Family-friendly vacation rentals in Anna's Retreat

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Popular amenities for Anna's Retreat family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Aerial view of a serene beach with clear turquoise waters and gentle waves lapping at the shore. Palm trees dot the sandy beach, while colorful lounge chairs are arranged under shaded areas. A few boats float nearby, with a backdrop of cozy condos lining the hillside.
Condo in East End
4.86 out of 5 average rating, 22 reviews

Beachside Escape 3 BDRM at Cowpet Bay East

CharlesRating, 5 stars6 months ago
This condo was perfect for a family vacation. Amy was a great communicator leading up to the trip...she was proactive about travel instructions, check-in process, and even offered to help coordinate local activities. The space was clean and as-described. It was a very quick walk to the beach and pool, making it easy for our group to come up/down at our own pace. The condo was a quick drive (5 min) to the Red Hook area, where there were plenty of restaurants to check out. Overall, it was a great experience and would definitely recommend.
Guest favorite
The living area features comfortable sofas adorned with colorful cushions, creating a vibrant atmosphere. A dark coffee table sits centrally, complemented by a neutral rug. Exposed wooden beams line the ceiling, enhancing the spaciousness of the room, which opens into a dining area.
Condo in East End
4.99 out of 5 average rating, 73 reviews

Sunkissed Serenity -Island Chic Home at Cowpet Bay

JarodRating, 5 stars1 month ago
Beautiful view, clean condo with nice furniture and decor, walking distance to beautiful beach and pool, beach bar, great restaurant and a lunch restaurant/bar. The drivers Keshri suggests in the welcome package are great, especially the wonderful and amicable "Jeff-I" who took great care of us and could be at the condo in about 10 mins each time needed.
Superhost
A beachside view is offered from a shaded patio, showcasing a sandy shore lined with palm trees. In the distance, colorful buildings and boats are visible on the water. Wooden tables and chairs are arranged on the deck, creating a casual dining atmosphere.
Condo in Saint Thomas
4.67 out of 5 average rating, 3 reviews

Resort on the Beach! Enchance cleaning.Great area!

DonnaRating, 5 stars46 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!
A bathroom is presented with dual sinks set in a wooden vanity, framed by two round mirrors. Colorful artwork is displayed on the walls, complemented by a green tile accent. A glass block shower enclosure is visible, providing a sense of light and openness.
Villa in Northside
5 out of 5 average rating, 16 reviews

Villa Amour , Romantic , Art lover's paradise

MikeRating, 5 stars8 months ago
Happy with stay. View was spectacular. 100% need a Jeep or SUV to get to the house. Wonderful experience. Would go back.
Superhost
A well-appointed bathroom features dual sinks with dark stone countertops and ample natural light. Mirrored cabinets reflect the space. A doorway leads to a cozy bedroom, while plush towels hang neatly on the wall. Warm tones enhance the inviting ambiance throughout the area.
Apartment in Cruz Bay
5 out of 5 average rating, 19 reviews

GRANDE BAY 1 BR; SPECTACULAR VIEWS

ChrisRating, 5 stars2 months ago
We loved this condo. Well appointed kitchen including a dishwasher and all the appliances you could ask for. Washer and dryer were very useful after a day at the beach . Everything was so close that we didn’t feel we needed a car (even tho you get a dedicated parking space). Shared taxis to the beaches are just 5 mins walk away. We appreciated use of the included beach chairs which were easy to carry on trips .
A spacious living room features large windows allowing ample natural light and offering views of the surrounding greenery. Comfortable seating is provided by patterned sofas and a wicker coffee table. The decor includes tropical-themed cushions and a warm color palette, creating a relaxing environment.
Cottage in Coral Bay
5 out of 5 average rating, 6 reviews

Cottage w/Awesome View, Hot Tub, Solar, sleep 4-6+

JulieRating, 5 stars2 weeks ago
Our stay at Stonehenge Cottage checked all the boxes - perfect location, beautiful surroundings, plenty of room for 5 adults, comfortable beds, and lots of amenities. The place is close to restaurants in Cruz Bay and there are 3 markets to pick up groceries and fresh fish for cooking at home. It is also close to the hiking trails and beaches on the south side of the island which are less populated and provide great snorkeling.
A serene beach scene is highlighted by gentle waves lapping against the sandy shore. Palm trees frame the view, while anchored boats can be seen in the clear turquoise water. Green hills and white buildings provide a picturesque backdrop to this coastal retreat.
Condo in East End
4.68 out of 5 average rating, 34 reviews

3-Bed St. Thomas Getaway on the Bay

AndyRating, 5 stars14 months ago
a little tough to find in the rain and dark, but the location is excellent and it's the end unit on the beach next to the restaurant. the convenience and proximity to the east end goings on was excellent. theres also a bunch of snorkeling equipment, bug spray, sunscreen , etc thats left from other guests. again, super handy.
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, 75 reviews

Romantic Cottage - Stunning Ocean Views, Hot tub.

tiffanyRating, 5 stars2 days 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!

