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Family-friendly vacation rentals in Anna's Retreat

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Anna's Retreat family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A balcony features a round table set for two, accompanied by two chairs. A vase with blooming flowers sits at the center, while the backdrop displays a scenic view of the ocean and distant islands, complemented by a partly cloudy sky.
Condo in Cruz Bay
4.94 out of 5 average rating, 51 reviews

BEAUTIFUL GRANDE BAY STUDIO CONDO W/ GREAT VIEWS

AlexisRating, 5 stars1 month ago
We had a wonderful stay! The place was perfect and I would not want to stay anywhere else. It was very clean, had a nice view, and was extremely walkable to Cruz Bay restaurants. The studio was a good size for my husband and our 2 kids. The resort and the amenities were great. Everyone was super nice and helpful. The pool was warm and the hot tub very nice. There were elevators which was nice for me being very pregnant. The staff were very friendly and willing to help with anything. Would 100% stay here again.
Top guest favorite
The living area features a blend of comfortable seating with a wicker style sofa and armchairs. A ceiling fan promotes airflow, while a flat-screen television is mounted for entertainment. Large sliding doors offer a view of the outdoor space and the Caribbean beyond.
Condo in East End
4.96 out of 5 average rating, 119 reviews

BEST REVIEWS on the East End - HANDS DOWN!

StephanyRating, 5 stars1 week ago
We had a wonderful stay at Sharon's condo. The highlight was being able to sit outside and enjoy the view of the beach and ocean!
A panoramic view captures the vibrant colors of a sunset, with hues of orange and pink reflected in the sky. Rolling hills and lush greenery surround a calm bay, where the water meets the horizon, showcasing the beauty of St. Thomas.
Home in Cruz Bay
4.69 out of 5 average rating, 64 reviews

Charming One Bed Cottage with Hot Tub and Views!

OliviaRating, 5 stars1 month ago
This place was AMAZING!!! The views were spectacular. Perfectly suited for a couple wanting to enjoy a romantic getaway on a beautiful island.
Guest favorite
A panoramic view of Cowpet Bay showcases a vibrant blue waterscape dotted with various boats. The shoreline is framed by lush greenery, while distant hills rise against a partly cloudy sky, enhancing the scene's tranquil atmosphere.
Condo in East End
4.99 out of 5 average rating, 77 reviews

Sunkissed Serenity -Island Chic Home at Cowpet Bay

IreneRating, 5 stars3 weeks ago
To say Keshri’s apartment was fabulous would be an understatement! The view from the balcony was nothing short of breathtaking—like a living postcard or a dreamlike screensaver. Each morning, we sipped our coffee while watching catamarans glide across the turquoise sea—pure serenity. The walk to the pristine beach was quick and easy, making it effortless to enjoy the sun and sand whenever we wished. Great restaurants were just a short walk or drive away, and we also discovered a few hidden-gem beaches nearby that were perfect for exploring and snorkeling. On evenings we chose to stay in, the well-appointed kitchen made cooking simple and enjoyable. With grocery stores close by, it was easy to stock up and feel right at home. We had an unforgettable week at Keshri’s place and would highly recommend it to anyone seeking a peaceful, picture-perfect island escape. Goodbye for now—and see you again, USVI St. Thomas. You truly stole our hearts!
Superhost
A vibrant sign featuring the name 'Margaritaville' is showcased, accompanied by stylized palm trees and a parrot. The colors are bright and tropical, reflecting the lively atmosphere associated with this popular destination.
Condo in Saint Thomas
4.67 out of 5 average rating, 3 reviews

Resort on the Beach! Enchance cleaning.Great area!

DonnaRating, 5 stars48 months ago
This property is wonderful. The resort staff is amazing, the room was perfect, and everything we wanted to do was only a taxi cab ride (or short walk) away. We will definitely look for Janee’s place again when we come back to St. Thomas!
Top guest favorite
A sandy beach is surrounded by tall palm trees, with lounge chairs arranged in rows facing the clear turquoise water. Gentle waves can be seen lapping at the shore, while several boats are anchored in the distance under a bright blue sky.
Condo in East End
4.85 out of 5 average rating, 41 reviews

