Vacation rentals with a pool in St. John

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Top-rated rentals with a pool in St. John

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

Cottage in Coral Bay

5.0 out of 5 average rating, 79 reviews

Sweet Spice: A Nifty Little Cottage. With A Pool!

This very small 1 BR cottage lives BIG with a screened porch, solar, valley views, bedroom ac, dishwasher, outdoor fitness, and plunge pool. With a clean modern vibe, Sweet Spice is more laidback getaway than luxury villa. It’s an ideal HQ for 2 active STJ adventurers - but with a few extra amenities! Located off the beaten path on the quiet side of STJ, it feels secluded but is only a 5 minute drive to the shops of Coral Bay. Note: road is rough and requires a 4WD and there are LOTS of stairs.

Oct. 3 – 10

$448 CAD per night

Guest favourite

Villa in Coral Bay

4.93 out of 5 average rating, 85 reviews

Heaven's Gate - Spectacular Panoramic Ocean View

This Mediterranean style, four bedroom luxury villa sits at the top of a mountainside overlooking St. John’s pristine Hurricane Hole, designated a Virgin Islands Coral Reef Monument in 2001. Heaven’s Gate is a serene and very private hilltop vacation villa. Each of the four handsomely furnished bedroom suites includes its own private bath, three with outside showers, and each suite has access to outside terraces. Please review the House Rules prior to booking. Compliance is mandatory.

Oct. 10 – 17

$1,134 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

Home in Coral Bay

4.99 out of 5 average rating, 102 reviews

Paradisea 2 Bedroom with pool

2 cozy bedrooms, fully equipped kitchen, large decks and pool. Everything you need for a day at the beach: chairs, umbrella, coolers, floats, toys, towels all provided. Paddle boards available for rental $100 a week. Close to Coral Bay restaurants and shops. North Shore beaches and hiking trails are only a short drive away. Quiet setting in the hills above Coral Bay. Close to it all with a far away feel. good for couples, solo adventurers, and families with children over the age of 10.

Aug. 31 – Sep. 7

$543 CAD per night

Guest favourite

Villa in St. John

4.97 out of 5 average rating, 30 reviews

Just Peachy - Pool Villa + Bronco & 1/2 day Dinghy

Nestled on the mountainside of Gifft Hill, this charming St. John home will give your group peace and comfort away from the crowds. Relax on the wrap-around porch, watch the sunset over Pilsbury Sound, listen to the Coqui frogs, and lounge on the newly updated pool deck. The nightlife of Cruz Bay is less than ten minutes away, and the National Park Beaches are about fifteen minutes. Close enough to all of the tourist action, but you won't have to sacrifice peace and comfort for proximity.

Oct. 5 – 12

$1,061 CAD per night

Guest favourite

Villa in Coral Bay

5.0 out of 5 average rating, 46 reviews

Memory Daze

Welcome back to Memory Daze! The perfect setting for couples retreat or small group. Plenty of open shared outside space as well as private bedroom nooks for when you want some quiet time. Children allowed 12 years and older. This beautifully appointed Caribbean Style villa, boasts amazing down island views, large pool, lush gardens, gated parking and native stone and artistic tile work. The estate is perched along a ridge facing southeast down island, with very easy access to Coral Bay.

Nov. 29 – Dec. 6

$942 CAD per night

Guest favourite

Villa in Central

5.0 out of 5 average rating, 25 reviews

Mykonos- freshly built Greek Inspired Luxury Villa

Mykonos Villa- A Greek inspired Luxury Villa. This private property is located in one of the most sought after areas offering un interrupted breath taking views of St. John’s south shore. Conveniently located a short drive from Cruz Bays world class dining, shopping, and the entrance to the North Shore beaches. Our 2 level villa , 3 suite king bedrooms, fully equipped kitchen, living room, balconies, with elegant and modern decor gives a comfy luxury experience plus your own private pool

Oct. 7 – 14

$1,745 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

Villa in Central

5.0 out of 5 average rating, 6 reviews

Brizan. A Quiet Reef Bay Villa

BRIZAN is a private 3BR/3BA villa nestled just above Reef Bay, offering Caribbean views, tropical breezes, sunrises, sunsets and night skies from every room. The single-level design, with deck, pool and spa, create 6,000 sq. ft. of private indoor/outdoor space. BRIZAN borders the undeveloped US Virgin Islands National Park, and is a quick (~10 min) hike to the white sand beach below. Sleeps 6 guests comfortably. Includes island concierge and pre-arrival provisioning!

Sep. 12 – 19

$872 CAD per night

Guest favourite

Cottage in Hansen Bay

5.0 out of 5 average rating, 58 reviews

Milk Moon Cottage

Situated on the quiet and serene East End of St. John, Milk Moon Cottage is a private oasis overlooking the British Virgin Islands. The cottage features striking views, convenience to East End beaches, and plenty of amenities to make guests feel right at home. *** KEY FEATURES *** -Two bedroom, two bathroom home with air-conditioning throughout -Full-sized kitchen -Completely private pool -WiFi -Beach chairs, beach cooler with ice packs, & beach towels all provided

Apr. 7 – 14

$1,053 CAD per night

Guest favourite

Home in St. John

5.0 out of 5 average rating, 28 reviews

Villa Hermosa - BEAUTIFUL with Pool & Ocean Views

Villa Hermosa is a luxury masonry constructed home located on the hillside overlooking Fish Bay on St. John, USVI. The villa has 3 bedrooms and 3.5 bathrooms. Villa Hermosa provides spacious living areas with beautiful finishes, stonework and craftsmanship. Villa Hermosa is fully equipped for your family and friend vacation on St. John. The villa provides all your basic amenities and supplies to ensure you are prepared for an enjoyable and comfortable stay.

Aug. 19 – 26

$1,134 CAD per night