
Holiday rentals with a pool in Anna's Retreat
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Anna's Retreat

Total holiday rentals
Explore 60 holiday rentals in Anna's Retreat

Nightly prices starting at
Anna's Retreat holiday rentals start at $193 NZD per night before taxes and fees

Verified guest reviews
Over 260 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Anna's Retreat holiday rentals include Wi-Fi access

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

4.9 Average rating
Anna's Retreat stays are highly rated by guests—averaging 4.9 out of 5!
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.

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

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.

Ocean View 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

Sail Away II-WOW Beachfront to Paradise Remodeled
Full property generator. 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. 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.

Entire villa with beautiful views! Amazing
Overlooking Bolongo beach. Perfect for couples traveling together but want plenty of privacy as well. 1200 sf covered patio to enjoy sunning, relaxing, dinners with family and friends while being soothed by waves and wonderful breezes. Two bedrooms, each with full baths in main house AND two private apartments below each having the same wonderful views! Perfectly located between Red Hook for ferry to St. John and Havensight for shopping. Catch the beautiful sunrises and sunsets.

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.

View of Magen’s Bay Beach
The apartment is very close to a private beach below. The community is private which has now turn into a gated community. If you love jogging since the traffic is not high the area has jogging or walking. Transportation is needed. President Clinton stayed in this area villa just below. I am retired and I enjoy hosting also I am easy to get along with. There are beach chairs, snorkeling equipment and beach towels available for your use.
Popular amenities for Anna's Retreat rentals with a pool
House rentals with a pool

Villa Bliss - 3 Bedroom Island Oasis

Island Retreat - Generator/Ocean View/Heated Pool

Sleeps 9 - Generator - Central Location - POOL!

IRIE Tides-Sapphire beachfront!

Northside Ocean View Villa • Pool • Near Magens

Waterfront Villa Tryst on Hull Bay (3 bedrooms)

Private Pickleball Court - 5 min walk to Beach

Ylang Ylang - Luxury 2 Suite Villa in Cruz Bay...
Condo rentals with a pool

Rockroom One Bedroom Condo at The Hills Saint John

"H2Oh What a Beach!" condo: Walk-out Beach Access!

Romantic Private Pool Villa@Sapphire. Generator.

Luxury 1/1 Oceanfront @ Sapphire Beach Resort

Pack your Bathing Suit! Warm Weather & Sunshine!

★★★★★ Breathtaking Ocean Views-Private Balcony

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

Seaside Escape at Sapphire Beach Resort
Other holiday rentals with a pool

Private Villa*MagensBay *Ocean front* Private Pool

Villa Hermosa - Beautiful with Pool & Ocean Views

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

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

Hilltop Paradise Vacation Package with Jeep

Sapphire C-Scape:WALKOUT ON SAPPHlRE W/ Generator

Ocean views from every room!

5 Star NEW Luxury Fully Remodeled 1x2 Pool & Beach
When is the best time to visit Anna's Retreat?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $400 NZD | $437 NZD | $438 NZD | $437 NZD | $437 NZD | $437 NZD | $431 NZD | $437 NZD | $437 NZD | $402 NZD | $402 NZD | $419 NZD |
| 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 |
Destinations to explore
- Condo rentals Anna's Retreat
- Rentals with outdoor seating Anna's Retreat
- Rentals with beach access Anna's Retreat
- Apartment rentals Anna's Retreat
- Rentals with a patio Anna's Retreat
- Rentals with a washing machine and dryer Anna's Retreat
- Family-friendly rentals Anna's Retreat
- Guesthouse rentals Anna's Retreat
- Fitness-friendly rentals Anna's Retreat
- Rentals with a hot tub Anna's Retreat
- Rentals with pools U.S. Virgin Islands
- Flamenco Beach
- Magens Bay Beach
- Honeymoon Beach
- Coki Beach
- Cane Garden Beach
- Secret Harbor Beach
- Cinnamon Bay Beach
- Virgin Islands National Park
- Cane Bay Beach
- Limetree Beach
- The Baths
- Peter Bay Beach
- Sun Bay Beach
- Josiah's Bay
- Maho Bay Beach
- Coral World Ocean Park
- Isla Palomino
- Cane Bay
- Cond Marina Lanais
- Paradise Point Tranway
- Brewers Bay Beach
- Cruz Bay
- Lindquist Beach
- Point Udall