Beautiful Caribbean Beachfront Vacation Rental

DonnaRating, 5 stars4 months ago
Condo unit was exactly as described. Had one issue with the refrigerator and it was resolved immediately. The location at Elysian Bay was one of the best resort locations with a private beach, amazing swimming pool area and two great restaurants on site. There is a grocery store located only a few miles away for those that wish to cook in. Nearby community of Red Hook offered the party vibe feel along with a variety of restaurants. The location of this unit on St Thomas island couldn't have been better. I will highly recommend this place to anyone looking for an island getaway without the multitudes of people that an all inclusive contains.
Guest favorite
A covered deck area features a hot tub, two lounge chairs, and a dining table set for two. Lush greenery surrounds the space, and a stunning view of the bay and hills is visible through the railing, creating a serene atmosphere.
Cottage in Cruz Bay
4.95 out of 5 average rating, 76 reviews

Romantic Cottage - Stunning Ocean Views, Hot tub.

tiffanyRating, 5 stars1 month ago
enjoyed every minute at meritage! You barely hear traffic there, just waves and nature.. spectacular views and privacy..I was on the balcony every chance I had just staring off into the distance.. so relaxing! The place was perfect for the two of us. Close enough to cruz bay for dinner etc, but far enough out that it was peaceful and relaxing. They have a bigger house right next store that I was worried would be loud, but honestly barely heard them. We will definitely stay there again on our next visit if available!
Superhost
A serene beach scene is depicted at Cowpet Bay, featuring soft sandy shores lined with gentle waves reflecting the pastel colors of the sky. The resort is visible in the background, framed by tropical palm trees.
Condo in St. Thomas
5 out of 5 average rating, 21 reviews

St. Thomas-Elysian Beach, Studio Parlor #1

DavidRating, 5 stars14 months ago
That was a great stay, nice views, and very close to beach. Note that it is a murphy bed / pull down bed.

Family- and pet-friendly home rentals

Superhost
A wooden deck is seen, painted in a warm orange hue, featuring two chairs positioned beside potted plants. A charcoal grill stands ready for use, with lush greenery surrounding the area, providing a serene outdoor space for relaxation.
Apartment in St. Thomas
4.71 out of 5 average rating, 317 reviews

Breezy Beautiful Northside Cottage

JoanRating, 5 stars3 months ago
Marvin's place was awesome! He was super responsive, always there if we had questions. I wish every Airbnb was like his. He helped us tons, and it really felt like home. He even left us fresh fruit and local goodies – such a nice touch! Definitely recommend it. The view was amazing every morning too. Thanks for everything!
Top guest favorite
The exterior of a white villa is framed by lush green vegetation and tall palm trees, highlighting large windows that allow for plenty of natural light. A balcony extends from the upper level, providing an inviting space to enjoy the surrounding tropical landscape.
Home in Cruz Bay
4.96 out of 5 average rating, 176 reviews

BIG WATERFRONT VILLA WALK SHOPPING & RESTAURANTS

MichaelRating, 5 stars1 week ago
Jon is a wonderful host. We have stayed there multiple times and are always pleased and amazed at the house. So much room, and the kitchen and living area are incredible to hang out in. Looking out of the house through the sliding doors to the bay cannot be accurately described. Great location for a direct walk to downtown Cruz Bay and all restaurants. You have to stay here!
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
4.82 out of 5 average rating, 261 reviews

Privacy. Private Pool Villa@Sapphire. Generator.

DavidRating, 5 stars2 weeks ago
Chris was extremely responsive and answered all of our questions. She also gave us local recommendations and had a cooler and beach chairs available for us to take to the local beaches.
Guest favorite
A serene beach scene features soft, golden sand meeting clear, calm waters under a blue sky adorned with fluffy white clouds. A solitary figure walks along the shoreline, with lush green hills visible in the background, creating a tranquil atmosphere.
Home in Northside
4.82 out of 5 average rating, 194 reviews

Your Own Whole House Beach central 3 KNG Beds AC

AmandaRating, 5 stars2 weeks ago
Just wow!!! We’ve been coming to the islands for about 30 years, mostly staying in St. John… but the views from this villa were the best we have ever had! The villa was just extremely practical and homey! The king beds and cold AC helped us to recover from long days of hikes, snorkels, beaches, and shopping! The decor was so nice and we loved the live plants and orchids! We enjoyed the huge tv as we watched the college World Series in the evenings. The breezes through the villa were very relaxing! We will plan to come again! Thanks Michael for being so helpful, attentive, and quick to respond!
Superhost
A vibrant view from the balcony showcases a lush landscape with bright red flowers in the foreground, contrasting with the turquoise waters of the Caribbean Sea. The scene includes gentle waves lapping at the sandy shoreline and distant green hills rising against a clear blue sky.
Condo in East End
4.77 out of 5 average rating, 113 reviews

