
Vacation rentals with a pool in Anna's Retreat
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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.

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

"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. Be among the many visitors who LOVE this totally renovated condo.

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!

C'est Jolie - Views! Views! Views!
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.

Hillside Hideaway
Perfect getaway for island romance, 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.

VIEWS! Condo by Magen's Beach w/ 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

Lazy Loft: Tiny Room Loft and Private Outdoor Bath
Location, Location, Location…we're a short, 1/2 mile walk to Red Hook, the most happening place on the island (Including St John Ferry, grocery, marina, and 20+ eateries and bars) and Secret Harbour Beach. We’re nestled within a large home with a tropical themed backyard. We have a Saltwater Pool, 5 decks, BBQ grill, Honor Bar, outdoor dining areas, lounge chairs, hammocks, Corn-Hole, and other bar games. Help yourself to our snorkeling gear, Ice chests or beach chairs. ADULT/TEEN ONLY.

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.

Stylish Beach Condo located at Sapphire- 2 Pools
Come and relax in our beautiful condo located East End at Sapphire Village. Fully furnished with a modern, beachy vibe to match the glimmering turquoise waters seen from the windows. Property has hotel amenities including 2 pools, great snorkeling, 3 restaurants, beach bar, coffee shop/deli all on property! The unit is a studio w/queen bed, full kitchen and bathroom. Everything is provided in the condo for you to come and fully relax! 20 min from airport.

Villa La Realeza - Award Winning Design - VIEWS!
Welcome to Villa La Realeza by Virgin Islands Vacation. This Villa is the perfect island vacation rental in St Thomas, and is located inside the guard gated Point Pleasant Resort. The Villa offers the perfect blend of relaxation & adventure. Relax by the pools or simply enjoy amazing views from the private wrap around patio with views of St John & Tortola islands. NO PETS allowed, $250 fee if violated.
Popular amenities for Anna's Retreat rentals with a pool
House rentals with a pool

Island Retreat-Amazing Views/Heated Pool/Generator

Secluded Villa with Ocean Views

Villa Fratelli Garden

Tranquil Desires, Villa

Oceanfront Private Caribbean Resort!

Caribbean Poolside Cottage

Texas Embassy

Caribbean Cottage Near the Sea
Condo rentals with a pool

Sapphire Beach Paradise Condo

Rockroom One Bedroom Condo at The Hills Saint John

Stunning Ocean View w/Balcony~Shades of Sapphire~

Seas The View-Updated & Oceanview @ Sapphire Beach

HarborHouse-PRIME OCEANFRONT VILLA SAPPHIRE BEACH

REGATTA R&R

*GORGEOUS* 2BR 2BA PRESIDENTIAL St thomas USVI

Salt Life at Sapphire Beach
Other vacation rentals with a pool

Island Timin' Elysian Cowpet Bay Beach Resort USVI

Cold? Book Now! Caribbean Sunshine! Amazing Views!

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

Leave Winter Behind • Hello Island Life & Sunshine

Sunrise Cottage - Secluded, Romantic, Private

Escape the Cold/Amazing Views/Tropical Trade Winds

Sapphire Sunrise: 2 Story Ocean Villa Luxe Reno

Oceanfront w/ Balcony, Pool, Generator & Fast WiFi
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 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ903 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 |
| 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 vacation rentals with a pool in Anna's Retreat

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

Nightly prices starting at
Anna's Retreat vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

Verified guest reviews
Over 300 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Anna's Retreat vacation rentals include wi-fi 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
- Honeymoon Beach
- Limetree Beach
- Magens Bay Beach
- Cane Garden Beach
- Coki Beach
- Oppenheimer Beach
- Cinnamon Bay Beach
- Cane Bay Beach
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