Family-friendly vacation rentals in Anna's Retreat

Find and book unique family-friendly homes on Airbnb

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

Condo

4.93 out of 5 average rating, 113 reviews

Wrap Around Balcony w/Amazing Views! Remodeled!

Book Now! Down Island Dream is a 1BR/1BA luxury villa located @Point Pleasant on the East End of St Thomas. 2 Restaurants, 3 pools, nature trail & 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!

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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

4.94 out of 5 average rating, 160 reviews

(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.

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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

4.86 out of 5 average rating, 171 reviews

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.

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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

4.97 out of 5 average rating, 117 reviews

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.

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Top guest favorite

Apartment in Saint Thomas

4.98 out of 5 average rating, 220 reviews

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.

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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

5.0 out of 5 average rating, 207 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!

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Guest favorite

A modern living area features a comfortable seating arrangement with a dark sectional sofa and light accent chairs. Natural light filters through large windows, highlighting the room's stylish decor, including a unique chandelier and a tasteful area rug, all with views of the harbor.

Apartment in Charlotte Amalie

4.95 out of 5 average rating, 153 reviews

Stylish & Luminous 2BR-spectacular water views!

Welcome to a newly renovated 1,800 sq foot 2 bedroom located in the heart of historic Charlotte Amalie! Our space is perfect for travelers who wish to experience the beauty of the US Virgin Island. Each room is oversized, with tall ceilings, and boasts stunning panoramic views of the Caribbean that are sure to take your breath away. The space is as stylish as it is comfortable, with modern furnishings and luxurious touches throughout, yet contextually appropriate for the historic setting.

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Superhost

A serene beach scene displays soft golden sand meeting calm turquoise waters. Gentle waves lap at the shore, while lush greenery frames the view. In the distance, the coastline features rolling hills and scattered islands beneath a clear blue sky dotted with a few clouds.

Condo in East End

4.81 out of 5 average rating, 144 reviews

Sapphire Village Resort Getaway

Kick back and relax in this calm, stylish space. This completely remodeled actual 1 bedroom is beautiful! The views are absolutely amazing. This corner unit has a full kitchen with a full size stove, full size refrigerator, dishwasher, and microwave. The bedroom has a brand new queen size bed with your own tv. The bathroom is completely redone. Just steps from the newly remodeled pool and one of my favorite restaurants on the island. Sudi’s. The crystal clear beach is just a short walk.

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Guest favorite

A serene outdoor space features a private pool surrounded by a sun-soaked patio. Lounge chairs are positioned comfortably nearby, with large sliding glass doors revealing an inviting interior. Lush greenery frames the area, enhancing the sense of seclusion and tranquility.

Condo in Smith Bay

4.84 out of 5 average rating, 290 reviews

Romantic Private Pool Villa@Sapphire. Generator.

Privacy is in a romantic eco-resort, between Sapphire and Lindquist Beaches, backing on to a nature preserve. Fodor's Guide recommends the private pool for"Adam and Eve, Eve an Eve and Adam and Adam". It has a new marble floor; an eco-bathroom with a rain shower, new mattress and smart TV. Historic details like slatted ceilings and four-poster bed. The pool has been rebuilt with antique glass tiles. Contemporary touches : pergola & pool lights, let you create your own experience.

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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

4.95 out of 5 average rating, 145 reviews

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.

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Top guest favorite

An outdoor infinity pool is shown with tranquil waters extending towards the Caribbean Sea. Lush greenery and palm trees surround the area, with views of the coastline and sailboats on the horizon. The sky is partly cloudy, enhancing the serene atmosphere of the setting.

Home in Southside

5.0 out of 5 average rating, 104 reviews

Entire villa with beautiful views! Amazing

Overlooking Bolongo beach. Perfect for couples traveling together but want plenty of privacy as well. 1200 sf covered patio to enjoy sunning, relaxing, dinners with family and friends while being soothed by waves and wonderful breezes. Two bedrooms, each with full baths in main house AND two private apartments below each having the same wonderful views! Perfectly located between Red Hook for ferry to St. John and Havensight for shopping. Catch the beautiful sunrises and sunsets.

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Top guest favorite

A serene beach scene captures clear turquoise waters gently lapping against the shore. Lush greenery cliffs rise in the background, adding natural beauty to the landscape. A small boat and a few swimmers can be seen enjoying the calm sea, enhancing the tranquil atmosphere.

Home in East End

4.97 out of 5 average rating, 157 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.

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