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.

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Top Guest favourite
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, 188 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. Be among the many visitors who LOVE this totally renovated condo.

Guest favourite
A wooden bench with a sign reading 'SAIL AWAY' is positioned on a patio, overlooking the vibrant blue waters of a beach. Lush green foliage and palm trees frame the view, with rolling hills visible in the distance under a partly cloudy sky.
Condo in East End
4.94 out of 5 average rating, 123 reviews

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!

Guest favourite
An open-concept living area features high wooden ceilings and large sliding glass doors, providing unobstructed views of the ocean and surrounding islands. A dining table and chairs are visible alongside a turquoise cabinet, with a ceiling fan above for comfort.
Condo in Saint Thomas
4.93 out of 5 average rating, 105 reviews

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.

Top Guest favourite
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, 200 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.

Guest favourite
A panoramic view reveals vibrant turquoise waters and several nearby islands, bordered by lush greenery. The sky is partially filled with fluffy clouds, and the distant shoreline features contrasting structures amidst the natural landscape.
Villa in St. Thomas
4.83 out of 5 average rating, 263 reviews

Amazing Villa in Paradise: Views of 9 Islands

You will love this villa's amazing views, and perfect location on the East End of St Thomas. This villa has all new furniture, a gorgeous kitchen, remodeled bath, high end sheets and towels, beach towels, beach chairs, snorkel gear, a 42" TV, great WiFi and so much more. You are 50 steps from the pool and one of our on-site restaurants, plus 5 mins to 4 of the best beaches on island. I'll provide details on all the beaches, restaurants, bars, stores and more. You will absolutely love it!

Top Guest favourite
A spacious pool area is highlighted by a refreshing private pool, surrounded by a wooden deck. Two black loungers provide comfortable seating, while colorful inflatables add a playful touch to the clear water. The setting is brightened by large glass doors and subtle outdoor lighting.
Home in East End
4.96 out of 5 average rating, 111 reviews

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.

Guest favourite
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, 146 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 favourite
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, 106 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 favourite
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
4.95 out of 5 average rating, 109 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.

Guest favourite
A cozy living area features a comfortable sofa with a decorative pillow, alongside a sleek wooden coffee table. Large glass doors open to a private balcony with outdoor seating, showcasing views of the sparkling turquoise waters and surrounding landscape.
Condo in East End
4.89 out of 5 average rating, 288 reviews

Ocean View Sapphire Condo-Balcony & King Bed

Located at Sapphire Village-Amazing balcony and views of Sapphire Beach and its glimmering turquoise waters. Short walk to the beach and beach bar! 1 King bed, and one queen sleeper sofa. Property has hotel amenities including 2 pools, great snorkeling, 3 restaurants, beach bar, coffee shop & deli! Secure, safe location. Taxis are readily available nearby for rides to grocery stores, Red Hook for dinner, St. John Ferry, local beaches. 25 min from airport!

Guest favourite
A sandy beach scene is depicted, featuring clear turquoise waters and a bright blue sky dotted with clouds. Palm trees and lush greenery frame the area, while groups of people enjoy the beach. Lounge chairs are visible on the sand, inviting relaxation.
Condo in St. Thomas
4.85 out of 5 average rating, 170 reviews

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

Guest favourite
A bright seating area features two modern white armchairs positioned near large windows, offering unobstructed views of the ocean and sky. A wooden side table with a lamp and decorative elements complements the room's light colors and contemporary design.
Condo in Northside
4.92 out of 5 average rating, 165 reviews

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

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

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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 $176 NZD per night before taxes and fees

  • Verified guest reviews

    Over 300 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

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

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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!