
Holiday rentals with a pool in Charlotte Amalie
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Charlotte Amalie
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

BEST REVIEWS on the East End - HANDS DOWN!
ALWAYS BOOK with an ON-SITE LOCAL to get the INSIDE SCOOP. Book this condo to gain access to custom-made handouts to help you plan a memorable vacation! You'll love the KILLER VIEW of the Caribbean Sea about 200 feet away. This condo includes toys and games, and plenty of beach toys, noodles, and extra chairs for beach hopping! I'm frequently booked, so check out my other condos in Cowpet Bay West. airbnb.com/h/stthomasparadise10 airbnb.com/h/stthomasparadise26 airbnb.com/h/stthomasparadise42

Hillside Hideaway
Perfect getaway for an island getaway, business, or solo adventuring. This well appointed one bedroom apartment is nestled in a quiet central hillside neighborhood with views of Hans Lollik, Jost Van Dyke, and Tortola islands. Conveniently located one mile from Magen's Bay and ten minutes to downtown Charlotte Amalie by car. Rental car is a must! Come enjoy the tranquil views, take a dip in the pool, and experience St. Thomas like a local. Please read all listing details and house rules.

Honeymoon-Worthy w/ Pvt Pool Walk 2 Sapphire Beach
We fell in love with the island of perpetual summer. There's something special about having your own villa w/ a private pool. We also love the garden shower & the location. Pangea, the restaurant on site is phenomenal. The property is so close to our fave spots. Beautiful Sapphire Beach is in walking distance via a gate at the south end of the property. It boasts the Beach Buzz coffee & bfast spot, a Beach bar & grill w/ live music weekly, Paradise Pie pizza & SeaSalt fine dining restaurants.

Sunrise Cottage - Secluded, Romantic, Private
Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Ocean View Condo near Magen’s Bay - Pool/Generator
Welcome to your retreat with panoramic ocean views located in Mahogany Run, 5 mins from Magen's Bay Beach. Enjoy spectacular views of the ocean from every room of the condo. This bright and airy condo is equipped with a plush king-size bed, a fully equipped kitchen, and a bathroom featuring a walk-in shower. Spend the days at one of the island's beaches, snorkeling, hanging out by the pool, or exploring downtown Charlotte Amalie! We HIGHLY recommend renting a car to get around the island

Private Pool in Paradise! Ocean View Steps 2 Beach
Come enjoy the island life at this tranquil villa with private pool...only steps from the beach! Cooler, snorkeling gear, and beach chairs INCLUDED! The entire home has been remodeled. The pool has been fully updated as well as the deck area, which includes brand new furniture and high-end loungers. A new gas grill has also been added for your outdoor grilling pleasure. Stream all your favorites with our strong Wi-Fi. Upscale restaurant, Pangea, is just steps away. Free parking.

Rockroom One Bedroom Condo at The Hills Saint John
"The Rockroom" is a one bedroom apartment located within The Hills Saint John. This large space with amazing views of Cruz Bay and St Thomas features a large bedroom with King bed, two full baths, a large living area and a full kitchen. There is also a large private patio with a gas grill and patio furniture. Guests staying at Rockroom will also have access to The Clubhouse Bar (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

Oceanfront Bliss & Perfect Sunsets + Backup Power
Our fully renovated 1BR/1BA condo is PERFECT for couples, small families or a friends getaway. Enjoy stunning ocean views and the sound of waves from every room or your private balcony. Watch breathtaking sunsets and cool off in one of three crystal-clear pools. Located in a gated community, just steps from the beach, oceanside pool, and seaside dining. Only 10 min to Red Hook (ferries to St. John & BVI) and Havensight, and 15 min from the airport—your perfect island escape! 🌴

Chic 1 Bedroom Oasis with Designer Decor & Pool
Welcome to our impeccably designed oversized 1-bedroom apartment (+ queen size Murphy bed) a stylish retreat that promises an unforgettable stay in the heart of the historic district of Charlotte Amalie with its own plunge pool and deck. This apartment boasts a sophisticated ambiance, curated with the finest designer furnishings, decor and lighting as well as a custom kitchen. This is a perfect location to serve as the base to explore St. Thomas and the surrounding islands.

Sunshine Daydream - Our little piece of paradise!
Spend your days between at Sunshine Daydream with its beautiful ocean views. Rise up to paradise enjoying the gorgeous sunrises and sunsets from the private rooftop deck. This rental offers a fully equipped kitchen, 3 different pools, one of which is steps from the condo. There is easy beach access and we are centrally located between Charlotte Amalie and Red Hook. To top it off there are 2 restaurants and a bar within walking distance from the unit.

