Holiday rentals with a pool in Cruz Bay

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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
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
4.79 out of 5 average rating, 107 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 favourite
A sandy beach offers a serene view featuring clusters of leafy trees providing shade. The calm turquoise waters are visible in the background under a clear blue sky. Beach seating is scattered along the shoreline, inviting relaxation and enjoyment of the landscape.
Condo in East End
5 out of 5 average rating, 193 reviews

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

"H2Oh What a Beach!" condo Building A of Sapphire Beach Resort & Marina: ground floor unit with direct access to one of the most beautiful beaches in the Caribbean. Steps away from Sea Salt fine dining restaurant, Sapphire Beach Bar, Paradise Pie pizza, and Beach Buzz coffee shop. A mile from Red Hook featuring many restaurants & island ferries. Great beach, swimming, snorkeling, parasailing, and relaxing right outside your door. Be among the many visitors who LOVE this totally renovated condo.

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, 134 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.

Guest favourite
A cluster of white jasmine flowers blooms amidst lush green leaves. The delicate petals are arranged symmetrically, creating an inviting contrast against the vibrant foliage.
Apartment in Fish Bay
4.93 out of 5 average rating, 182 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.

Top Guest favourite
A tranquil pool area features a glistening pool surrounded by a tiled deck. Two wooden lounge chairs and several sun loungers are positioned nearby, complemented by a textured stone wall adorned with green plants. The setting invites relaxation in a serene environment.
Apartment in Cruz Bay
5 out of 5 average rating, 120 reviews

Skytop Studio~Next to Hiking Trail~New Pool

Modern 1 bedroom apartment In Fish Bay Skytop with Hillside View of the National Park, fully equipped kitchen, Saatva Loom & Leaf memory foam mattress. The property is right next to the National Park Great Sieben Trail, which connects to several major hiking trails. Cruz Bay, Grocery Stores and restaurants are 12min drive away. Klein Bay a beautiful Private rocky beach great for snorkeling is 4 min drive away. Shared brand new Pool with two other apartments. Shared BBQ by the Pool.

Top Guest favourite
Condo in Cruz Bay
4.94 out of 5 average rating, 119 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 Bistro (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

Top Guest favourite
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, 120 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.

Top Guest favourite
A serene pool area is surrounded by lounge chairs and lush greenery, offering a refreshing space for relaxation. The modern villa structure features a light color scheme and large windows, allowing for ample natural light and views of the landscape.
Home in Cruz Bay
4.97 out of 5 average rating, 30 reviews

Windchime-Gorgeous View, Pool, Generator-Sleeps 10

The name says it all. Windchime Villa is perched high on the mountains of St. John, with panoramic views to the east. Newly renovated, Windchime Villa offers a unique blend of privacy and seclusion and is just 7 minutes to the shops, restaurants, and town of Cruz Bay. The home features extensive outdoor areas, a large refreshing pool, and a versatile bedroom configuration that would work for multiple couples or families. Forget your worries in this spacious and serene villa.

Top Guest favourite
A panoramic view of the Caribbean Sea is visible, with vibrant blue waters and gentle waves lapping against the shore. Lush greenery and a solitary palm tree frame the scene, enhancing the natural beauty of Hart Bay under a clear sky with scattered clouds.
Home in Cruz Bay
4.98 out of 5 average rating, 57 reviews

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.

Top Guest favourite
An inviting infinity pool is surrounded by tropical greenery, offering serene views of the landscape. Spacious stone steps lead to the pool edge, where loungers are positioned nearby. The sky above is dotted with fluffy clouds, enhancing the sense of tranquility in this outdoor retreat.
Villa in Cruz Bay
4.93 out of 5 average rating, 56 reviews

Charming 2 Bed 2 Bath Villa with Infinity Pool

Welcome to Perelandra Villa, a 2-bedroom, 2-bath haven, featuring its own secluded infinity pool. Set amid vibrant greenery punctuated by vivid, aromatic blooms, this residence promises a serene ambiance for all guests. From the elevated deck to the invigorating pool, indulge in mesmerizing views of azure seas and Cruz Bay. Come dusk, capture the allure of the sunset, painting vivid Caribbean hues across the sky.

Guest favourite
A light-filled living area features a spacious white sofa paired with a geometric wooden coffee table. An open dining space with a wooden table and chairs can be seen in the background, while large sliding doors invite natural light and offer easy access to the outdoors.
Holiday home in Saint Thomas
4.92 out of 5 average rating, 169 reviews

Villa La Realeza - Award Winning Design - VIEWS!

Welcome to Villa La Realeza by Virgin Islands Vacation. This Villa is the perfect island vacation rental in St Thomas, and is located inside the guard gated Point Pleasant Resort. The Villa offers the perfect blend of relaxation & adventure. Relax by the pools or simply enjoy amazing views from the private wrap around patio with views of St John & Tortola islands. NO PETS allowed, $250 fee if violated.

Guest favourite
An infinity pool stretches towards the horizon, overlooking lush green hills and distant islands. Lounge chairs are arranged along the poolside, complemented by a turquoise float. The covered terrace provides a shaded seating area, with panoramic views under a sky painted with soft clouds.
Apartment in Cruz Bay
4.9 out of 5 average rating, 39 reviews

NEW Spacious 3 bed villa w/t Pool & Ocean View

Bring the entire family to this quite neighborhood, a great place with lots of room for sun and fun with a large private pool and a gorgeous view of St. John Harbor. Lounge chairs and beach towels included. 4x4 4Door Wrangler & Ford Branco are available to rent exclusive to guests! Please note the house is located on a steep incline which means a 4x4 vehicle is highly recommended

Popular amenities for Cruz Bay rentals with a pool

When is the best time to visit Cruz Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$1,179 AUD$1,149 AUD$1,138 AUD$1,038 AUD$873 AUD$859 AUD$919 AUD$934 AUD$864 AUD$822 AUD$882 AUD$1,082 AUD
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Quick stats about holiday rentals with a pool in Cruz Bay

  • Total holiday rentals

    Explore 480 holiday rentals in Cruz Bay

  • Nightly prices starting at

    Cruz Bay holiday rentals start at $30 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    350 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wi-Fi availability

    470 of Cruz Bay holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Cruz Bay rentals

  • 4.9 Average rating

    Cruz Bay stays are highly rated by guests—averaging 4.9 out of 5!