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

The Tile House
Enjoy breathtaking sunsets views over the turquoise Caribbean waters and the surrounding cays from our newly renovated two bedroom villa with indoor plunge pool. Our ocean view villa is richly appointed with modern furnishings and appliances, designed with comfort and convenience in mind. Watch the ferries, sailboats and cruise ships sail by as you enjoy the breathtaking island sunsets over Cruz Bay, St. John. The Tile House is solar powered with Tesla battery backup and reliable high speed internet to ensure your island experience is uninterrupted. Take a refreshing dip in the indoor plunge pool after a hot day at the beach. Book your St. John vacation today! What Makes Our Villa Unique? You are within a 5 minute drive (10min walk) of supermarket, pharmacy, gas station, post office, dining, and entertainment. Patio overlooking Cruz Bay, Pillsbury Sound and sunsets over St. Thomas One King and One Queen Bed Indoor plunge pool Private Parking Driveway Private Entrance Dedicated work desk and high speed internet Fully equip kitchen with side by side fridge, commercial stove, appliances including coffee maker and toaster, cookware, table settings, towels, and soap Washer/ Dryer (supplies included) Great room with smart TV set up for your use Curated high-end and hand-crafted décor and furnishing Mini Fridge - available for stock of local beverages (found only on the island) upon request Beach towels and gear provided Notes Rent a 4x4 vehicle to get up and down our island hillside road. It is possible to make the walk though we highly encourage renting a 4x4 vehicle for your stay. No sedans. $250 Cleaning and Prep fee per stay Owners reside on lower premise of property. Your privacy and enjoyment of our rental villa is our highest priority. If any issues arise during your stay, property management will be available to address expeditiously.

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. 💕

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

Peaceful Island Getaway w/ Pool & Tropical Charm
Sol-Azul Tropical Island Escape~ This peaceful and stylish retreat is full of Caribbean charm and made for relaxation. *A sparkling pool surrounded by lush tropical landscaping *Spacious covered porch for morning coffee or entertaining *Bright, airy interiors w/ island-inspired decor *Just minutes from town, restaurants, and gorgeous beaches Whether you're here to unwind by the pool, explore island flavors, or soak up the sun on sandy shores, this home is the perfect base for your vacation!

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.

Esperance~Pool~New~National Park
Spacious freshly built 2 Bedroom, 2 bathroom luxury apartment with fully equipped Kitchen and washer/dryer. Both Rooms have a memory foam mattress from Loom and Leaf. One king bedroom with en-suite bathroom, the second bedroom has a queen bed with a bathroom right across the room. Conveniently located 10min drive from Cruzbay's world class dining, shopping, grocery markets, and entrance to the North Shore Beaches. 4ft deep, shared new Pool with 2 other Apartments. shared BBQ by the Pool.

OceanView! 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

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.

Latitude Adjustment at Grande Bay Resort, St John
A waterfront, spacious luxury 1 BR/1 BA condo, sleeps 4, with full kitchen. Sip rum punches and watch island sunsets from the high granite bar on the full-length deck, all overlooking the azure waters of Cruz Bay and the marina. New listing in excellent condition with modern artwork and high-quality furniture, A/C, ceiling fans and tile floors. Spacious living/dining area with expansive waterfront views. Includes: beach chairs, cooler, etc. and 1 reserved covered parking space.

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.

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.

Caribbean Cottage Near the Sea
Paradise! The cottage is located on Hart Bay, and has an amazing view of the Carribean Sea. You can fall asleep to the sound of waves. You will stay in the upstairs one bedroom apartment with your own private entrance. The owner’s live in the lower level. Private pooI area. It’s an older cottage with an outdoor shower. There are 67 uneven steps down to cottage from parking area. There are steps that lead to a trail and rocky beach. Property has a generator.
Popular amenities for Cruz Bay rentals with a pool
House rentals with a pool

Down Yonder Pool Villa / Full Solar & Battery

La Sirena Secluded Villa w/Pool+NEW Solar backup!

Villa De Vida

St John Brand new 2 bedroom stunner

Spectacular Views - 3-5 bedrooms Cruz Bay, St John

VIewtiful: Virgin Islands Views

Texas Embassy

Palladio's View - Private Villa With Pool & AC!
Apartment rentals with a pool

Charming Beach Condo w/ Balcony- 2 Pools and Beach

BEST REVIEWS on the East End - HANDS DOWN!

Sunrise Sapphire West-A Building-NEW AC-

Cold? Book Now! Caribbean Sunshine! Amazing Views!

"H2Oh What a Beach!" condo: Walk-out Beach Access!

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

Sail Away II-WOW Beachfront to Paradise Remodeled

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

El Nido, a beautiful place to stay in paradise!

BEAUTIFUL GRANDE BAY STUDIO CONDO W/ GREAT VIEWS

Poolside Paradise at Castaway (newly renovated)

Milk Moon Cottage

1 mile to town, comfortable, steps from the pool.

Mango Breeze the perfect condo! NEW POOL!

Just Peachy - Pool Villa + Bronco + WE’RE SOLAR!

Private Pool 1 bedroom Ocean view
When is the best time to visit Cruz Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $1,007 SGD | $982 SGD | $973 SGD | $887 SGD | $746 SGD | $734 SGD | $785 SGD | $798 SGD | $738 SGD | $723 SGD | $771 SGD | $965 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 |
Quick stats about holiday rentals with a pool in Cruz Bay

Total holiday rentals
Explore 490 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 5,490 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
180 properties have a dedicated workspace

Wifi availability
480 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!
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- Flamenco Beach
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- Peter Bay Beach
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