
Holiday rentals with a pool in Anna's Retreat
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Top-rated 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

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!

Secluded Villa with Ocean Views
Justins place was everything we wanted and more for our trip to St. Thomas. As soon as you walk in you enter into a gorgeous view of the island. Which you can see from virtually anywhere on the property. The place was very clean, private, and had all the amenities we needed for our stay. Justin provided amazing recommendations which we utilized almost daily especially the food choices. Justin and his team were very communicative and helpful throughout the stay. Overall this place is incredible and I highly recommend it for anyone coming to visit St. Thomas.

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!

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!!

Island Daze - Amazing Views
This is a beautiful retreat - the views, the condo, all refreshing and relaxing. We booked at the last minute and thoroughly enjoyed the space. Highly recommend an SUV/Jeep and be mindful they drive on the left! Condo is located at the top of the resort where the parking lot is located a short walk up a hill, not near the condo. We drove down to condo to unload in the small circle and managed to turn around without incident. The condo is located down 3 short flights of stairs. The condo buildings and grounds look tired, railings are loose. Once inside condo, you will be mesmerized by how nice and comfortable it feels - bed and pillows are very comfortable. Kitchen has everything you'll need - we shopped at both The Market at Tutu Mall and Moes in Red Hook for food - Moes is much nicer, everywhere is expensive! We drove down to the pool closest to the ocean, very clean. We did not go to restaurant. Coki Beach is within a walk but we found it extremely crowded and trash everywhere.

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.

House by the Sea “with back-up power”
We absolutely loved our stay! Beautiful views with clean and comfortable spaces. Rinsing off & enjoying the pool after a long beach day was so relaxing. The outdoor shower is incredible as well! Highly recommend taking their suggestion and renting a 4x4 to explore & easily get up the driveway. Overall, we had everything we needed and would definitely visit again!
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

"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!

REGATTA R&R
Excellent location ! Would definitely stay here again! Love bolongo bay area in general but Kendra's place is amazing!

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!!

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
Quick stats about holiday rentals with a pool in Anna's Retreat
Total rentals
70 properties
Nightly prices starting at
$201 AUD 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