Holiday rentals with a pool in Anna's Retreat

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Popular amenities for Anna's Retreat rentals with a pool

House rentals with a pool

Top guest favourite
Home in NorthSide
5 out of 5 average rating, 46 reviews

Heated Pool, OceanView, Generator, Local Discounts

MeganRating, 5 stars4 days ago
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!
Guest favourite
Home in Northside
4.95 out of 5 average rating, 57 reviews

Private Saltwater Poolside Cottage w/View and Gate

JerryRating, 5 stars5 days ago
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.
Superhost
Home in St. Thomas
5 out of 5 average rating, 31 reviews

Secluded Villa with Ocean Views

IsabelleRating, 5 stars1 month ago
CalypsoBlu was an absolutely beautiful home and Justin and his team were fantastic! The home was clean and complete with all the listed amenities. The team was helpful and responsive, giving us plenty of information and great recommendations before we even arrived on the USVI! They were also extremely quick to respond when we had questions during the trip. We cannot recommend this place more!
Guest favourite
Home in Northside
5 out of 5 average rating, 33 reviews

Oceanfront Private Caribbean Resort!

MargaretRating, 5 stars4 days ago
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!
Guest favourite
Home in Northside
4.95 out of 5 average rating, 107 reviews

Change Your Perspective at Villa Point of View

GinaRating, 5 stars1 month ago
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.
Superhost
Home in Northside
4.82 out of 5 average rating, 114 reviews

Texas Embassy

KunguRating, 5 stars2 months ago
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.
Top guest favourite
Home in Cruz Bay
4.98 out of 5 average rating, 50 reviews

Caribbean Cottage Near the Sea

EmilyRating, 5 stars3 weeks ago
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!!
Guest favourite
Home in Southside
5 out of 5 average rating, 8 reviews

Sea Sun VIlla 3/2 Villa, walk to Limetree Resort

JeffRating, 5 stars1 month ago
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.

Apartment rentals with a pool

Guest favourite
Apartment in East End
4.91 out of 5 average rating, 186 reviews

Somewhere in the Sun

TeresaRating, 5 stars1 month ago
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
Top guest favourite
Apartment in East End
4.98 out of 5 average rating, 199 reviews

Stunning Ocean View w/Balcony~Shades of Sapphire~

MatthewRating, 5 stars1 week ago
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!
Top guest favourite
Apartment in East End
5 out of 5 average rating, 181 reviews

"H2Oh What a Beach!" condo: Walk-out Beach Access!

DianeRating, 5 stars1 month ago
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!
Guest favourite
Apartment in East End
4.95 out of 5 average rating, 128 reviews

Sea-N-Dipity 1 by the Sea @ Sapphire Resort

LukeRating, 5 stars2 days ago
Scott’s place was fantastic. Looked just like the photos and awesome location. Would highly recommend.
Guest favourite
Apartment in Southside
4.95 out of 5 average rating, 102 reviews

Sea Dreams at Regatta Point Villas

JohanaRating, 5 stars4 weeks ago
Excellent stay in St. Thomas! I had an amazing experience at the Airbnb hosted by Caribbean Properties. Everything was super clean and well-maintained. The kitchen had all the utensils I needed to cook, which was a big plus. They also provided everything you’d need for the beach, which made my stay even more enjoyable. You can really see the attention to detail. I totally recommend this place and would love to come back!
Guest favourite
Apartment in East End
4.84 out of 5 average rating, 222 reviews

Villa in Paradise with Private Pool and Generator

ErickRating, 5 stars1 week ago
LISTEN TO YOUR HOST! Laverne strongly recommended we get a rental car — my wife and I love to walk so we didn’t get one — we will not go back to St. Thomas unless we rent a car! Now the space: the pictures don’t do it justice the bedroom, pool area, bathroom, and living room are larger than perceived in photos and the kitchen has ample room for one cook at a time, two if you’re skilled! All areas of the accommodation were spotless and insectless inside! The bed is better than ours at home and we’re still thinking about that one of a kind bathroom and the pool lights! I swear the walls are sound proof, there were families in either side of us with kids and we never heard a peep inside. The property grounds and walkways are well maintained Laverne is a master of instructions. We never had to double text, ask what was meant, clarify our end, it was smoother than we had even hoped and for that we would recommend this place to anyone, especially for their honeymoon like we did!
Superhost
Apartment in East End
4.82 out of 5 average rating, 130 reviews

Luxury 1/1 Oceanfront @ Sapphire Beach Resort

KarolineRating, 5 stars3 weeks ago
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!!
Guest favourite
Apartment in Sapphire Beach
4.96 out of 5 average rating, 197 reviews

Salt Life at Sapphire Beach

CarolynnRating, 5 stars1 week ago
Great place to stay! Very convenient if you want to explore St. John too! John was responsive and kind. We really appreciated the recommendations and insights into the area prior to our stay. We would love to stay here again soon!

Quick stats about holiday rentals with a pool in Anna's Retreat

  • Total rentals

    70 properties

  • Nightly prices starting at

    $167 SGD 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

  • Wifi availability

    70 properties include access to wifi

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