
Holiday rentals with a pool in Anna's Retreat
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Anna's Retreat
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

Sail Away II-WOW Beachfront to Paradise Remodeled
Sail Away II at Sapphire Beach Resort and Marina is located on the beachfront just steps away from the sparkling Sapphire Beach. The patio leads you to a dazzling infinity pool and the option of 2 immaculate beaches. Golden sand, pristine Caribbean water and amenities galore await you. No need to leave the tranquility of your room thanks to the many home furnishings within your vacation paradise. Beach level, beachfront & lush surroundings is yours to escape the hub of city life. KING SIZE BED!

SunnySide Villa! 2BR/3BA in Margaritaville resort
Walk to the beach from Sunny Side Villa @Pineapple Village! Pineapple Village sits inside the Margaritaville Resort! It has its own pool area, beach access, and access to hotel restaurants cafe and bars on site. Safe secure location. Taxis available for a ride to grocery stores, Red Hook for dinner, St. John Ferry, local beaches, or airport. It’s great for any vacation. The 2-Bedroom Villa can hold up to 4 people in beds, and has 2 large sofas. It has 2 master bedrooms and 3 full Baths.

"H2Oh What a Beach!" condo: Walk-out Beach Access!
"H2Oh What a Beach!" condo Building A of Sapphire Beach Resort & Marina: ground floor unit with direct access to one of the most beautiful beaches in the Caribbean. Steps away from Sea Salt fine dining restaurant, Sapphire Beach Bar, Paradise Pie pizza, and Beach Buzz coffee shop. A mile from Red Hook featuring many restaurants & island ferries. Great beach, swimming, snorkeling, parasailing, and relaxing right outside your door. Check out our reviews - there's a reason why we're always full!

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.

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.

OceanView! 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

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.
Popular amenities for Anna's Retreat rentals with a pool
House rentals with a pool

Vind Lyst - Roof Top Deck & Stunning Ocean Views

Seascape Villa with private pool in Cruz bay

Sleeps 9 - Generator - Central Location - POOL!

Secluded Villa with Ocean Views

Tranquil Desires, Villa

Caribbean Poolside Cottage

Texas Embassy

Wild Ginger at Casa Tre Fiori
Apartment rentals with a pool

Rockroom One Bedroom Condo at The Hills Saint John

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

Villa in Paradise with Private Pool and Generator

Romantic Private Pool Villa@Sapphire. Generator.

Salt Life at Sapphire Beach

★★★★★ Breathtaking Ocean Views-Private Balcony

Your Perfect Beachfront Condo in Paradise

Seas The Day
Other holiday rentals with a pool

Steps to Sapphire Beach: 1br/2ba Near Red Hook

Paradise at Luxurious Bluebeards Castle Resort

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

Villa View Caribe

Direct Ocean front , steps to the Sandy Beach

Condo with Northside Views & Back-Up Generator

Exquisite Hillside Condo 2 - St. Thomas, U.S.V.I.

“Live For Today” awesome condo on the south side
When is the best time to visit Anna's Retreat?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $320 SGD | $320 SGD | $320 SGD | $320 SGD | $320 SGD | $320 SGD | $316 SGD | $320 SGD | $320 SGD | $294 SGD | $294 SGD | $307 SGD |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°C |
Quick stats about holiday rentals with a pool in Anna's Retreat

Total holiday rentals
Explore 70 holiday rentals in Anna's Retreat

Nightly prices starting at
Anna's Retreat holiday rentals start at $128 SGD per night before taxes and fees

Verified guest reviews
Over 270 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
70 of Anna's Retreat holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Anna's Retreat rentals

4.8 Average rating
Anna's Retreat stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with pools U.S. Virgin Islands
- Flamenco Beach
- Limetree Beach
- Honeymoon Beach
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Secret Harbor Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Virgin Islands National Park
- Peter Bay Beach
- Josiah's Bay
- Sugar Beach
- Maho Bay Beach
- Coral World Ocean Park
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- The Baths
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