
Holiday 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

HarborHouse-PRIME OCEANFRONT VILLA SAPPHIRE BEACH
Two story oceanfront VILLA with PRIME views of the marina and St. John at SAPPHIRE BEACH RESORT. This 1200 square ft. newly furnished, two story villa sleeps 6. It offers robes, outdoor couch and dining, grill, cable, upstairs and downstairs TV, two bathrooms, washer, dishwasher, and wifi. Relax in the large upstairs bedroom with cathedral wood planked ceilings and plush KING SIZE BED or enjoy lounging outside at one of TWO BALCONIES that offer the best views at Sapphire Beach Resort!

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.

Sunrise Sapphire Beach 2-Corner Unit Balcony
Renovated Studio Condo at Sapphire beach! Corner Unit with large outdoor living area and seating for 8 and tons of natural light! Grill for cooking on the EXTRA LARGE BALCONY. Full Chefs Kitchen and Granite countertops, NEW Lighting, AC unit, Bedding, Bed and all NEW furniture! 55" Smart TV with Netflix access. Beach chairs at Sapphire Beach included in your rental! Memory Foam Bed. This unit is one of best locations in the building. We do not offer cable tv package

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

Private Saltwater Poolside Cottage w/View and Gate

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

Secluded Villa with Ocean Views

NEW Villa La Brisa Luxe Hideaway

Seaside Charm - Beachfront Romantic Getaway!

The Caribbean Farmhouse/Ocean Views, Solar Power

Oceanfront Private Caribbean Resort!

Caribbean Poolside Cottage
Apartment rentals with a pool

Rockroom One Bedroom Condo at The Hills Saint John

SunnySide Villa! 2BR/3BA in Margaritaville resort

Stunning Ocean View w/Balcony~Shades of Sapphire~

Seas The View-Updated & Oceanview @ Sapphire Beach

Villa in Paradise with Private Pool and Generator

Romantic Private Pool Villa@Sapphire. Generator.

Stay in style right on the ocean -Simply the BEST!

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

Private Villa*MagensBay *Ocean front* Private Pool

Resort living at the beach.

Good Vibes Only Ocean Villa-Private Pool-Views!

On the Beach! 1 Min Walk to Dining - STJ Ferry

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

*Margarita-ville Resort* Studio Suite (Sleeps 2)

***Studio Plus @ Wyndham Margaritaville St Thomas*

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 | £190 | £190 | £190 | £190 | £190 | £190 | £187 | £190 | £190 | £190 | £190 | £190 |
| 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 £76 per night before taxes and fees

Verified guest reviews
Over 300 verified reviews to help you choose

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

Rentals with dedicated workspaces
40 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
- 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
- Pelican Cove Beach
- Secret Harbor Beach
- Josiah's Bay
- Gibney Beach
- Caneel Bay Beach
- Maho Bay Beach
- Playa Sun Bay
- Virgin Islands National Park
- Playa Puerto Real
- Playa el Convento
- Pineapple Beach
- Trunk Beach
- Buccaneer Beach




