb.com/h/stthomasparadise42

Hillside Hideaway
Perfect getaway for an island getaway, business, or solo adventuring. This well appointed one bedroom apartment is nestled in a quiet central hillside neighborhood with views of Hans Lollik, Jost Van Dyke, and Tortola islands. Conveniently located one mile from Magen's Bay and ten minutes to downtown Charlotte Amalie by car. Rental car is a must! Come enjoy the tranquil views, take a dip in the pool, and experience St. Thomas like a local. Please read all listing details and house rules.

Honeymoon-Worthy w/ Pvt Pool Walk 2 Sapphire Beach
We fell in love with the island of perpetual summer. There's something special about having your own villa w/ a private pool. We also love the garden shower & the location. Pangea, the restaurant on site is phenomenal. The property is so close to our fave spots. Beautiful Sapphire Beach is in walking distance via a gate at the south end of the property. It boasts the Beach Buzz coffee & bfast spot, a Beach bar & grill w/ live music weekly, Paradise Pie pizza & SeaSalt fine dining restaurants.

Wrap Around Balcony~Views~Pack your Bathing Suit!
What a Vacation Home! Amazing Views! Freshly Remodeled! Welcome to C'est Jolie, newly decorated hilltop corner unit featuring breathtaking views of St. John, Tortola & Jost Van Dyke. 1BR/1BA vacation home is yours for however long you book - each time you walk in the view will take your breath away! Brand new furniture, fresh paint, 2 ACs, 2 TVs will have you on island time in no time. Perfect East End location next to Margaritaville 2 minutes to Coki Beach, 3 minutes to Lindquist Beach.

Sunrise Cottage - Secluded, Romantic, Private
Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Ocean View Condo near Magen’s Bay - Pool/Generator
Welcome to your retreat with panoramic ocean views located in Mahogany Run, 5 mins from Magen's Bay Beach. Enjoy spectacular views of the ocean from every room of the condo. This bright and airy condo is equipped with a plush king-size bed, a fully equipped kitchen, and a bathroom featuring a walk-in shower. Spend the days at one of the island's beaches, snorkeling, hanging out by the pool, or exploring downtown Charlotte Amalie! We HIGHLY recommend renting a car to get around the island

Million Dollar Views: 2 mins to Beach, Pool, more
One of the BEST places in St Thomas, with a gorgeous kitchen, bathroom, comfortable king bed and teak furniture. This villa is 20 feet over the water, so you see fish swim by and enjoy sounds of the waves below. High end sheets, towels, beach towels, beach chairs, snorkel gear, soap, shampoo, conditioner, plus a new 55" TV and high-speed WiFi. 3 pools and 2 restaurants on property, plus I provide details on all the best beaches, restaurants, bars, stores and more. You will LOVE it!

Private Pool in Paradise! Ocean View Steps 2 Beach
Come enjoy the island life at this tranquil villa with private pool...only steps from the beach! Cooler, snorkeling gear, and beach chairs INCLUDED! The entire home has been remodeled. The pool has been fully updated as well as the deck area, which includes brand new furniture and high-end loungers. A new gas grill has also been added for your outdoor grilling pleasure. Stream all your favorites with our strong Wi-Fi. Upscale restaurant, Pangea, is just steps away. Free parking.

Oceanfront Bliss & Perfect Sunsets + Backup Power
Our fully renovated 1BR/1BA condo is PERFECT for couples, small families or a friends getaway. Enjoy stunning ocean views and the sound of waves from every room or your private balcony. Watch breathtaking sunsets and cool off in one of three crystal-clear pools. Located in a gated community, just steps from the beach, oceanside pool, and seaside dining. Only 10 min to Red Hook (ferries to St. John & BVI) and Havensight, and 15 min from the airport—your perfect island escape! 🌴

Chic 1 Bedroom Oasis with Designer Decor & Pool
Welcome to our impeccably designed oversized 1-bedroom apartment (+ queen size Murphy bed) a stylish retreat that promises an unforgettable stay in the heart of the historic district of Charlotte Amalie with its own plunge pool and deck. This apartment boasts a sophisticated ambiance, curated with the finest designer furnishings, decor and lighting as well as a custom kitchen. This is a perfect location to serve as the base to explore St. Thomas and the surrounding islands.

Sunshine Daydream - Our little piece of paradise!
Spend your days between at Sunshine Daydream with its beautiful ocean views. Rise up to paradise enjoying the gorgeous sunrises and sunsets from the private rooftop deck. This rental offers a fully equipped kitchen, 3 different pools, one of which is steps from the condo. There is easy beach access and we are centrally located between Charlotte Amalie and Red Hook. To top it off there are 2 restaurants and a bar within walking distance from the unit.
Popular amenities for Saint Thomas rentals with a pool
House rentals with a pool

Island Retreat - Generator/Ocean View/Heated Pool

Seaside Lux: Steps to the sand a true oasis!

Secluded Villa with Ocean Views

The Caribbean Farmhouse/Ocean Views, Solar Power

Caribbean Poolside Cottage

Waterfront Villa Tryst on Hull Bay (3 bedrooms)

Private Pickleball Court - 5 min walk to Beach

Beautiful 3 Bedroom w/Saltwater Pool & Great Views
Apartment rentals with a pool

Rockroom One Bedroom Condo at The Hills Saint John

Serene Beach Condo | Sapphire | 1BR | 2 Pools

Stunning Ocean View w/Balcony~Shades of Sapphire~

Two Bedroom Beachfront Condo at Sapphire Beach

Sea-N-Dipity 1 by the Sea @ Sapphire Resort

Sea Dreams at Regatta Point Villas

Romantic Private Pool Villa@Sapphire. Generator.

Sail Away II-WOW Beachfront to Paradise Remodeled
Other holiday rentals with a pool

Sapphire Beach Escape VIEWS! HGTV

Good Vibes Only Ocean Villa-Views/Pool/Sundeck/Fun

Sapphire 2bd/2bath Penthouse; Marina & ocean views

New one bedroom condo overlooking Sapphire Beach

Seaview in St. Thomas

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

Escape the Cold/Ocean Front/1BR/1BA/Amazing Views/

2025 Renovated • On Sapphire Beach • King Bed
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- Flamenco Beach
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