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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.

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Guest favourite
Apartment in Cruz Bay
4.81 out of 5 average rating, 120 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

Guest favourite
A serene view of turquoise waters stretches to the horizon, with a sailboat gently anchored in the foreground. The surrounding landscape includes green vegetation and a clear blue sky dotted with soft clouds, providing a tranquil backdrop to the scene.
Home in Cruz Bay
4.89 out of 5 average rating, 56 reviews

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. 💕

Top guest favourite
Apartment
4.93 out of 5 average rating, 113 reviews

Wrap Around Balcony w/Amazing Views! Remodeled!

Book Now! Down Island Dream is a 1BR/1BA luxury villa located @Point Pleasant on the East End of St Thomas. 2 Restaurants, 3 pools, nature trail & small intimate beach to enjoy. Your vacation home/5 minutes to Red Hook w/shops, bars, restaurants & the ferry to St John where you can explore, hike & enjoy our National Park Beaches! 3 mins to Lindquist & Coki beaches. Amazing views & refreshing breezes await you at Down Island Dream! Try our home away from home for the week & fall in love!

Top guest favourite
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, 156 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 favourite
A private infinity pool is situated on a terrace, overlooking lush greenery and a panoramic ocean view. A vibrant rainbow arcs across the horizon, while gentle waves suggest a tranquil atmosphere. The pool's edge blends seamlessly with the surrounding landscape.
Guest house in Saint Thomas
5.0 out of 5 average rating, 117 reviews

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.

Top guest favourite
Apartment in Cruz Bay
4.93 out of 5 average rating, 147 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 Bar (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

Top guest favourite
A vibrant red ginger flower stands tall amidst lush green foliage, showcasing intricate layers of petal-like bracts. The natural lighting enhances its striking color, creating a vivid focal point within the tranquil garden setting.
Home in Cruz Bay
4.99 out of 5 average rating, 100 reviews

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.

Guest favourite
The cottage is set within a vibrant garden, with lush tropical plants and colorful shrubs surrounding the property. Tall palms provide shade, while a covered patio is visible through the greenery. A gated entrance adds a sense of privacy to the peaceful setting.
Cottage in Cruz Bay
4.93 out of 5 average rating, 41 reviews

Seabreeze Cottage with private pool in Cruz bay

The cottage is conveniently located two minutes to the town of Cruz bay and five minutes to National Park. It’s surrounded by lush landscape and gated property. The cottage is fully AC, covered patio, a private pool, outdoor bbq covered patio. AN ENTIRE COTTAGE BACK UP GENERATOR FOR POWER OUTAGES one of a few offer on the island. It will be helpful when the grid goes down of which occurs quite often. You can still have the comfort without any interruption.

Top guest favourite
A charming studio home, surrounded by lush greenery, features a welcoming porch with steps leading to the entrance. Stone pathways are lined with various plants, complemented by seating areas designed for relaxation. The building is highlighted by large windows that invite natural light.
Cottage in Cruz Bay
4.98 out of 5 average rating, 111 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.

Top guest favourite
An aerial view of a contemporary home reveals a red roof and an infinity pool lined with lounge chairs. Surrounding greenery enhances the sense of privacy, while a spacious driveway provides easy access. Large windows allow for plenty of natural light to enter the interior.
Villa in Charlotte Amalie
4.99 out of 5 average rating, 103 reviews

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.

Guest favourite
A panoramic view of the ocean displays various boats anchored in the crystal-clear blue water. Overlapping shades of turquoise enhance the serene landscape, with distant hills creating a natural frame against the clear sky. An area of red-roofed buildings is visible in the foreground.
Villa in Cruz Bay
4.93 out of 5 average rating, 30 reviews

Gorgeous ocean view penthouse! Walk to Cruz Bay!

Welcome to Palm Breeze Villa! This penthouse sits at the top of Battery Hill providing 360 degree views of the ocean and lush green hillsides. The covered deck provides much needed shade and beautiful ocean views of Cruz Bay. You can marvel at the multiple shades of the crystal clear blue water as you enjoy a morning cup of coffee or cocktail at sunset. You will be right in town so can easily walk to all your favorite restaurants and shops!

Top guest favourite
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.
Flat in Cruz Bay
5.0 out of 5 average rating, 126 reviews

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.

Popular amenities for Cruz Bay rentals with a pool

When is the best time to visit Cruz Bay?

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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
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