
Holiday rentals with a pool in Anna's Retreat
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Top-rated rentals with a pool in Anna's Retreat
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Anna's Retreat rentals with a pool
House rentals with a pool

Heated Pool, OceanView, Generator, Local Discounts
Wonderful place to stay! It felt private and safe. It was a little challenging to get to, but as with anywhere on the island, without the adventure you don’t get the views! Stacie had exceptional communication, including a guide for nearby beaches/restaurants/grocery stores. Very clean. What stood out most were the “extra” amenities. We made use of the beach chairs, beach towels, a pair of snorkeling fins, etc., even the first aid kit! Would highly recommend!

Private Saltwater Poolside Cottage w/View and Gate
The view and pool are amazing! The inside was nicely done and well equipped. If you’re looking for something with a view and pool and not far from town, this is a great option.

Oceanfront Private Caribbean Resort!
Sea La Vie was the perfect St. Thomas escape. The space is clean, stylish, and peaceful, with a fully stocked kitchen that made cooking at home a breeze. The pool area was a highlight – quiet, with plenty of lounge chairs and an incredible ocean view that we never got tired of. The hosts were welcoming and responsive, and the location made it easy to explore beaches, restaurants, and local spots. Whether relaxing by the pool or enjoying dinner on the deck, every moment felt like paradise. Highly recommend!

Change Your Perspective at Villa Point of View
Dionne’s spot was awesome. It was close proximity to any area on the island and easy to find. The view of the harbor was absolutely out of this world and we enjoyed watching storms roll in. The kitchen is well equipped and each room is stocked with towels. Overall, we loved our stay and would happily return to Dionne’s! The symphony of frogs singing each night was the icing on the cake.

Caribbean Poolside Cottage
Michael and Jenny were above and beyond the best hosts we have had from AirBnB. From the beautiful location, amazing recommendations, and easy going demeanor you couldn’t ask for more. Everything about the description is accurate and you can expect the view to be even better in person. They also provided a detailed cottage guide that clearly stated guest expectations and provided amazing recommendations for beaches/restaurants/groceries/etc.

Texas Embassy
Great view! very spacious! We enjoyed our stay & would come back again. It can be a little difficult to locate even with instructions, but once located no additional issues getting into the house. You should definitely rent an SUV or Jeep to get around the island and to get up the driveway at the property. Host was very accommodating as we arrived earlier than expected. The local co-host (Donovan) provided some local food options & less busy beach options.

Caribbean Cottage Near the Sea
My husband and I spent our honeymoon at St. John and choosing Ramona and Chris’s place was absolutely perfect. Chris met us when we got our rental car and led us to the Airbnb which was so kind and helpful. He gave us a ton of local recommendations and answered any questions we had throughout the week. The views are absolutely breathtaking and are hard to fully capture on their listing pictures! The AC worked wonderfully and the outdoor shower made things feel extra tropical! The place came with a few cat friends that we thoroughly enjoyed and the stairs were the perfect workout in the morning before the beach. We hope to come back to St. John in the near future and will most definitely be back here if it is just the two of us! Thanks for making our trip so memorable with a wonderful home for the week!!

Sea Sun VIlla 3/2 Villa, walk to Limetree Resort
This place was absolutely amazing. From the moment we arrived to the moment we left. We arrived early and we were allowed to check in early & greeted at the home with a tour from the host. The view was breathtaking! The pool was a huge addition to our stay. Would definitely recommend this location if you are visiting St. Thomas with family or friends. Everything was close by food, beaches, stores etc.
Condo rentals with a pool

Somewhere in the Sun
Loved the place and the location! Met some great people around the apartment complex. We also found sapphire beach to be the best for us on the island

Stunning Ocean View w/Balcony~Shades of Sapphire~
Deb and Rob were gracious hosts who described their apartment accurately in their listing. They were proactive in their communication, check-in was easy, the apartment was perfect for two, and we look forward to returning next year! The location was a five-minute walk from Sapphire Beach and the Marina, where we took Deb and Rob up on their offer to go sailing and snorkeling - worth the additional booking. Thank you again for allowing us to visit your home!

"H2Oh What a Beach!" condo: Walk-out Beach Access!
Our stay at Darryl & Deb's couldn't have been better. From the minute we booked our trip, they were in communication and provided answers for anything we inquired about. On the day of our arrival, we found everything to be as described and never had a complaint for the 10 days we stayed. The location of their condo is prime, with the patio being just steps to the water. It is also close - but not too close - to the bar and several options for eating, as well as the area where live music or a DJ is provided on weekends. We enjoyed a wonderful and relaxing 10 days and really can't think of anything that we would improve upon. Thank you Darryl and Deb for your hospitality. We will be back!

Sea-N-Dipity 1 by the Sea @ Sapphire Resort
Scott’s place was fantastic. Looked just like the photos and awesome location. Would highly recommend.

Sail Away II-WOW Beachfront to Paradise Remodeled
We had a great time staying at sail away on sapphire beach. Great walkout little condo with easy access to all of St. Thomas. Super close to Red hook, 20 minutes to magens bay and minutes to various other beaches. We took the car ferry a couple times to St. John and that is super close as well. We met lots of nice people in the same complex. The pool is right outside the condo and watching the sunrises every morning was a treat. We stayed with our son who slept on the pullout and we were all comfortable.

Luxury 1/1 Oceanfront @ Sapphire Beach Resort
Amazing stay at Ana’s place! Walking distance to the beach and all the restaurants sapphire beach has to offer. Would absolutely come back!! Ana was so responsive with recommendations and help when needed. Thank you!!

You & Me By The Sea
I’m giving a real review Shannon is absolutely lovely she was far more than accommodating for my trip I had arranged things for my girlfriend prior to arriving and she was very helpful flight got delayed so we got to check out later and was perfectly cool about it she’s truly an angel and made this trip amazing for us I really appreciate her and highly recommend anybody to book her truly phenomenal and I definitely plan on coming back if I can give 10 stars I would

Sapphire Village Resort Getaway
Matt is a great host. very responsive, place is clean and good Location. This was our 2nd time staying at Matt’s, definitely will be back.
Quick stats about holiday rentals with a pool in Anna's Retreat
Total rentals
70 properties
Nightly prices starting at
$217 NZD before taxes and fees
Total number of reviews
310 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wi-Fi availability
70 properties include access to Wi-Fi
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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