Holiday Homes in Charlotte Amalie

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Charlotte Amalie

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
Relax by the pool with a view of the sea and distant mountains.

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!

9.6 out of 10, Exceptional, (21)
"Very much enjoyed the stay. Spectacular view!!!"
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
Sapphire Breeze, Majestic Views & Island Vibes w/ Infinity Pool, Waterfall & Covered Porches
Enjoy breathtaking ocean views from the comfort of your room, featuring a large bed and a balcony with additional seating.

Sapphire Breeze, Majestic Views & Island Vibes w/ Infinity Pool, Waterfall & Covered Porches

9.6 out of 10, Exceptional, (15)
"This property exceeded our expectations in every way! We had a fantastic stay on St. John with three families - the house was perfect for kids and adults alike. The view from the infinity pool will blow your mind. We can’t wait to come back! "
Sapphire Breeze, Majestic Views & Island Vibes w/ Infinity Pool, Waterfall & Covered Porches
"Someday Soon" Has Arrived!
Relax by the tranquil pool overlooking a lush island and calm sea, surrounded by sailboats.

"Someday Soon" Has Arrived!

9.8 out of 10, Exceptional, (68)
"Wonderful stay that provided everything we needed for a great first time in St. John. Home was clean, and bed was very comfortable. A quaint place that we would come back to. Pool and view make this a special place."
"Someday Soon" Has Arrived!
Alta Vista - Mint condition property- 50 mile views!
Relax by the serene pool, surrounded by a gentle waterfall and breathtaking views of the rolling hills and coastline.

Alta Vista - Mint condition property- 50 mile views!

10.0 out of 10, Exceptional, (59)
"All I heard all week from family was “wow! This place is nice”. The views, the comforts, the amenities (pool, hot tub) were essentially all we needed. If the island wasn’t so beautiful we may have never left. The property managers were very helpful meeting us and leading us to the house. The location is fabulous for visiting all the beaches. And, Coral Bay is close for fresh seafood and basic groceries. "
Alta Vista - Mint condition property- 50 mile views!
The Cottage at Villa Indigo
Cozy living space with a sofa, ottoman, and dining area, featuring a kitchenette and natural light.

The Cottage at Villa Indigo

3.0 star property
8.8 out of 10, Excellent, (15)
"We love St. Thomas This property was in a safe location as long as you are willing to drive on the left side of the road."
The price is NZ$763
includes taxes & fees
11 Aug - 12 Aug
The Cottage at Villa Indigo
Stunning In-town Estate Cruz Bay Villa! Walk to Downtown. Private Pool. Views. Back up Power. All Bedrooms en Suites with King Beds.
Relax by the infinity pool with a view of the surrounding landscape, or unwind in the adjacent outdoor seating area.

Stunning In-town Estate Cruz Bay Villa! Walk to Downtown. Private Pool. Views. Back up Power. All Bedrooms en Suites with King Beds.

9.8 out of 10, Exceptional, (75)
"Our group of 9 had a wonderful stay at the property. The house was spacious for all of us and the location was perfect to walk to restaurants and shops. "
Stunning In-town Estate Cruz Bay Villa! Walk to Downtown. Private Pool. Views. Back up Power. All Bedrooms en Suites with King Beds.
Mampoo Hill-- a Beachfront House 20 Yards from the Ocean with optional Jeep
Guests can enjoy a scenic ocean view from this seaside terrace, featuring a seating area with chairs and a table.

Mampoo Hill-- a Beachfront House 20 Yards from the Ocean with optional Jeep

10.0 out of 10, Exceptional, (103)
"Terrific location, terrific host, loved every minute of our stay."
Mampoo Hill-- a Beachfront House 20 Yards from the Ocean with optional Jeep
Amazing Caribbean Getaway W/ Spectacular Views Sleeps 12
Escape to a serene beach setting with turquoise waters and a secluded rocky shoreline.

Amazing Caribbean Getaway W/ Spectacular Views Sleeps 12

9.4 out of 10, Exceptional, (107)
"The living area was large and inviting, the kitchen was stocked with all the pots, pans, and everything to prepare our meals. Each bedroom had it's own bathroom. The living room was spacious comfortable. Secluded in a beautiful setting."
Amazing Caribbean Getaway W/ Spectacular Views Sleeps 12
Million Dollar Panoramic Views! Huge Decks and Pool!
Relax by the serene pool, surrounded by a tranquil landscape and a shaded gazebo.

Million Dollar Panoramic Views! Huge Decks and Pool!

10.0 out of 10, Exceptional, (143)
"We loved the setup - pool was excellent and the wraparound deck was great to get the sun/shade/breeze you wanted. Kitchen and grill were great as well. We would love to return in the future!"
Million Dollar Panoramic Views! Huge Decks and Pool!
Sunset Hideaway Suite - Oceanview/central to Cruz Bay
Enjoy the breathtaking view of the coastal town and sea from this outdoor terrace.

Sunset Hideaway Suite - Oceanview/central to Cruz Bay

10.0 out of 10, Exceptional, (2)
Sunset Hideaway Suite - Oceanview/central to Cruz Bay
Cara Mia beautiful 3 king BR, 3.5 bath, whole house generator views private pool
Relax by the serene pool surrounded by lush vegetation and enjoy comfortable seating in our spacious outdoor lounge.

