
Holiday rentals with a pool in Anna's Retreat
Find and book unique homes with a pool on Airbnb
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.
Holiday rentals for every style
Get the amount of space that is right for you
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!!

Honeycomb Hideaway
I highly recommend Kia's place at Mahogany Run South. Everything was perfect. I loved that there is a gate to enter for security. Checkin was easy and convenient with a door code. I didn't have to worry about losing the key. I loved the large space. There was plenty of room and it made my stay feel like I was at home and not living in a box for ten days. The kitchen was great. I was able to make breakfast every morning. I also loved all of the small details here and there. Everything was lovely and felt special. I loved the spacious bedroom. I was able to hang up my clothes and put the others in the drawers. I enjoyed lounging in the living room and watching tv. It was great to have a washer and dryer available. I also absolutely loved having an assigned parking spot. No matter what time I returned my space was mine and I didn't have to go hunting for a place to park. Location, location, location. Being close to Magens Bay and Brook's Bar was the best.
Apartment 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!
Deb & Darryl's condo is quite possibly the very BEST location at Sapphire Beach! Being on the ground floor made access to and from the beach so simple (especially with a kid) and the view is still fantastic from the porch - but the view is even BETTER just steps away on the shore! D&D are extremely thoughtful about what they provide to their guests: a stash of masks, snorkels, fins (even two pairs that would fit a child), beach bags, pool noodles/floats, and ample bath AND beach towels. From the small and large coolers (w/ some ice packs ready for use in the freezer), to the Shout laundry spray, the condo was well stocked with all the essentials! *Check the fridge before going to the store!* The music from the bar/restaurant area next door was noticeable (background "thumping") when outside, but it was not heard when inside the condo with the doors closed. Other than a dinghy rental on St. John, we spent most days hanging out at Sapphire- so beautiful with great waves to play in!

HarborHouse-PRIME OCEANFRONT VILLA SAPPHIRE BEACH
We had an amazing time at Ben and Erica’s property! It was a great location to enjoy the amenities at Sapphire beach and the bars and restaurants in nearby Red Hook. It also provided a great jumping off point for catching a boat charter and enjoying the beauty of St. John. The place was incredibly clean and well stocked and we especially enjoyed the view from the balconies. The only complaint we had is that our party of 5 (listed on the reservation) had a little bit of trouble locating the extra linens for the pull out beds. Other than that tiny hiccup we had the absolute best time at Ben and Erica’s condo and would definitely stay again!

Villa in Paradise with Private Pool and Generator
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!

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!!

Stay in style right on the ocean -Simply the BEST!
Couldn’t have asked for a better stay! The location was PERFECT. The condo was clean and equipped with everything that we needed. The welcome packet that Mike provided was extremely helpful! We will definitely be back!
Quick stats about holiday rentals with a pool in Anna's Retreat
Total rentals
70 properties
Nightly prices starting at
₹11,250 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
Destinations to explore
- Carolina Holiday rentals
- Culebra Holiday rentals
- Saint Thomas Holiday rentals
- Saint Croix Holiday rentals
- Tortola Holiday rentals
- Luquillo Holiday rentals
- Fajardo Holiday rentals
- Palmas del Mar Holiday rentals
- Vieques Holiday rentals
- Condado Beach Holiday rentals
- San Juan Holiday rentals
- Punta Cana Holiday rentals
- Rentals with a washing machine and dryer Anna's Retreat
- Rentals with a hot tub Anna's Retreat
- Rentals with outdoor seating Anna's Retreat
- Rentals with a patio Anna's Retreat
- Rentals with beach access Anna's Retreat
- Fitness-friendly rentals Anna's Retreat
- Family-friendly rentals Anna's Retreat
- Guest house rentals Anna's Retreat
- Apartment rentals Anna's Retreat
- Flat rentals Anna's Retreat
- Rentals with pools U.S. Virgin Islands
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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