
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.

"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.

Charming Beach Condo w/ Balcony- 2 Pools and Beach
Located at Sapphire Village. Amazing balcony and views of Sapphire Beach and its turquoise waters. Short walk to the beach and beach bar! Completely renovated with new furniture- 1 KING bed, and one queen sleeper sofa. Property has hotel amenities including 2 pools, great snorkeling off of the beach, 3 restaurants, beach bar, coffee shop & deli! Secure safe location. Taxis are readily available for rides to grocery stores, Red Hook for dinner, St. John Ferry, beaches. 25 min from airport!

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

★★★★★ Breathtaking Ocean Views-Private Balcony
★★★★★ REVIEWS ON MULTIPLE SITES. Luxurious Updated 1 BR/1 BA Condo w/WRAP AROUND BALCONY & BREATHTAKING views of St. John, BVIs, & CARIBBEAN SEA! Point Pleasant Amenities: 3 Amazing POOLS & INTIMATE BEACH. NEW FURNISHINGS 2019. Great LOCATION-Minutes to Fine RESTAURANTS & THE BEST BEACHES on St Thomas. 2 RESTAURANTS - Sun & Sea Bar & Grille right on the water & Ocean180. Fully equipped w/King Bed Queen Sleeper sofa Beach Chairs & Towels Cooler Outdoor Dining WiFi - 100MB OMG Views!

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.

Caribia Cottage-Elegant Villa w/Private Pool
Caribia Cottage is located in a private Estate with access only through an electronic gate. The spectacular panoramic view of the St. Thomas Harbor is unforgettable and one which many a famous star toasted to when the property was formerly owned by a celebrated Broadway Producer. Walk just two steps from the Cottage into the spacious swimming pool. Enjoy gazing at the busiest Harbor in the Caribbean, as the mega yachts, seaplanes and cruise ships come and go.

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

Free POOL Heater - See details - Magens Bay

Ocean View Retreat- 2BR/2BA Heated Pool, Generator

New Listing! New remodel steps to beach & pool!

NEW Villa La Brisa Luxe Hideaway

Villa Fratelli Garden

Oceanfront Private Caribbean Resort!

Caribbean Poolside Cottage

Texas Embassy
Condo rentals with a pool

Rockroom One Bedroom Condo at The Hills Saint John

Sapphire in the Sand

Stunning Ocean View w/Balcony~Shades of Sapphire~

HarborHouse-PRIME OCEANFRONT VILLA SAPPHIRE BEACH

*GORGEOUS* 2BR 2BA PRESIDENTIAL St thomas USVI

Villa in Paradise with Private Pool and Generator

Salt Life at Sapphire Beach

Beachfront • King • W/D • By RH • Pool • Marina
Other vacation rentals with a pool

Island Timin' Elysian Cowpet Bay Beach Resort USVI

3 Pools/2Restaurants/Hilltop Condo/Amazing Views!

NEW - Modern Remodel, Magens View, pool, Deck,

"On the Rocks" Ocean Front 1BR/1BA Amazing Views!

Tropical Hideaway! Garden View @Point Pleasant

Sunrise Cottage - Secluded, Romantic, Private

Tropical Sands | Elysian Beach Resort | St. Thomas

Oceanfront luxury penthouse
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 | $349 CAD | $349 CAD | $349 CAD | $349 CAD | $349 CAD | $349 CAD | $344 CAD | $349 CAD | $349 CAD | $349 CAD | $349 CAD | $349 CAD |
| 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 $140 CAD 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 and kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Anna's Retreat vacation 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
- Honeymoon Beach
- Limetree Beach
- Magens Bay Beach
- Mosquito Bay Beach
- Cane Garden Beach
- Coki Beach
- Oppenheimer Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Peter Bay Beach
- Secret Harbor Beach
- Pelican Cove Beach
- Gibney Beach
- Josiah's Bay
- Caneel Bay Beach
- Playa Sun Bay
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- Virgin Islands National Park
- Playa Puerto Real
- Trunk Beach
- Pineapple Beach
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