
Holiday rentals with a pool in Cruz Bay
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Cruz Bay

Total holiday rentals
Explore 520 holiday rentals in Cruz Bay

Nightly prices starting at
Cruz Bay holiday rentals start at $128 SGD per night before taxes and fees

Verified guest reviews
Over 6,560 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wifi availability
510 of Cruz Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cruz Bay rentals

4.9 Average rating
Cruz Bay stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with a pool in Cruz Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Upper Grande Bay-Studio King plus 1 foldout
FRESH AND UPDATED studio unit in the heart if Cruz Bay at Grande Bay Resort. King bed studio suite with a full foldout sofa, Kitchenette & living room seating area, washer dryer. Amazing view from inside & balcony perched high up on the hill over looking Cruz Bay and surround. Great for a honeymoon, anniversary, or any getaway! Very clean unit & well appointed furnishings. . Wake up to the Caribbean Blue water & sun! Please note. PARKINGis NOT included-paid parking offsite or taxis
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2 Bed ⭐️ STAR VILLA HOME ⭐️ 5 Min walk to CRUZ BAY
Star Villa is a spacious 1-story retreat offering comfort, privacy, & effortless island living. ⭐️ With 2 air-conditioned bedrooms and 2 baths, the villa features domed ceilings, rattan furnishings, and cool tile floors throughout. Large windows & sliding doors welcome island breezes & beautiful views. A wraparound deck opens to a private freeform pool, while the living area flows into a full kitchen and formal dining space, ideal for families or couples seeking a relaxed, upscale stay. 💕
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Sweet Spice: A Nifty Little Cottage. With A Pool!
This very small 1 BR cottage lives BIG with a screened porch, SOLAR POWER, valley views, 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.
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Mar de Amores great Views, private pool generator
At this villa we offer the best cleaning and sanitization practices . Long term rentals are also welcome. This is a three bedrooms villa which offers the most magnificent 180 degree views of four bays: Rendezvous , Hart , Chocolate Hole and Great Cruz Bay, St Croix and Pillsbury Sound to the west, in St John. All bedrooms are under the same roof; the balcony and the pool are facing the sea. 3 bedrooms - 2 bathrooms, amazing garden and ample space for parking. Ample wifi and very private pool.
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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.
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Sail Away II-WOW Beachfront to Paradise Remodeled
Full property generator. Sail Away II at Sapphire Beach Resort and Marina is located on the beachfront just steps away from the sparkling Sapphire Beach. The patio leads you to a dazzling infinity pool and the option of 2 immaculate beaches. Caribbean water and amenities galore await you. No need to leave the tranquility of your room thanks to the many home furnishings within your vacation paradise. Beach level, beachfront & lush surroundings is yours to escape the hub of city life.
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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.
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Wild Ginger at Casa Tre Fiori
Wild Ginger at Casa Tre Fiori is located in beautiful, peaceful Fish Bay on St John. Sit and relax over the garden on the large covered deck while listening to the birds and watching the deer. The property enjoys an acre filled with fruit trees and gardens. Enjoy the shared pool and hot tub after a fantastic day of snorkeling and exploring St John’s world famous beaches. Wild Ginger is on the the main level of Casa Tre Fiori. Located approximately 4 miles from Cruz Bay.
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Seascape Villa with private pool in Cruz bay
Seascape Villa is spacious magnificent four bedroom suites on one floor. It’s located on a private cul-de-sac of Estate Pastory near Caneel Hill Trail with spectacular views of Caribbean water, mountains and surrounding cays. The location is close to the town of Cruz bay but yet peaceful and private. The property is gated for an extra layer of privacy and lush landscaped with a private pool and an outdoor kitchen. AN ENTIRE HOUSE BACK UP GENERATOR FOR POWER OUTAGE.
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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.
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Hilltop Paradise Vacation Package with Jeep
Start your next adventure and step into this brand new contemporary modern home hidden in the hills of St. Thomas. Here, you will be greeted with incredible, breathtaking views and an infinity pool overlooking the beautiful Charlotte Amalie. This carefully designed retreat sets the tone for a perfect adventure getaway for a group of friends/couples, or the perfect relaxation stop for a family. Whatever you choose, this home will not disappoint.
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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.
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Popular amenities for Cruz Bay rentals with a pool
House rentals with a pool

Private Pool in Paradise! Ocean View Steps 2 Beach
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Stone Cottage with a pool and gorgeous view
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Villa Beso Del Sol - Three Bedroom Cozy Oasis
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Entire villa with beautiful views! Amazing
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Panoramic Ocean views and off Grid
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Pool - Ocean View - Large Deck & Pergola - Private
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3BR/3 BA LUX Pool Villa*Cruz Bay*Auto Generator
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Caribbean Cottage Near the Sea
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Apartment rentals with a pool

Wrap Around Balcony w/Amazing Views! Remodeled!
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Sunrise Sapphire West-A Building-NEW AC-
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Ocean Front Steps to beach w/ pool and restaurant
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Wrap Around Balcony~Views~Pack your Bathing Suit!
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Killer View; Book w/a Local for the Inside Scoop!
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Island View Retreat | Stunning Ocean Views!
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Oceanfront Bliss & Perfect Sunsets + Backup Power
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Seas The Day
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Other holiday rentals with a pool

Gorgeous ocean view penthouse! Walk to Cruz Bay!
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Villa Hermosa - Beautiful with Pool & Ocean Views
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Latitude Adjustment at Grande Bay Resort, St John
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Ginger Thomas Villa in Cruz Bay
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Elysium Villa | Secluded Ocean Views, Private Pool
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Oceanfront - Perfect couple only romantic getaway
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Just Peachy - Pool Villa + Bronco + WE’RE SOLAR!
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Mandavilla| Pool/Cruz Bay Views/Starlink&Generator
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When is the best time to visit Cruz Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $996 SGD | $1,079 SGD | $1,079 SGD | $952 SGD | $886 SGD | $863 SGD | $789 SGD | $802 SGD | $742 SGD | $726 SGD | $775 SGD | $970 SGD |
| 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 |
Destinations to explore
- Flat rentals Cruz Bay
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- Villa rentals Cruz Bay
- Pet-friendly rentals Cruz Bay
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- Hotel rooms Cruz Bay
- Rentals with beach access Cruz Bay
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- Resort rentals Cruz Bay
- Luxury rentals Cruz Bay
- Beachfront rentals Cruz Bay
- House rentals Cruz Bay
- Family-friendly rentals Cruz Bay
- Rentals with a kayak Cruz Bay
- Rentals with pools St. John
- Rentals with pools U.S. Virgin Islands
- Flamenco Beach
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Secret Harbor Beach
- Honeymoon Beach
- Cinnamon Bay Beach
- Virgin Islands National Park
- Cane Bay Beach
- Limetree Beach
- The Baths
- Peter Bay Beach
- Maho Bay Beach
- Coral World Ocean Park
- Josiah's Bay
- Cane Bay
- Paradise Point Tranway
- Brewers Bay Beach
- Lindquist Beach
- Cruz Bay
- Sandy Point Beach
- Point Udall
- Culebrita Beach
- Coki Point Beach





