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Vacation 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.

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Guest favorite
The inviting pool area features lounge chairs on a wooden deck, with two bright blue float lounge mats resting in the water. Surrounding greenery complements the outdoor setting, while the backdrop showcases the elegant architecture of the villa under a soft evening sky.
Home in Cruz Bay
4.97 out of 5 average rating, 35 reviews

Villa De Vida

This stunning Chocolate Hole property combines luxury, privacy, nature, ocean views and outdoor living seamlessly. Floating in the pool listening to the ocean below it's easy to see why a budding young country star loved coming to Villa De Vida, his first home, to get some inspiration for some of his many number one hits. Each of the three bedroom suites is situated in its own private building, connected to the great room via covered walkways and picturesque arched entrance ways. Set up to to maximize privacy, each bedroom suite has their own deck and full bathroom, including an outdoor shower. A spacious kitchen and living room area opens to an expansive wood deck with a large mahogany table that is perfect for group dinners. In the mornings you can take a nature walk through the property while enjoying a cup of coffee and take in all of the natural beauty that you're surrounded in. You can spend all day enjoying the pool and relaxing on the daybeds, watching sunset and then taking in the twinkling lights of St. Thomas across the ocean. Video Tour Here

Guest favorite
A spacious pool deck features comfortable lounge chairs and a table, overlooking the Caribbean Sea and surrounding islands. The saltwater pool reflects the clear blue sky, providing a serene space for relaxation and enjoyment amidst the lush landscape.
Home in Cruz Bay
4.96 out of 5 average rating, 27 reviews

The yellow flamingo

Our Caribbean vacation property in St. John is the perfect destination for your next tropical getaway. There are stunning views of the Caribbean Sea, St. Thomas, Great St. James, and Little St. James make for a truly unforgettable experience. This is 1 of 3 units and sits below another unit. The lower house unit is a 1 bedroom and also has a sleeper sofa. You can unwind and soak up the sun on our pool deck that features a breathtaking saltwater pool and plenty of seating for family and friends.

Guest favorite
The outdoor terrace features lounge chairs positioned beside a private plunge pool, with expansive ocean views visible in the background. A comfortable seating area is situated adjacent to the pool, surrounded by lush greenery and a clear blue sky.
Villa in Cruz Bay
5 out of 5 average rating, 11 reviews

Maria Bluff Cottage Villa- Ocean Views, Generator,

This newer two-story cottage features ocean views, a private pool, and an exquisite kitchen. Ideal for a couple, small group, or family, it offers easy access from its private driveway. The cottage includes a full kitchen, living room, laundry area, coral stone deck, outdoor dining, plunge pool, and two bedrooms with en-suite bathrooms. Multiple zones of air conditioning ensure comfort for everyone in the group. This Villa has a generator that will automatically kick on if the power goes out so

Guest favorite
A private balcony features a glass-top table with two chairs, creating a cozy spot to enjoy the stunning view of the turquoise Caribbean waters and surrounding hills. Sailboats are seen anchored in the bay, enhancing the scenic coastal landscape.
Condo in Cruz Bay
4.8 out of 5 average rating, 114 reviews

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

Top guest favorite
Condo in East End
4.96 out of 5 average rating, 139 reviews

BEST REVIEWS on the East End - HANDS DOWN!

ALWAYS BOOK with an ON-SITE LOCAL to get the INSIDE SCOOP. Book this condo to gain access to custom-made handouts to help you plan a memorable vacation! You'll love the KILLER VIEW of the Caribbean Sea about 200 feet away. This condo includes toys and games, and plenty of beach toys, noodles, and extra chairs for beach hopping! I'm frequently booked, so check out my other condos in Cowpet Bay West. airbnb.com/h/stthomasparadise10 airbnb.com/h/stthomasparadise26 airbnb.com/h/stthomasparadise42

Top guest favorite
A wooden bench with a sign reading 'SAIL AWAY' is positioned on a patio, overlooking the vibrant blue waters of a beach. Lush green foliage and palm trees frame the view, with rolling hills visible in the distance under a partly cloudy sky.
Condo in East End
4.95 out of 5 average rating, 133 reviews

Sail Away II-WOW Beachfront to Paradise Remodeled

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. Golden sand, pristine 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. KING SIZE BED!

