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

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

Nightly prices starting at
Anna's Retreat vacation rentals start at ﺩ.ﺇ404 per night before taxes and fees

Verified guest reviews
Over 260 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 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

4.9 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!

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!

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

★★★★★ 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. GENERATOR-No power outages to worry about! Great LOCATION-Minutes to Fine RESTAURANTS & THE BEST BEACHES on St Thomas. 1 RESTAURANT- Sun & Sea Bar & Grille right on the water. Fully equipped w/King Bed Queen Sleeper sofa Beach Chairs & Towels Cooler Outdoor Dining WiFi - 100MB OMG Views!

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.

Honeymoon-Worthy w/ Pvt Pool Walk 2 Sapphire Beach
We fell in love with the island of perpetual summer. There's something special about having your own villa w/ a private pool. We also love the garden shower & the location. Pangea, the restaurant on site is phenomenal. The property is so close to our fave spots. Beautiful Sapphire Beach is in walking distance via a gate at the south end of the property. It boasts the Beach Buzz coffee & bfast spot, a Beach bar & grill w/ live music weekly, Paradise Pie pizza & SeaSalt fine dining restaurants.

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

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.

Rockroom One Bedroom Condo at The Hills Saint John
"The Rockroom" is a one bedroom apartment located within The Hills Saint John. This large space with amazing views of Cruz Bay and St Thomas features a large bedroom with King bed, two full baths, a large living area and a full kitchen. There is also a large private patio with a gas grill and patio furniture. Guests staying at Rockroom will also have access to The Clubhouse Bar (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

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

Island Retreat - Generator/Ocean View/Heated Pool

Private Saltwater Poolside Cottage w/View and Gate

Tranquil Desires, Villa

Stone Cottage with a pool and gorgeous view

IRIE Bliss -Beach front

Ylang Ylang - Luxury 2 Suite Villa in Cruz Bay...

Honeycomb Hideaway

Scott Beach Condos #8
Condo rentals with a pool

Stunning Ocean View w/Balcony~Shades of Sapphire~

Serene Beach Condo | Sapphire | 1BR | 2 Pools

SunnySide Villa! 2BR/3BA in Margaritaville resort

Sapphire Blue Sea View

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

Luxury 1/1 Oceanfront @ Sapphire Beach Resort

Stay in Style right on the Ocean -Simply the BEST!

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

Come stay where the views steal the show daily!

Private Villa*MagensBay *Ocean front* Private Pool

Sapphire Beach Beachfront W/Generator & Dishwasher

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

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

Escape to Summer/Tropical Trade Winds/3 Pools!

B7 - Point Pleasant Resort

“Live For Today” awesome condo on the south side
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.ﺇ903 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ841 | ﺩ.ﺇ841 | ﺩ.ﺇ878 |
| 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 |
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