Sapphire Beach Resort 1BR Family 1

VanessaRating, 5 stars3 weeks ago
Amazing place to stay !!
Superhost
An inviting common area features an eclectic mix of colorful furniture and artwork. Various seating options, including plush sofas and dining chairs, surround a central wooden coffee table. Large windows offer views of the surrounding greenery, enhancing the open and airy atmosphere.
Place to stay in Water Island
4.82 out of 5 average rating, 115 reviews

Bohemian Paradise Eco Retreat cottages

RenottaRating, 5 stars14 months ago
Wanted a place to take our family and extended family of friends on a vacation they would always remember. This absolutely was that and more. Kids were in awe and so were we. Things we did include going to honeymoon bay multiple x to enjoy the beach, eat and have a few adult beverages. Went to mainland to shop & explore. Ingrid made our stay so much the better w her amazing energy. The massages from her were best I've ever had. Kids had a drum circle night and that was amazing. Our hosts son took us out on his sail boat, super exciting afternoon. The creatures at 4 elements were a fun part of trip. Hermit crabs. Turtles, lizards and cool sounding frogs. My number one recommendation would be to make sure you rent a golf cart before arrival. The walking up hills was likely good for me but I didn't like it 😂. I believe they book up quick so rent golf cart before you arrive. The property is so amazingly beautiful so worth going. Hope we can make it back another year.
Superhost
A bright living space features a light-colored sofa paired with two wooden armchairs, centered around a glass coffee table. Above, the ceiling showcases rich wood paneling. In the background, an open kitchen is visible, complemented by a dining area with bar stools.
Villa in Cruz Bay
4.75 out of 5 average rating, 4 reviews

Starfruit Villa

NateRating, 5 stars25 months ago
This place was awesome. Beautiful views of Cruz Bay and the surrounding islands (for some reason they don’t have any pics of the views in the posting, which they should update!). Very short 5 min drive to the grocery store and all the restaurants and bars downtown. Very short drive to all the incredible north shore beaches. Pool is pretty small but the views from the pool area were great.
Superhost
A private pool is highlighted in the foreground, with steps leading into the water. A spacious deck offers lounge chairs and a shaded dining area under a pergola. Clear blue skies and distant islands create a stunning coastal backdrop.
Home in Cruz Bay
4.87 out of 5 average rating, 87 reviews

Incredible views Mar de Amores. Full Generator

LucasRating, 5 stars1 week ago
Staying at Mar de Amores was an absolute delight. The villa's panoramic ocean views paired with a pool and full-house generator made for total island bliss. Check-in was clear and quick, and the home was spotless and comfortable. Things appeared to be updated and well kept, had no issues. Perfect for families, couples or anyone seeking seclusion just minutes from downtown Cruz Bay—this hidden gem is a St. John must!

Family-friendly home rentals with a pool

Superhost
A saltwater infinity pool is framed by six white lounge chairs, inviting relaxation under the sky. Lush greenery and vibrant flowers surround the space, while sweeping views of the ocean and distant islands create a serene backdrop.
Townhouse in Cruz Bay
4.97 out of 5 average rating, 152 reviews

Ocean Views, Pool, Walk2Town, Backup Generator!

GeorgeRating, 5 stars2 months ago
We has a wonderful 5 day stay in this house located within 10 min walk of downtown Cruz Bay. the place had great views, excellent amenities, pool, and well located. the host,David, was super and very accessibpe and friendly with good suggestions. we would definitely stay again.
Guest favorite
The image captures a private pool area surrounded by lush tropical vegetation. A charming bungalow is visible, with large windows and an inviting outdoor seating area. The pool is bordered by tan tiles, and colorful flowers enhance the vibrant greenery of the setting.
Home in Coral Bay
4.99 out of 5 average rating, 70 reviews

Casa Tua - Saint John

EllenRating, 5 stars1 month ago
We were pleasantly surprised at how quiet and private this home was considering its proximity to restaurants and the main thoroughfare in Coral Bay! It was so convenient for us to get to all the beaches we love to snorkel at AND the very best dinners were at Sharky’s right outside our front gate!! So we did not have to drive to dinner most nights!! We could walk to Crabby’s, practically next door for snorkel rentals. There is also a small market right behind Crabby’s. Any questions we had were answered almost immediately as Jose was living on the premises. We only saw him when we needed help with something. Only concern for Seniors is the winding stairwell to go upstairs to bedrooms and main bathroom. Fortunately, there is a first floor bathroom and shower we also really appreciated being Seniors ourselves!! We LOVED the screened porch surrounding the home and the small pool was refreshing after a snorkel. There is a hose for cleaning sand off everything by the pool.
Superhost
A serene pool area is surrounded by lush tropical greenery and colorful flowers. Several lounge chairs are positioned on the wooden deck, and a few round tables are available for seating nearby. The inviting pool offers a clear view of the calm water beneath the bright sky.
Condo in Cruz Bay
4.83 out of 5 average rating, 77 reviews

1 mile to town, comfortable, steps from the pool.