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, 315 reviews

Breezy Beautiful Northside Cottage

JoanRating, 5 stars1 month 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
A welcoming mosaic sign stands against a natural backdrop of lush greenery and desert plants. Cacti and vibrant foliage surround rocky terrain, under a bright blue sky with scattered clouds, creating a serene outdoor setting.
Guest suite in Water Island
4.88 out of 5 average rating, 113 reviews

Mar Brisa

Shana TinoRating, 5 stars3 weeks ago
We needed a get away from busy life and found Water Island and Ray and Cheri’s place to be perfect. Can walk to Honeymoon beach , golf Cart around the island ( rent at the docks ) food at the two places that serve is excellent people are very nice and easy to get to know. I didn’t hear one police siren or ambulance all week and that’s beautiful. There is not much congestion in people , it’s just very peaceful and we will be going back for sure .
The living area features a rattan sofa adorned with cushions, complemented by a wooden armchair. A low coffee table rests on a vibrant area rug, while a framed underwater artwork adds color to the purple walls. A lamp softly illuminates the space, and a television is positioned nearby.
Condo in Smith Bay
4.82 out of 5 average rating, 260 reviews

Privacy. Private Pool Villa@Sapphire. Generator.

KellyRating, 5 stars1 month ago
I loved staying here! Private, peacefule, and a pool, short walk to the beach and restaurants. I would defintely stay again, can't wait to go back!
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
4.81 out of 5 average rating, 187 reviews

PANOrama! Standalone Home 3 KNG Beds Super Central

SawyerRating, 5 stars3 weeks ago
This place is 100% where you want to stay if you want a truly peaceful island get away! We enjoyed the open air set up of the property, morning and evening costal mountain winds were phenomenal. (Our April stay, the multiple mini split systems weren’t needed) We were able to watch deer, iguanas and all kinds of birds on the wrap around deck. Which also doubled as a great safe and secure play area for our kids. Mike was very friendly and responded quickly to all of our questions/needs! If you’re looking for a quiet, peaceful island getaway, this property is where you need to stay.
Superhost
Place to stay in Water Island
4.82 out of 5 average rating, 114 reviews

Bohemian Paradise Eco Retreat cottages

RenottaRating, 5 stars12 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
The entrance to the villa community is marked by elegant stone gates, framed by lush greenery and decorative plants. A paved pathway leads into the property, showcasing a peaceful and inviting atmosphere under a bright blue sky.
Villa in Cruz Bay
4.75 out of 5 average rating, 4 reviews

Starfruit Villa

NateRating, 5 stars23 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 round dining table is set with decorative candles, surrounded by four chairs. Floor-to-ceiling windows showcase stunning views of the ocean. Light-filled space creates an inviting atmosphere, with a comfortable seating area visible in the background.
Apartment in Southside
4.85 out of 5 average rating, 27 reviews

Dog-Friendly 2BR in the Sky, Stunning Ocean Views

DarianRating, 5 stars9 months ago
Gorgeous views and great island feel nestled into the hill! Barb was super accommodating and helpful, definitely and 5 star stay!
A cozy sleeping area features a colorful quilt adorned with marine patterns over a spacious bed. A small fan and window-mounted air conditioning unit are visible, alongside a table with flowers. Natural light enters through a window with sheer curtains, contributing to a bright atmosphere.
Apartment in Cruz Bay
4.76 out of 5 average rating, 205 reviews

5 minute walk to Cruz Bay, Quiet Studio Apartment.

CalebRating, 5 stars3 weeks ago
This was our fifth year on the island and first stay with Steven’s property. Steven’s description of the apartment was accurate and detailed. Although small, the space was very homey and comfortable. Steven was very responsive and checked in with us throughout our stay to make sure we were happy and had everything we needed! Lots of recommendations were made and the apartment is the perfect walkable distance to Cruz Bay for all dining and night life experiences you could want! The apartment was clean and well stocked for the needs of a week long stay! Overall, my wife and I were very satisfied with the accommodations and enjoyed our stay! I highly recommend booking with Steven!

