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

BEAUTIFUL GRANDE BAY STUDIO CONDO W/ GREAT VIEWS
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.

Cottage w/Awesome View, Hot Tub, Solar, sleep 2-4
Cynthia and her team were amazing. From the moment we booked until we left, the communication was prompt and helpful. The place is Heaven on Earth! The views are amazing and very private. There are gorgeous paths on the property with exotic plants and wildlife. The hosts have everything you will need, including aloe for sunburns, beach chairs, snorkeling gear, towels, coolers, etc. This is probably the nicest and most well appointed rental we have stayed in. The location is quiet and only a short drive to restaurants, the market, marina, beaches and hikes. However, being at the far end of the island, everything is scaled down and there are fewer people. We found uninhabited beaches and some of the best hiking ever. If you don't like crowds, this is the place for you. Highly recommend.

Charming One Bed Cottage with Hot Tub and Views!
This place was AMAZING!!! The views were spectacular. Perfectly suited for a couple wanting to enjoy a romantic getaway on a beautiful island.

Sunkissed Serenity -Island Chic Home at Cowpet Bay
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!

Amazing Beachfront Condo, Elysian Resort
Great condo in a gorgeous resort! Nancy was very responsive and easy to work with.

Resort on the Beach! Enchance cleaning.Great area!
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!

Romantic Cottage - Stunning Ocean Views, Hot tub.
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!

Leap of Faith at Cowpet Bay East
Great week at Leap of Faith. Everything was immaculate, and Amy was a terrific and very responsive host. Helped us to book a catamaran excursion that turned out to be terrific, very helpful with insight about local places. Would highly recommend everything about it.
Family- and pet-friendly home rentals

Breezy Beautiful Northside Cottage
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!

Privacy. Private Pool Villa@Sapphire. Generator.
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.

Your Own Whole House Beach central 3 KNG Beds AC
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!

Sapphire Beach Resort 1BR Family 1
Amazing place to stay !!

Bohemian Paradise Eco Retreat cottages
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.

Seagrape Villa
This property has everything we expected and more. It is more spacious than what the pictures show. Not only the bedrooms are big, but huge bathrooms and closets too. Family had good time. Highly recommended.

Incredible views Mar de Amores. Full Generator
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!

Dog-Friendly 2BR in the Sky, Stunning Ocean Views
I loved my stay here, the space was beautiful, clean and has sm character. Despite having AC the home stayed cool with the many windows and fans. The driver that Bg recommends got us everywhere we needed to go and always prompt. Overall would love to go back to ST. Thomas just to stay at this Airbnb so peaceful and quiet ugh a dream!!
Family-friendly home rentals with a pool

Ocean Views, Pool, Walk2Town, Backup Generator!
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.

Casa Tua St John
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.

1 mile to town, comfortable, steps from the pool.
That was our another great stay at Andrea 's place!!! We enjoyed it very much. Andrea and her family is a fantastic host!

Dream House
The home was very clean and beautiful. It’s located on the quieter side of the island, which is nice but you will have a drive to get to places but honestly, you’ll have a drive no matter where you’re located on the island, especially if you want to check out different beaches. I highly recommend this property for couples and people with older children. If my children had been younger, I wouldn’t have liked it because you had to go outside to get to two of the bedrooms.

Stunning View, Magens Bay, Pool, Amazing Villa!
This home was exactly what we needed for our group of seven (five adults and two children). Everyone had their own space and we were able to come together in the large living room and cook several meals together. The home was as beautiful as it is in the pictures and the views are amazing. The home had all of the amenities that were described and then some; there are games and toys for the kids too. We were informed that the oven was non-functional at the time we arrived and they were in the process of fixing it but this was not a problem for our stay. There is a remote-operated gate at the end of the driveway that made the place feel so secure. There is a home binder that describes many things we needed to know for our stay; I recommend reading this at the start of your stay. Marina, our host, communicated with us before and upon our arrival. I would stay here again!

Eden View Book you winter and spring dates!
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.

Condo Del Sol
Absolutely gorgeous view! From bed I could see the marina and the water. So close to red hook. 5 dollar taxi to town and back. 100 percent would stay again! And he let me check in early! Obssesed! Walking distance from Sapphire

Coral @Serendip Vacation Condos
Beautiful location and property! We felt right at home. Nice pool and gardens. Peaches, the cat was very friendly. Matt was awesome. Will be back next year.
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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- Flamenco Beach
- Honeymoon Beach
- Magens Bay Beach
- Limetree Beach
- Mosquito Bay Beach
- Oppenheimer Beach
- Coki Beach
- Cane Garden Beach
- Chocolate Hole
- Cinnamon Bay Beach
- Cane Bay Beach
- Peter Bay Beach
- Gibney Beach
- Pelican Cove Beach
- Josiah's Bay
- Playa Sun Bay
- Caneel Bay Beach
- Maho Bay Beach
- Playa el Convento
- Salt River Beach
- Virgin Islands National Park
- Oil Nut Bay
- Playa Puerto Real
- Grapetree Beach