KsenyaRating, 5 stars3 weeks ago
That was our another great stay at Andrea 's place!!! We enjoyed it very much. Andrea and her family is a fantastic host!
Condo in St. Thomas 00802, USVI
4.79 out of 5 average rating, 182 reviews

Paradise @ Sapphire-WIFI-No Excess Owner Fees #312

StephanieRating, 5 stars2 weeks ago
Lourdes place was just a short walk to the beach. She was always responsive and helped us with everything we asked. Very close to beach restaurants and bar. I would stay here again. Thank you Lourdes for making our stay so easy and seamless.
Superhost
A private deck features a small pool surrounded by comfortable lounge chairs, inviting relaxation. Lush greenery adds natural beauty, while expansive views of the hillside and cloudy sky enhance the serene environment.
Villa in Coral Bay
4.7 out of 5 average rating, 10 reviews

Villa La Mer

ChrisRating, 5 stars6 months ago
Emma’s via is fantastic - beautiful views, amenities, and privacy. Our extended family visited and the pod-style setup worked perfectly to provide ample space. As for the location, we love Coral Bay’s balance of natural beauty, leisurely pace, and east / north end access. Some of the easiest, most efficient check in / out procedures I’ve encountered - very impressed. As mentioned in other reviews, make sure you’re comfortable on steep, narrow roads and have a suitable rental for the terrain. Amazing place - excited to get back!
Superhost
A private pool is framed by a spacious deck, offering expansive views of the ocean and distant islands. Lush greenery surrounds the area, complemented by a clear blue sky adorned with fluffy white clouds.
Home in St Thomas
4.8 out of 5 average rating, 50 reviews

Eden View Book you winter and spring dates!

MikeRating, 5 stars1 month ago
absolutely beautiful property! incredible views. House was well equipped in extremely comfortable. The pool was lovely and perfectly maintained. although we didn't cook in the kitchen this trip the kitchen had everything you could ever need. Both hosts we're extremely proactive and helpful. 10/10 would highly recommend and will definitely be staying here again.
Superhost
A pool deck is shown overlooking lush green hills with scattered residential buildings. The pool features a sturdy handrail and is bordered by multiple lounge chairs. Bright clouds fill the blue sky, enhancing the inviting atmosphere of the space.
Condo in Cruz Bay
4.89 out of 5 average rating, 56 reviews

Tropical Breeze: Comfortable Downtown Vacationing

KimRating, 5 stars4 weeks ago
Tropical Breeze at Battery Hill. What a wonderful place. The condo was spacious and clean. Plenty of supplies and the kitchen, although we didn't really use it, was well-stocked. The view is gorgeous. Our hosts were incredibly responsive and all directions were very easy to understand. I would highly recommend this place based on spaciousness, cleanliness, responsiveness and the amazing views.
Top guest favorite
A covered veranda features comfortable seating with light blue cushions and a wooden coffee table. Lush greenery is visible in the background alongside palm trees, enhancing the view of the vibrant water beyond. Ceiling fans provide an airy feel to the space.
Condo in Cruz Bay
4.95 out of 5 average rating, 20 reviews

Bravo @Serendip Vacation Condos

MikeRating, 5 stars1 week ago
Check in was very easy. When we opened the door, the place was immaculate. The view is incredible. Our 12 year old son enjoyed his area where he had the sleeper sofa and some privacy curtains. Bathroom was very nice. Kitchen was spotless and had everything you need. The veranda was the place to be for morning coffee and evening drinks. We also used the pool several times and thoroughly enjoyed that as well. Matt is a great host. Friendly to talk to as well as responds right away when we texted him. We had a great vacation and highly recommend the Bravo unit as part of the Serendip condos.

Quick stats about vacation rentals that are family-friendly in Anna's Retreat

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ551 before taxes and fees

  • Total number of reviews

    250 reviews

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

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