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.

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Top guest favorite
Condo in VI
4.92 out of 5 average rating, 101 reviews

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!

Top guest favorite
Condo in East End
4.96 out of 5 average rating, 135 reviews

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

Guest favorite
Apartment in East End
4.96 out of 5 average rating, 140 reviews

Salty Loft 1 King Loft Bed

Location, Location, Location…we're a short, 1/2 mile, walk to Secret Harbour Beach or Red Hook, the most happening place on the island: Including St John Ferry, grocery, pharmacy, Gas, Marina, and 20+ eateries and bars. We’re nestled within a large home with a tropical themed backyard. We have a Pool, 5 decks, BBQ grill, Honor Bar, outdoor dining areas, lounge chairs, hammocks, Corn-Hole, and other bar games. Help yourself to our snorkeling gear, Ice chests or beach chairs. ADULT/TEEN ONLY.

Top guest favorite
A sandy beach offers a serene view featuring clusters of leafy trees providing shade. The calm turquoise waters are visible in the background under a clear blue sky. Beach seating is scattered along the shoreline, inviting relaxation and enjoyment of the landscape.
Condo in East End
5 out of 5 average rating, 194 reviews

"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!

Top guest favorite
A cozy living area is equipped with a dark blue sofa, a stylish lamp, and a wooden TV stand. A vibrant rug is placed on the floor, and natural light filters through the white window curtains. A decorative plant adds a touch of greenery to the space.
Apartment in Saint Thomas
4.98 out of 5 average rating, 203 reviews

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.

Top guest favorite
A spacious outdoor patio is featured with a dining table and colorful chairs, offering unobstructed ocean views. Large sliding glass doors lead to the living area, allowing natural light to fill the space. A gentle breeze and serene scenery are prominent.
Condo in Northside
4.99 out of 5 average rating, 157 reviews

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

Guest favorite
A panoramic view showcases the vibrant turquoise waters of the ocean, dotted with small islands in the distance. Lush greenery frames the foreground, while a sailboat floats gently on the water under a sky filled with soft clouds.
Condo in Saint Thomas
4.87 out of 5 average rating, 155 reviews

Million Dollar Views: 2 mins to Beach, Pool, more

One of the BEST places in St Thomas, with a gorgeous kitchen, bathroom, comfortable king bed and teak furniture. This villa is 20 feet over the water, so you see fish swim by and enjoy sounds of the waves below. High end sheets, towels, beach towels, beach chairs, snorkel gear, soap, shampoo, conditioner, plus a new 55" TV and high-speed WiFi. 3 pools and 2 restaurants on property, plus I provide details on all the best beaches, restaurants, bars, stores and more. You will LOVE it!

Top guest favorite
A marina scene is displayed, featuring a variety of sailboats and yachts moored alongside a serene blue waterway. Lush green palm trees frame the view, while distant islands are visible against a clear sky with a few fluffy white clouds.
Condo in East End
4.99 out of 5 average rating, 230 reviews

Stunning Ocean View w/Balcony~Shades of Sapphire~

Beautiful ocean view, top floor studio with balcony at Sapphire Village is perfect for two guest and features a queen size bed. Kitchen and private balcony with spectacular views. Five minute walk to Sapphire Beach, two large pools, two great casual restaurants, coffee shop, taxi stand, and laundromat all on site. The marina has several day excursion options to keep your days full. Sailing trips, parasailing, or rent a wave runner. Everything you need is right on the property.

Top guest favorite
The living area features a spacious sofa and a patterned armchair arranged around a coffee table. Large sliding glass doors provide a view of the ocean and access to the balcony. A dining table with chairs is positioned near the window, allowing for bright natural light.
Condo in St. Thomas
4.96 out of 5 average rating, 153 reviews

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! 🌴

Top guest favorite
The spacious living area features two light-toned sofas arranged around a glass coffee table, with a cozy bean bag on the floor. Natural light enters through two well-sized windows, creating an airy ambiance complemented by a modern floor lamp and a potted plant.
Apartment in Charlotte Amalie
5 out of 5 average rating, 122 reviews

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.

Top guest favorite
A bright living area features large windows revealing ocean views. Natural light fills the space, which includes a sofa, dining table with blue placemats, and decorative plants. A wall-mounted flat-screen TV adds to the modern appeal. The color palette emphasizes calming tones.
Condo in Southside
4.96 out of 5 average rating, 116 reviews

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.

Superhost
A tranquil resort pool is highlighted in this image, featuring clear blue water and surrounded by lush palm trees. An open shelter overlooks the pool area, with a backdrop of a striking sunset casting warm hues across the sky.
Condo in East End
4.81 out of 5 average rating, 166 reviews

Premium Oceanfront Sapphire Beach Resort & Marina

Experience St. Thomas's premier oceanfront resort. Our ground-floor condo offers stunning St. John views, a one-minute walk to Sapphire Beach, and free beach lounges. Enjoy on-site dining, bars, a coffee shop, car rental, and transport services. Exciting water activities, like fishing charters and jet ski rentals, await. Red Hook's vibrant dining scene, marina, and ferry service to neighboring Islands is just a mile away. Enjoy our newly renovated bathroom.

Popular amenities for Anna's Retreat rentals with a pool

When is the best time to visit Anna's Retreat?

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Avg. priceG$52,011 GYDG$52,011 GYDG$52,011 GYDG$52,011 GYDG$52,011 GYDG$52,011 GYDG$51,384 GYDG$52,011 GYDG$52,011 GYDG$47,833 GYDG$47,833 GYDG$49,922 GYD
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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 G$20,888 GYD per night before taxes and fees

  • Verified guest reviews

    Over 270 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

    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!