
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.

Cold? 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

"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. Check out our reviews - there's a reason why we're always full!

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.

OceanView! 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

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.

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.

Sea-N-Dipity 1 by the Sea @ Sapphire Resort
Beautiful ocean side condo steps from the breath-taking turquoise Caribbean waters. Spectacular views of St. John Island and the British Virgin Islands. Sapphire beach is a popular destination, known for it's snorkeling, beach life, kayaking, beach side bar and coffee shop. Located on the eastern end of St. Thomas, one mile from Red Hook which provides many conveniences such as shopping, delicious dining, bars and activities. Note: 1 king bed, 1 queen size sleeper sofa.

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

Seascape Villa with private pool in Cruz bay

Vind Lyst - Roof Top Deck & Stunning Ocean Views

Condo by the beach! Condo steps away from the beach!

Private Saltwater Poolside Cottage w/View and Gate

Seaside Lux: Steps to the sand a true oasis!

NEW Villa La Brisa Luxury Hideaway

The Caribbean Farmhouse/Ocean Views, Solar Power

Change Your Perspective at Villa Point of View
Apartment rentals with a pool

Stunning Ocean View w/Balcony~Shades of Sapphire~

Charming Beach Condo w/ Balcony- 2 Pools and Beach

REGATTA R&R

Sail Away II-WOW Beachfront to Paradise Remodeled

Your Perfect Beachfront Condo in Paradise

Seas The Day

Oceanfront Bliss & Perfect Sunsets + Backup Power

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

Paradise at Luxurious Bluebeards Castle Resort

Condo with Northside Views & Back-Up Generator

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

New one bedroom condo overlooking Sapphire Beach

Peaceful 1 Bedroom Near Sapphire Beach

Escape the Cold/Amazing Views/Tropical Trade Winds

“Live For Today” awesome condo on the south side

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 | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £185 | £185 | £185 | £185 | £185 | £185 | £183 | £185 | £185 | £171 | £171 | £178 |
| 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 £74 per night before taxes and fees

Verified guest reviews
Over 270 verified reviews to help you choose

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

Rentals with dedicated workspaces
30 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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