Guest favorite
A close-up view of several pink orchids is presented, featuring delicate petals with fine lines and a vibrant red and purple center. The background shows hints of greenery, with the arrangement of flowers suggesting a serene indoor setting.
Apartment in Saint John
4.93 out of 5 average rating, 135 reviews

Orchid at Casa Tre Fiori (Three Flowers House)

Casa Tre Fiori's Orchid is a large, private and peaceful one bedroom apartment with a large deck overlooking the labyrinth garden. There is a fully equipped kitchen and air-conditioned bedroom. Enjoy the sounds of nature from the deck. Walk to some of the National Park hiking trails. Easy 4 miles to town and short drive to North Shore beaches. Fish Bay is adjacent to the National Park on the south shore of the St John. The shared pool and hot tub are located nearby along the Zen Garden path.

Superhost
A panoramic view is presented at sunset, showcasing a vibrant sky filled with hues of orange, pink, and purple. The silhouette of distant islands can be seen against the reflective water, creating a serene atmosphere.
Condo in Cruz Bay
4.8 out of 5 average rating, 158 reviews

Sunset Villa Studio Condo at The Hills Saint John

You have to see Sunset Villa for yourself! Sunset Villa is a stunning one bedroom studio with kitchenette, in a gated community, offering resort like amenities with amazing views! You will have access to The Clubhouse bar and restaurant (open seasonally), the game room including a pool and ping pong table and big screen television, sunset terrace, and community pool. Sunset villa has a private entrance, king size bed, and large windows so you can take in the view. You will not be disappointed!

Guest favorite
Home in Cruz Bay
5 out of 5 average rating, 9 reviews

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!

Top guest favorite
An outdoor patio features tiled stones surrounding a small salt-system plunge pool. Two lounge chairs with cushions are positioned nearby, while lush green banana plants fill the background. A beige umbrella provides shade, and the sky is bright with scattered clouds.
Cottage in Coral Bay
4.99 out of 5 average rating, 142 reviews

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.

Top guest favorite
A bright living area features large windows that frame scenic mountain views. A light-colored sofa and two armchairs surround a wooden coffee table, complemented by a natural stone accent wall. Decorative plants add a touch of greenery, while a television is mounted on the wall.
Apartment in Cruz Bay
5 out of 5 average rating, 108 reviews

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.

Top guest favorite
A spacious pool area is highlighted by a refreshing private pool, surrounded by a wooden deck. Two black loungers provide comfortable seating, while colorful inflatables add a playful touch to the clear water. The setting is brightened by large glass doors and subtle outdoor lighting.
Home in East End
4.97 out of 5 average rating, 135 reviews

Private Pool in Paradise! Ocean View Steps 2 Beach

Come enjoy the island life at this tranquil villa with private pool...only steps from the beach! Cooler, snorkeling gear, and beach chairs INCLUDED! The entire home has been remodeled. The pool has been fully updated as well as the deck area, which includes brand new furniture and high-end loungers. A new gas grill has also been added for your outdoor grilling pleasure. Stream all your favorites with our strong Wi-Fi. Upscale restaurant, Pangea, is just steps away. Free parking.

Popular amenities for Cruz Bay rentals with a pool

When is the best time to visit Cruz Bay?

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Avg. priceﺩ.ﺇ2,898ﺩ.ﺇ2,824ﺩ.ﺇ2,798ﺩ.ﺇ2,552ﺩ.ﺇ2,145ﺩ.ﺇ2,112ﺩ.ﺇ2,259ﺩ.ﺇ2,295ﺩ.ﺇ2,123ﺩ.ﺇ2,079ﺩ.ﺇ2,218ﺩ.ﺇ2,776
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Quick stats about vacation rentals with a pool in Cruz Bay

  • Total vacation rentals

    Explore 490 vacation rentals in Cruz Bay

  • Nightly prices starting at

    Cruz Bay vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

  • Verified guest reviews

    Over 5,490 verified reviews to help you choose

  • Family-friendly vacation rentals

    360 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    480 of Cruz Bay vacation rentals include wi-fi 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!