Family-friendly home rentals with a pool

A private swimming pool is framed by a tiled patio, featuring a round dining table with chairs beneath an umbrella. Lush potted plants enhance the area, while the backdrop reveals a multi-level building and clear blue sky.
Apartment in Charlotte Amalie
4.25 out of 5 average rating, 4 reviews

Sea View Deluxe Suite in St. Thomas

MegRating, 5 stars48 months ago
the view is just lovely! I recommend having a vehicle if staying here , as it is up a steep winding hill and it's not necessarilysafe to walk it. Has ac, kitchen amenities, coffee, a vending machine outside and a cute little pool. I enjoyed my stay very much!
Guest favorite
The open-concept living area displays modern furnishings, including a light sofa and a pair of matching armchairs adorned with patterned cushions. A dining table for six is positioned nearby, with a full kitchen equipped with wooden cabinets and stainless-steel appliances visible in the background.
Townhouse in Cruz Bay
4.97 out of 5 average rating, 151 reviews

Ocean Views, Pool, Walk2Town, Backup Generator!

GeorgeRating, 5 stars5 days 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
A patio area features a table surrounded by four chairs, offering direct views of the sandy beach and turquoise water. Lush greenery frames the outdoor space, contributing to a serene atmosphere. The scene is bright, reflecting the vibrant coastal surroundings.
Condo in East End
4.87 out of 5 average rating, 38 reviews

Beach, Bed and Beyond! Walk out to beach

ColleenRating, 5 stars1 week ago
What a stellar location! Walking out the door onto the sand was wonderful. There are food & drink options nearby, as well as the marina. Well stocked with Moe’s market close to get anything else you may need. The host was responsive to questions. I highly recommend this fabulous locale!!
Guest favorite
Condo in East End
4.86 out of 5 average rating, 65 reviews

Stunning Beachfront Condo w/ Marina & Island Views

PhyliciaRating, 5 stars2 weeks ago
Shellie’s place was just as it was described! It was in walking distance to Sapphire beach, there was a restaurant in the same building, and it came with a lot of amenities that we were looking for. Her place was also close to Red Hook, where we were able to catch a ferry to St John’s for the day. Would highly recommend!
Superhost
A shaded balcony offers a view of Sapphire Beach, showing palm trees swaying along the shoreline. A white table is set with two coffee mugs, and the inviting blue waters of the Caribbean are visible in the background.
Condo in East End
4.82 out of 5 average rating, 119 reviews

Sapphire Outlook Villa: Oceanfront Sapphire Beach

SeanRating, 5 stars4 days ago
Alexander was a very good host. He was responsive and accommodating. The place was exactly as advertised and in great shape. Would stay again.
Guest favorite
Apartment in Charlotte Amalie
4.93 out of 5 average rating, 284 reviews

Beautiful view of Magen's Bay Beach

DonnaRating, 5 stars2 weeks ago
Myrla was the very best in helping us during our wonderful stay at her place. The view is gorgeous. The studio was comfortable. We went to many of her recommendations and were quite pleased. If you are coming to Magen’s Bay, she is the best
Superhost
A pathway lined with vibrant flowers leads to a villa entrance, surrounded by lush tropical foliage. Sunlight filters through the greenery, enhancing the serene and secluded atmosphere of the garden area.
Condo in East End
4.83 out of 5 average rating, 218 reviews

Villa in Paradise with Private Pool and Generator

JenniferRating, 5 stars1 week ago
This place was gorgeous!! Lots of wildlife just in the area, saw hermit crabs, lizards, chickens, and fish down at the beach. Sapphire beach has lots of restaurants to enjoy, and PANGEA is to die for! With locally sourced food, we ate there almost every day during our stay. Our one downfall was not renting a car, which the hosts recommended. BUT there were plenty of taxi options and locals were all very friendly. Loved shopping in downtown Charlotte Amalie, and enjoying the live music at Sapphire beach. Hosts had snorkeling gear delivered to us free of charge as well. The HIGHLIGHT of this property is the private pool and back deck. You could hear your neighbors, but not clear enough to hear their full conversations. Definitely enjoyed floating in the pools in the AM with a book. OVERALL, it was a great trip and would DEFINITELY stay here again. Thank you Kim and Laverne, for the wonderful place. And thank you St. Thomas for letting us enjoy the island life.
A functional bathroom features a stand-up shower separated by a glass block partition. A sink with a mirror above is positioned beside a small toilet, with fresh towels neatly arranged nearby.
Villa in Central
4.93 out of 5 average rating, 14 reviews

Villa Solare -sunsets, private pool

JenniferRating, 5 stars3 weeks ago
Villa Solare was the perfect place for our group. We loved the separation if people wanted to go hang in their own area but plenty of space for us to hang as a group in the main house and patio area. The views are incredible (pictures don't even do it justice!). The pool was fantastic and we loved that it was saltwater. The water temp was perfect. Susan provided PLENTY of amenities (TP, paper towels, spice cabinet stocked, etc) for our 8-day stay. The grill was an excellent feature (we grilled out multiple nights and never ran out of fuel). Highly recommended & hope to stay here again the future!

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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