
Vacation 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.

"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.

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.

Salt Life at Sapphire Beach
Salt Life condo is located within Sapphire Village, at beautiful Sapphire Beach, close to Red Hook, and Coral World. You’ll love Salt Life condo because of the 1 minute walk to Sapphire Beach, the views, the ambiance, and a 2 minute drive to Red Hook. Salt Life condo is good for couples, solo adventurers, and business travelers. Are your dates in Salt Life already booked? Check out our other condo called Beachtime! at Sapphire Beach, also in the Dominica building, and listed on Air BnB.

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.

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 Condo Perfect Sunsets Backup Generator!
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.

Sea Dreams at Regatta Point Villas
Regatta Point Villas is located in Bolongo Bay, St. Thomas. This spacious condo (2 full baths and 1 bedroom) features 1000sq.ft. of living space and is located steps away from the pool. It has beautiful ocean views from each room. Bolongo beach is a short walk and has great snorkeling. 2 Tennis Courts, basketball hoop, and 3 pools are all accessible and steps away from the ocean. A short drive to Havensight and Redhook with many beaches and restaurants to choose from.

Breathtaking Views from Sapphire Village
Enjoy our studio unit located in Sapphire Village Condominium development! Our unit is smoke-free, pet-free, fully air conditioned, and offers breathtaking views of neighboring USVI and BVI. We are offering a vacation home with the comforts that we would want while we are vacationing on the island. The unit features a king bed, new sliding doors to the balcony as well as a new split air conditioning unit. New internet router January 2024

Ocean View Studio • Near Magens • Pool & Generator
Wake up to sweeping ocean vistas just 5 min from iconic Magen's Bay Beach. This remodeled studio seats you on the hillside with ocean views. • Shared pool • Back-up generator & fast Wi-Fi • King bed • Full kitchen & beach gear (snorkels, chairs, umbrella) Minutes to restaurants, Red Hook ferries and island adventures. Book your carefree St. Thomas escape today! We highly recommend renting a car to get around the island.
Popular amenities for Anna's Retreat rentals with a pool
House rentals with a pool

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

Private Saltwater Poolside Cottage w/View and Gate

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

Private Pickleball Court - 5 min walk to Beach
Condo rentals with a pool

SunnySide Villa! 2BR/3BA in Margaritaville resort

Seas The View-Updated & Oceanview @ Sapphire Beach

REGATTA R&R

*GORGEOUS* 2BR 2BA PRESIDENTIAL St thomas USVI

Villa in Paradise with Private Pool and Generator

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

Beachfront • King • W/D • By RH • Pool • Marina

Sapphire Village Resort Getaway
Other vacation rentals with a pool

Private Villa*MagensBay *Ocean front* Private Pool

Good Vibes Only Ocean Villa-Private Pool-Views!

Condo with Northside Views & Back-Up Generator

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

Oceanfront, 3 POOLS, Central Location, Generator!

Tropical Sands | Elysian Beach Resort | St. Thomas

***Studio Plus @ Wyndham Margaritaville 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 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | 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
 - Mosquito Bay Beach
 - Cane Garden Beach
 - Coki Beach
 - Oppenheimer Beach
 - Cinnamon Bay Beach
 - Cane Bay Beach
 - Peter Bay Beach
 - Pelican Cove Beach
 - Gibney Beach
 - Josiah's Bay
 - Secret Harbor Beach
 - Caneel Bay Beach
 - Maho Bay Beach
 - Playa Sun Bay
 - Virgin Islands National Park
 - Playa Puerto Real
 - Playa el Convento
 - Trunk Beach
 - Pineapple Beach
 - Buccaneer Beach