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
4.8 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
Home in Cruz Bay
5 out of 5 average rating, 11 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 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.
Guesthouse in Saint Thomas
5 out of 5 average rating, 110 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.

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, 193 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
An outdoor seating area is showcased, featuring two cushioned armchairs and a wooden coffee table. The space offers views of lush greenery and a pool below, framed by a wrought iron railing. Bright skies and distant hills enhance the tranquil ambiance.
Apartment in Cruz Bay
4.99 out of 5 average rating, 177 reviews

Sieben Apartment * Pool* next to Hiking trails

Sieben is a spacious 2 bedroom, 2 bathroom apartment with fully equipped kitchen and washer/dryer. Both bedrooms feature memory foam mattresses. Primary bedroom has a king bed with private en-suite bathroom. Second bedroom can be set up as two twin beds or one king. Smart TV with Netflix and streaming apps (no cable). 10 min drive to Cruz Bay, restaurants, and grocery stores. 25 min drive to North Shore Beaches. 4 ft shared pool with two other apartments and shared BBQ by the pool.

Top guest favorite
Two glasses of rose wine are positioned on a granite bar, accompanied by vibrant pink bougainvillea flowers. The background features a scenic view of Cruz Bay, showcasing boats anchored in clear turquoise waters and lush green hills under a partly cloudy sky.
Condo in Cruz Bay
4.96 out of 5 average rating, 55 reviews

New! Island Therapy Studio - amazing views-St John

Island Therapy Contemporary Studio -sleeps 4 (king bed +queen sleeper sofa) in St. John. Excellent condition with modern furniture, AC, and tile floors. Expansive views of Cruz Bay, flat screen cable TV, internet, fully equipped kitchenette (coffee maker, microwave, small fridge, toaster, blender, single electric burner), washer/dryer. Enjoy island sunsets from the balcony deck with granite bar and chairs overlooking the islands. We fell in love with St John and know you will too.

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, 136 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
Condo in Cruz Bay
4.94 out of 5 average rating, 131 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 favorite
The spacious living area features two light-toned sofas arranged around a glass coffee table, with a cozy bean bag on the floor. Natural light enters through two well-sized windows, creating an airy ambiance complemented by a modern floor lamp and a potted plant.
Apartment in Charlotte Amalie
5 out of 5 average rating, 131 reviews

Chic 1 Bedroom Oasis with Designer Decor & Pool

Welcome to our impeccably designed oversized 1-bedroom apartment (+ queen size Murphy bed) a stylish retreat that promises an unforgettable stay in the heart of the historic district of Charlotte Amalie with its own plunge pool and deck. This apartment boasts a sophisticated ambiance, curated with the finest designer furnishings, decor and lighting as well as a custom kitchen. This is a perfect location to serve as the base to explore St. Thomas and the surrounding islands.

Guest favorite
Home in Cruz Bay
5 out of 5 average rating, 6 reviews

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.

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
4.97 out of 5 average rating, 65 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.

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!