View of Magen’s Bay Beach
The apartment is very close to a private beach below. The community is private which has now turn into a gated community. If you love jogging since the traffic is not high the area has jogging or walking. Transportation is needed. President Clinton stayed in this area villa just below. I am retired and I enjoy hosting also I am easy to get along with. There are beach chairs, snorkeling equipment and beach towels available for your use.

Esperance~Pool~New~National Park
Spacious 2BR, 2BA luxury apartment in Fish Bay Skytop with full kitchen and washer/dryer. Both bedrooms feature Loom & Leaf memory foam mattresses. King bedroom with en-suite bath, second bedroom with queen bed and bathroom across the hallway. Smart TV with Netflix and streaming apps (no cable). 10 min drive to Cruz Bay dining, shopping, groceries, 25 min to North Shore beaches. 4 ft shared pool and BBQ with two other apartments.
Popular amenities for Charlotte Amalie rentals with a pool
House rentals with a pool

Villa Bliss - 3 Bedroom Island Oasis

Island Retreat - Generator/Ocean View/Heated Pool

Quirky Charm~ Killer Pool and Jaw Dropping Views!

Stunning View, Magens Bay, Pool, Amazing Villa!

Caribbean Poolside Cottage

Private Pickleball Court - 5 min walk to Beach

3 BR Villa with Stunning Harbor Views

Ylang Ylang - Luxury 2 Suite Villa in Cruz Bay...
Apartment rentals with a pool

SunnySide Villa! 2BR/3BA in Margaritaville resort

Sapphire Blue Sea View

Book Now! Caribbean Sunshine! Amazing Views!

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

REGATTA R&R

Romantic Private Pool Villa@Sapphire. Generator.

Luxury 1/1 Oceanfront @ Sapphire Beach Resort

Wrap Around Balcony~Views~Pack your Bathing Suit!
Other holiday rentals with a pool

Villa Crystalia Oceanside condo

Good Vibes Only Ocean Villa-Views/Pool/Sundeck/Fun

Layah's Vista

Condo with Northside Views & Back-Up Generator

Generator! Top Floor Condo - 5 mins to Magens

Seaview in St. Thomas

Amazing Ocean View 2BR/2BA Condo Near Magens Bay

Steve’s Seaside Condo | 2BR | 3 Pools | Southside
When is the best time to visit Charlotte Amalie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £277 | £288 | £282 | £285 | £288 | £230 | £241 | £206 | £221 | £221 | £288 | £266 |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°C |
Quick stats about holiday rentals with a pool in Charlotte Amalie

Total holiday rentals
Explore 50 holiday rentals in Charlotte Amalie

Nightly prices starting at
Charlotte Amalie holiday rentals start at £67 per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Charlotte Amalie holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Charlotte Amalie rentals

4.7 Average rating
Charlotte Amalie stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Punta Cana Holiday rentals
- San Juan Holiday rentals
- Bayahibe Holiday rentals
- La Romana Holiday rentals
- Carolina Holiday rentals
- Juan Dolio Holiday rentals
- Culebra Holiday rentals
- Sainte-Anne Holiday rentals
- Saint Thomas Holiday rentals
- Little Saint James Holiday rentals
- Saint Croix Holiday rentals
- Aguadilla Holiday rentals
- Rentals with beach access Charlotte Amalie
- Rentals with a hot tub Charlotte Amalie
- Flat rentals Charlotte Amalie
- Pet-friendly rentals Charlotte Amalie
- Rentals with outdoor seating Charlotte Amalie
- Rentals with a washing machine and dryer Charlotte Amalie
- Fitness-friendly rentals Charlotte Amalie
- Rentals with a patio Charlotte Amalie
- Villa rentals Charlotte Amalie
- House rentals Charlotte Amalie
- Family-friendly rentals Charlotte Amalie
- Rentals with pools Saint Thomas
- Rentals with pools U.S. Virgin Islands
- Flamenco Beach
- Limetree Beach
- Honeymoon Beach
- Magens Bay Beach
- Coki Beach
- Secret Harbor Beach
- Cane Garden Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Virgin Islands National Park
- Peter Bay Beach
- Josiah's Bay
- Sugar Beach
- Maho Bay Beach
- Coral World Ocean Park
- Sun Bay Beach
- The Baths
- Cane Bay
- Isla Palomino
- Lindquist Beach
- Brewers Bay Beach
- Cond Marina Lanais
- Paradise Point Tranway
- Point Udall




