Vacation 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 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
4.79 out of 5 average rating, 106 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
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, 133 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 favorite
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, 181 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 favorite
A wooden dining table with four matching chairs is elegantly set on a covered balcony. Bright pink bougainvillea flowers are arranged in a clear vase at the center. Beyond, a stunning view of boats dotting the azure waters and green hills is visible.
Condo in Cruz Bay
4.99 out of 5 average rating, 69 reviews

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. 



Top guest favorite
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 favorite
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 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, 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 favorite
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 favorite
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.

Guest favorite
Two vibrant turquoise Adirondack chairs are positioned on a wooden deck, overlooking calm azure waters. The view extends toward distant green hills under a partly cloudy sky, creating a serene coastal atmosphere.
Guest suite in Cruz Bay
4.96 out of 5 average rating, 48 reviews

Oceanfront - Perfect couple only romantic getaway

We are Rendezvous by the Sea - A perfect couple's only romantic getaway. We have two separate guest rooms with their own private entrance and patio area. They are in a separate building away from the main villa where the owners and host live. This is our lower unit, we call Le Jardin. The view from your outdoor seating area overlooking the bay is breathtaking. We have our own path to a private pebble/coral beach below. We are only 10 minute drive to Cruz Bay.

Guest favorite
Aerial view captures the resort's layout alongside a serene bay, with clear blue waters and anchored boats. Lush palm trees frame a central pool area, enhancing the landscape and guiding the eye towards the sandy beach and distant hills under a partly cloudy sky.
Villa in Cruz Bay
4.96 out of 5 average rating, 25 reviews

Ring in Spring at the Westin St. John!

From the Westin's website: Amid active days exploring St. John's pristine beaches and relaxing days taking in your own piece of paradise at the resort, you'll revel in coming back here. A short walk or drive will take you to some of the most pristine beaches in the world. After hours of exploring the coastline snorkeling, swimming and enjoying life to the fullest, you’ll enjoy the resort’s spectacular quarter-acre pool, restaurants, activity programs and more.

Top guest favorite
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, 91 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.

Popular amenities for Cruz Bay rentals with a pool

When is the best time to visit Cruz Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$165,191 GYDG$161,003 GYDG$159,538 GYDG$145,510 GYDG$122,270 GYDG$120,386 GYDG$128,761 GYDG$130,854 GYDG$121,014 GYDG$115,152 GYDG$123,527 GYDG$151,582 GYD
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Quick stats about vacation rentals with a pool in Cruz Bay

  • Total vacation rentals

    Explore 480 vacation rentals in Cruz Bay

  • Nightly prices starting at

    Cruz Bay vacation rentals start at G$4,187 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    350 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wi-Fi availability

    470 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!