
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

Beachside Escape 3 BDRM at Cowpet Bay East
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.

Sunkissed Serenity -Island Chic Home at Cowpet Bay
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.

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!

Villa Amour , Romantic , Art lover's paradise
Happy with stay. View was spectacular. 100% need a Jeep or SUV to get to the house. Wonderful experience. Would go back.

GRANDE BAY 1 BR; SPECTACULAR VIEWS
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 .

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

3-Bed St. Thomas Getaway on the Bay
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.

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!
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!

Mar Brisa
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 .

Privacy. Private Pool Villa@Sapphire. Generator.
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!

PANOrama! Standalone Home 3 KNG Beds Super Central
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.

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.

Starfruit Villa
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.

Dog-Friendly 2BR in the Sky, Stunning Ocean Views
Gorgeous views and great island feel nestled into the hill! Barb was super accommodating and helpful, definitely and 5 star stay!

5 minute walk to Cruz Bay, Quiet Studio Apartment.
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

Sea View Deluxe Suite in St. Thomas
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!

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.

Beach, Bed and Beyond! Walk out to beach
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!!

Stunning Beachfront Condo w/ Marina & Island Views
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!

Sapphire Outlook Villa: Oceanfront Sapphire Beach
Alexander was a very good host. He was responsive and accommodating. The place was exactly as advertised and in great shape. Would stay again.

Beautiful view of Magen's Bay Beach
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

Villa in Paradise with Private Pool and Generator
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.

Villa Solare -sunsets, private pool
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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- Flamenco Beach
- Honeymoon Beach
- Magens Bay Beach
- Limetree Beach
- Mosquito Bay Beach
- Oppenheimer Beach
- Coki Beach
- Cane Garden Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Peter Bay Beach
- Morningstar Beach
- Gibney Beach
- Pelican Cove Beach
- Josiah's Bay
- Playa Sun Bay
- Maho Bay Beach
- Caneel Bay Beach
- Playa el Convento
- Salt River Beach
- Grapetree Beach
- Sugar Beach
- Hull Bay Beach
- Mandahl Bay Beach