Cara Mia beautiful 3 king BR, 3.5 bath, whole house generator views private pool

10.0 out of 10, Exceptional, (74)
"We enjoyed Cara Mia tremendously. The views were outstanding and continued to amaze us each day. The full rainbow we saw over the bay and hills was the best. Highly recommend staying at Cara Mia! "
Cara Mia beautiful 3 king BR, 3.5 bath, whole house generator views private pool
Amazing views and great location - 4 Bedroom Estate Bakekroe in St Thomas
Sun-loungers, beach towels

Amazing views and great location - 4 Bedroom Estate Bakekroe in St Thomas

9.0 out of 10, Wonderful, (14)
"Excellent property in a beautiful local. We loved the house, the pool and the surroundings!"
Amazing views and great location - 4 Bedroom Estate Bakekroe in St Thomas
2 Primary Bedrooms - POOL - Sleeps 10!
Relax on the spacious balcony overlooking the sea, featuring outdoor seating and a pool area.

2 Primary Bedrooms - POOL - Sleeps 10!

10.0 out of 10, Exceptional, (1)
"We had a great stay!! All the windows in the house offer great views.The interior was very high end with lots of space, extra blankets, pillows and towels.We had a minor issue with the water pump but they immediately came out and fixed it. We highly recommend this house! "
2 Primary Bedrooms - POOL - Sleeps 10!
3 Bedroom House w/ Car Overlooking Rendezvous Bay with AC in bedrooms.
Enjoy breathtaking views of the sea and distant land from this balcony.

3 Bedroom House w/ Car Overlooking Rendezvous Bay with AC in bedrooms.

9.8 out of 10, Exceptional, (45)
"Wonderful property with awesome views. Very spacious and clean. The bedroom air conditioners were great. We were there during a very warm and humid week so the main areas were warm but the open doors and breezes were very helpful. Use of the large car was such a bonus! We enjoyed our vacation "home-away-from home"!"
3 Bedroom House w/ Car Overlooking Rendezvous Bay with AC in bedrooms.
The Purple Flamingo at Flamingo Gardens
Relax by the serene pool surrounded by lounge chairs and tables, with a panoramic view of the surrounding landscape.

The Purple Flamingo at Flamingo Gardens

10.0 out of 10, Exceptional, (1)
The Purple Flamingo at Flamingo Gardens
Northside Villa, Pool + Views, Near Magens Bay
Pool

Northside Villa, Pool + Views, Near Magens Bay

Northside Villa, Pool + Views, Near Magens Bay
Luxury Ocean Front Estate / Breathtaking Views/Private Beach and Lagoon
Enjoy ocean views from the comfort of your room, where you can relax in a stylish space with a sofa, a table, and a decorative piece.

Luxury Ocean Front Estate / Breathtaking Views/Private Beach and Lagoon

10.0 out of 10, Exceptional, (89)
"Such a blessing to be able stay at this villa! Perfect for families, kids of all ages! Pool so much fun! Views are crazy and proximity 5 minute walk to one of the most beautiful beaches in the world! Thank you! Thank you! Highly recommend this property and location. See ya next year! "
Luxury Ocean Front Estate / Breathtaking Views/Private Beach and Lagoon
Sunset, Sunrise & Ocean Views, 3 Bed 4.5 Bath, Close to Cruz Bay & Beaches. Gym
Stroll along the brick pathway to a scenic overlook with breathtaking ocean views.

Sunset, Sunrise & Ocean Views, 3 Bed 4.5 Bath, Close to Cruz Bay & Beaches. Gym

9.8 out of 10, Exceptional, (36)
"As it was our first visit to St John, we weren’t completely sure what to expect; this house far exceeded our expectations! My husband and son loved the gym (it was better than advertised) and my daughter and I loved the pool and pool deck. The outdoor kitchen is wonderful and the views from the pool deck are breathtaking!! Would definitely reserve this house again without hesitation "
Sunset, Sunrise & Ocean Views, 3 Bed 4.5 Bath, Close to Cruz Bay & Beaches. Gym
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Relax by the pool surrounded by lush greenery and a serene hilly landscape.

Minutes from Magens Bay, gated property, large pool & outdoor entertainment area

10.0 out of 10, Exceptional, (32)
"Beautiful, well-appointed house was perfect for our group. Amazing view, fantastic pool and centrally located."
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
New home, Privately nestled w/ your own pool and spectacular views! Backup Power
Relax by the pool surrounded by a serene landscape with a clear view of the surrounding hills and water.

New home, Privately nestled w/ your own pool and spectacular views! Backup Power

10.0 out of 10, Exceptional, (88)
"The stone pathway steps up to the main level to the pool and view of the Coral Bay were beautiful. Great getaway for us and just a short trip down the mountain to laid back restaurants for good food and fun drinks! "
New home, Privately nestled w/ your own pool and spectacular views! Backup Power
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlotte Amalie Hotel Reviews

Pirates Pension at Bluebeard's Castle

Pirates Pension at Bluebeard's Castle

10/10 Excellent
"Good stay!"
Tesca 1-night trip
Posted 9 hours ago
Pirates Pension at Bluebeard's Castle