Family-friendly vacation rentals in Anna's Retreat

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Top-rated family-friendly rentals in Anna's Retreat

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

An outdoor table made of wood is set with two wine glasses and a bottle of wine. Views of the ocean and palm trees are visible in the background, with soft clouds and a blue sky enhancing the tranquil setting.

Condo in East End

Your Perfect Beachfront Condo in Paradise

Highly Desired Corner Unit right on Gorgeous Sapphire Beach. It's all here: Warm weather, White sand, Fun and Relaxation. Sapphire Beach is considered to be one of the most beautiful beaches in St Thomas. Your second floor beachfront condo in Building C is just 7 easy steps to the beach and in a perfect central location for quiet relaxation and convenient access to the facilities. Condo and complex have full backup generator power. No worries at all during occasional Island power outages.

Indoor spacesKitchenDecor

4.94 out of 5 average rating, 112 reviews

Guest favorite

A serene ocean view is presented from a patio, featuring soft waves gently lapping at a sandy beach. Lush greenery and lounge chairs are visible on the shore, while a palm tree sways in the foreground under a bright blue sky with scattered clouds.

Guest suite in Southside

(Upper Level) Peaceful Getaway in Frenchman Bay

Indulge in the serenity of our Rock City retreat, where breathtaking ocean views meet refined comfort. Enjoy the patio, WiFi, AC, and eco-friendly solar energy. Ideally situated for families and travelers alike, our haven is close to Morningstar Beach, Westin conferences, and Havensight shopping. For added convenience, rent an SUV or utilize taxi services. Click on our Group Villa listing which offers ample space for up to 15 guests. For a seamless stay, review listing details and house rules.

Indoor spacesFamilyWalkability

4.94 out of 5 average rating, 161 reviews

Top guest favorite

An outdoor balcony offers expansive ocean views, featuring a comfortable lounge chair and a dining set with cushioned seating. The blue waters of the Atlantic extend towards distant islands, framed by bright blue skies and white clouds, enhancing the serene atmosphere.

Condo in Lovenlund Gns

2 Bed Ocean Views, Gated Community & Backup Power

The property is equipped with a full automatic backup generator, ensuring uninterrupted comfort should local power outages occur. Saltwater Dreams, a beautiful two-bedroom St. Thomas condo located in the prestigious gated community of Mahogany Run. This ocean view condo in the U.S. Virgin Islands offers breathtaking views of the Atlantic Ocean and the neighboring British Virgin Islands, creating the perfect setting for couples, families, and friends seeking an unforgettable Caribbean getaway.

Indoor spacesKitchenLayout

4.97 out of 5 average rating, 117 reviews

Guest favorite

A well-appointed sleeping area features a spacious bed covered with a soft blue blanket, situated near two artwork pieces depicting serene landscapes. A bedside table holds a small plant, and a lamp provides gentle lighting, enhancing the room's tranquil feel.

Apartment in Saint Thomas

Traveler's Hideaway

Come enjoy this quiet, cozy, air conditioned 2 bedroom 1 bath rental space with stunning mountain views. Wake up to fresh, cool, calming breezes compliments of world famous Magen's Bay which is only a 5 to 7 minutes drive away. Apartment comes with its own entrance, kitchen and living area and caters to all, from a single traveler, couples, friends or a small family with children. Amenities include high speed internet and TV. Located within a 10 minutes drive to downtown Charlotte Amalie.

Indoor spacesKitchenSleep quality

4.86 out of 5 average rating, 171 reviews

Top guest favorite

Apartment in Saint Thomas

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.

Indoor spacesFamilyHospitality

4.98 out of 5 average rating, 220 reviews

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

"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!

KitchenFamilyAir conditioning

5.0 out of 5 average rating, 207 reviews

Top guest favorite

Villa in Saint Thomas

NEW WATERFRONt Villa at Magens Bay, hot tub, Jeep

This new waterfront villa is conveniently located steps away from the Platform beach and 5 min. drive to famous Magens Bay Beach. Enjoy morning coffee watching turtles or Eagle rays flying above the turquoise water right from your balcony. This extraordinary furnishing and modern feel will provide cozy and exceptional vacation for your family and friends. The outdoor space offers great relaxing area overlooking the Caribbean sea. Hot tub brings the resort feel with the privacy you deserve.

Indoor spacesFamilyHot tub

4.89 out of 5 average rating, 175 reviews

Top guest favorite

Villa in Anna's Retreat

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

Gorgeous Caribbean paradise w/ a salt water pool. Sleeping for 10 including 3 private bedrooms w/ensuite bathrooms. Sprawling living & fully stocked kitchen. Additional Queen sleepers in living & master + 1/2 bath. Enjoy stunning ocean views w/ direct line of site over to White Bay in the BVI, Tortola, Hans Lollik & Mandahl Beach/Salt Pond. The villa is equipped w/multiple patio areas & stunning pool w/ soothing trade-winds that blow through the property for comfortable outdoor living.

Indoor spacesFamilyAir conditioning

4.98 out of 5 average rating, 101 reviews

Top guest favorite

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

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.

Indoor spacesFamilyGrill

4.95 out of 5 average rating, 146 reviews

Guest favorite

Home in East End

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.

FamilyIndoor spacesCheck-in

4.97 out of 5 average rating, 158 reviews

Top guest favorite

A balcony table is set with two plates of breakfast, accompanied by cups, overlooking the tranquil blue waters of the Caribbean Sea. The rhythmic sound of waves enhances the serene dining experience, with a clear sky and fluffy clouds visible in the background.

Condo in Saint Thomas

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 ocean, 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! 🌴

Indoor spacesKitchenValue

4.97 out of 5 average rating, 172 reviews

Top guest favorite

Villa in Charlotte Amalie

Tropical Modern Loft | SoHo Style | Concierge

Single night bookings welcome! A luxe art loft experience in the heart of St. Thomas, this exclusive space in a convenient central location provides a chic home base, with sleek design, concierge options, + creative vibes. Perfect for both adventure and serenity. Ample space to lounge, with a balanced historic/contemporary aesthetic, and near beaches, restaurants, historic landmarks, boutiques, + ferry/airport/transportation. Our cafe/bar and art gallery are right downstairs.

KitchenIndoor spacesCheck-in

4.99 out of 5 average rating, 158 reviews