Vacation rentals with a pool in Cruz Bay

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Top-rated rentals with a pool in Cruz Bay

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Chocolate Hole

5.0 out of 5 average rating, 38 reviews

Down Yonder Private Pool Villa

Beautiful island memories are made at Down Yonder Pool Villa. Surrounded by lush tropical gardens and conveniently located in Chocolate Hole (less than .5 miles from the Westin resort), this well-appointed, comfortable home features two King suites - one on either side of the huge Great Room. The Great Room and each bedroom enjoys access to the glorious sundeck and 30 foot salt water pool, and every room has the same mesmerizing view of Chocolate Hole Bay and the deep blue Caribbean water beyond. Rates based on four persons occupancy. Additional guest fees apply for more guests up to 6 total. Click "Book Now" for detailed quote.

Mar. 16 – 23

$1,054 CAD per night

Guest favourite

Condo in Cruz Bay

4.97 out of 5 average rating, 34 reviews

New! Island Therapy Studio - amazing views-St John

Island Therapy Contemporary Studio -sleeps 4 (queen bed + queen sleeper sofa) in St. John. New listing-excellent condition with modern furniture, AC, and tile floors. Expansive views of Cruz Bay, flat screen cable TV, internet, fully equipped kitchenette (coffee maker, microwave, small fridge, toaster, blender, single electric burner), washer/dryer. Enjoy island sunsets from the balcony deck with granite bar and chairs overlooking the islands. We fell in love with St John and know you will too.

Dec. 4 – 11

$712 CAD per night

Superhost

Condo in St Thomas

4.8 out of 5 average rating, 326 reviews

"Sunrise Sapphire" Sapphire Village

This is our newly renovated studio at Sapphire Village overlooking Sapphire Beach post Hurricanes Irma and Maria. We offer High Speed WiFi with Smart TV. Resort style bathroom with beautiful custom tile shower. New Kitchen with Granite counter tops and custom reclaimed timber shelves from Kansas City. Kitchen equipped with glass range, microwave, coffee pot, full size refrigerator and all the cooking utensils you’ll need. King size bed overlooking the beach! 2 pools and 1 restaurant on site!

Jul. 11 – 18

$210 CAD per night

Guest favourite

Apartment in Saint Thomas

4.97 out of 5 average rating, 153 reviews

Hillside Hideaway

Perfect getaway for island romance, 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.

Sep. 8 – 15

$220 CAD per night

Guest favourite

Tiny homes in St. John

4.92 out of 5 average rating, 159 reviews

Bogie's Villa, Tektite, Island Tiny Living

Large views directly across Pillsbury Sound over Thatch Cay to St. Thomas from your very own tiny living space. Situated on the pool deck this small space is ideal for a couple or single looking to get away from it all (including heavy packing), and get out exploring. Tektite provides everything you need for meals at home, a shared pool, laundry on site, and solar with battery backup. Beach towels, a small cooler and camp chairs are supplied for your beach days. *Updated with A/C and T/V*

Aug. 12 – 19

$294 CAD per night

Guest favourite

Apartment in Fish Bay

4.94 out of 5 average rating, 154 reviews

Jasmine at Casa Tre Fiori

Jasmine at Casa Tre Fiori is located in the peaceful neighborhood of Fish Bay on beautiful St John. An adorable cozy private one bedroom apartment with a kitchenette, which includes a refrigerator, microwave, two burner stove. Wifi. Dish TV. AC in Bedroom with King bed. Living area AC. Private patio. Shared pool. This is a no smoking property. Adjacent rentals can be added for larger groups. See Orchid at Casa Tre Fiori, Wild Ginger at Casa Tre Fiori and Cactus Flower Cottage.

Apr. 8 – 15

$341 CAD per night

Guest favourite

Home in Cruz Bay

4.9 out of 5 average rating, 42 reviews

2 Bed ⭐️ STAR VILLA HOME ⭐️ 5 Min walk to CRUZ BAY

Star Villa is a one story vacation rental villa with two air-conditioned bedrooms and two bathrooms. This spacious villa with domed ceilings has rattan furniture and floor tile throughout. Large windows and sliding patio doors allow cool breezes and magnificent views for a real Caribbean feeling. An expansive deck wraps around two sides of Star Villa and leads you to your very private freeform swimming pool. The living room is adjacent to a full kitchen and formal dining room.

Oct. 18 – 25

$699 CAD per night

Guest favourite

Condo in Cruz Bay

4.95 out of 5 average rating, 64 reviews

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 Bistro (located on the property) as well as a 24 hour fitness center and community pool.

Aug. 27 – Sep. 3

$444 CAD per night

Guest favourite

Cottage in Cruz Bay

5.0 out of 5 average rating, 56 reviews

Sol~Azul Cozy Studio Cottage w/ Pool & Ocean View

Fully equipped, spacious studio with full kitchen. Beautiful view of the sea and St Thomas in a peaceful neighborhood near Cruz Bay. Easy to navigate roadways with flat driveway and plenty of parking. Enjoy a nice evening on the pool deck to watch the sunset. Conveniently located 10 min from beaches and shopping. Beach Chairs & Towels provided. Laundry on-site. Shared Grill and Pool area w/ the Main Villa on property. Perfect for a couples getaway.

Dec. 6 – 13

$465 CAD per night

Superhost

Condo in St. Thomas

4.84 out of 5 average rating, 147 reviews

Breathtaking Views from Sapphire Village

Enjoy our studio unit located in Sapphire Village Condominium development! Our unit is smoke-free, pet-free, fully air conditioned, and offers breathtaking views of neighboring USVI and BVI. We are offering a vacation home with the comforts that we would want while we are vacationing on the island. The unit features a king bed, new sliding doors to the balcony as well as a new split air conditioning unit. New internet router January 2024

Mar. 9 – 16

$221 CAD per night

Guest favourite

Apartment in Cruz Bay

5.0 out of 5 average rating, 101 reviews

Sieben Apartment * Pool* next to Hiking trails

Spacious Luxury 2 Bedroom, 2 bathroom apartment with fully equipped kitchen and washer/dryer. Both rooms have memory foam mattresses from Loom & Leaf. The master bedroom has 1 King bed with private bathroom, and the second bedroom can be set up as 2 Twin beds or 1 King bed. 10 min drive from Cruzbay, Restaurants and grocery Stores. Shared brand new Pool (4ft deep) with two other apartments. Shared BBQ by the Pool.

Apr. 4 – 11

$818 CAD per night

Guest favourite

Villa in Cruz Bay

5.0 out of 5 average rating, 7 reviews

Charming 2 Bed 2 Bath Villa with Infinity Pool

Welcome to Perelandra Villa, a 2-bedroom, 2-bath haven, featuring its own secluded infinity pool. Set amid vibrant greenery punctuated by vivid, aromatic blooms, this residence promises a serene ambiance for all guests. From the elevated deck to the invigorating pool, indulge in mesmerizing views of azure seas and Cruz Bay. Come dusk, capture the allure of the sunset, painting vivid Caribbean hues across the sky.

Mar. 15 – 22

$1,121 CAD per night