
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.

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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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
House rentals with a pool

Down Yonder Pool Villa / Full Solar & Battery

* 3BR/3 BA LUX Pool Villa*Cruz Bay*Amazing Views

2 Bed ⭐️ STAR VILLA HOME ⭐️ 5 Min walk to CRUZ BAY

Oceanfront Private Caribbean Resort!

Mar de Amores - Winter deals!

Luxury Villa with Pool, Privacy, Sunsets

Spectacular Views - 3-5 bedrooms Cruz Bay, St John

Texas Embassy
Condo rentals with a pool

Charming Beach Condo w/ Balcony- 2 Pools and Beach

BEST REVIEWS on the East End - HANDS DOWN!

Seas The View-Updated & Oceanview @ Sapphire Beach

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

VIEWS! Condo by Magen's Beach w/ POOL & generator!

Sail Away II-WOW Beachfront to Paradise Remodeled

Wrap Around Balcony~Views~Pack your Bathing Suit!

Beachfront • King • W/D • By RH • Pool • Marina
Other vacation rentals with a pool

Elysium Villa-Natural Surroundings, Ocean Views, P

Milk Moon Cottage

Villa Hermosa - Beautiful with Pool & Ocean Views

Condo with Northside Views & Back-Up Generator

A House of Open Arms Villa with Pool and AC

SOLAR! Gorgeous views from every room, Pool, A/C

Cruz Bay Getaway! One bedroom apt & Sunset views

Tropical Breeze: Comfortable Downtown Vacationing
When is the best time to visit Cruz Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$165,191 GYD | G$161,003 GYD | G$159,538 GYD | G$145,510 GYD | G$122,270 GYD | G$120,386 GYD | G$128,761 GYD | G$130,854 GYD | G$121,014 GYD | G$115,152 GYD | G$123,527 GYD | G$151,582 GYD |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°C |
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!
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