
Cruz Bay Rentals
- From $1245 per night (USD)
VRBO
BlueWater Vista - MAGNIFICENT VIEWS!!! Safe, family friendly villa close to town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
BlueWater Vista a 4 bedroom / 3 1/2 bath turnkey pool villa located in Chocolate Hole, very close to downtown Cruz Bay. ...
From $1245 per night (USD)VRBO
- From $1038 per night (USD)
VRBO
Oceanport Villa : Great location, stunning views with pool and spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront 4BR home with amazing views!!! 220 Stone steps lead down to Hart Bay beach where you can explore or clamber ...
From $1038 per night (USD)VRBO
- From $2010 per night (USD)
VRBO
Beachfront-Jacuzzi, Kayaks, SUPs, Snorkel Gr, No Stairs, Close to Town-GENERATOR
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Beach Oasis Villa -For The Ultimate Beachfront Luxury on St. John On the beach, steps to the sea-in calm Chocolate Hole ...
From $2010 per night (USD)VRBO
- From $412 per night (USD)
Expedia
Livin' the Dream 1BR Suite Grande Bay in Cruz Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Condo, 1 Bedroom + Convertible bed(s), 1 Bath, (Sleeps 2-4) We are proud to offer you a professionally designed and dec ...
From $412 per night (USD)Expedia
- From $793 per night (USD)
VRBO
Gallows Point 3A-Luxury oceanfront lower 1 BR condo at Gallows Point Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
One Bedroom, one bath oceanfront Condo at St. John's finest Resort Hotel. This 750 square foot condo is located steps f ...
From $793 per night (USD)VRBO
- From $2004 per night (USD)
VRBO
Beachfront, HEATED Pool, Spa, Snorkel gear, Kayaks, SUPs, Near Town-GENERATOR
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
SHANGRI-LA VILLA-For The Ultimate Beachfront Luxury on St. John Direct Beachfront | Heated Infinity Pool | Large Jetted ...
From $2004 per night (USD)VRBO
- From $918 per night (USD)
VRBO
Amazing large penthouse. Walk to town. Pool. Breathtaking views. Luxury.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom, 3 Bath, 2 Large Balconies, Sleeps 6 Blue Coral is a magnificent, luxury 3 bedroom, 3 bath condo villa with s ...
From $918 per night (USD)VRBO
- From $358 per night (USD)
Expedia
Breezy Hilltop, Hart Bay View, only minutes from town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our hilltop, chocolate hole location provides fantastic ocean views and the southern exposure catches the cooling trade- ...
From $358 per night (USD)Expedia
- From $4823 per night (USD)
VRBO
Exclusive Sunset Villa Beautiful private Caribbean estate home on Great Cruz Bay
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Sunset Villa is a captivating beautiful newly renovated private Caribbean Villa resort home located in picturesque Great ...
From $4823 per night (USD)VRBO
- From $902 per night (USD)
Expedia
Sopra Mare: Oceanfront, Heated Saltwater Pool, 100% A/C, Endless Views, More...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perched 150' above the Caribbean Sea you will enjoy sweeping ocean views from most rooms in your oceanfront 2 bedroom 2. ...
From $902 per night (USD)Expedia
- From $829 per night (USD)
VRBO
Idyllic Villa - Great Pool and deck areas, great family home, A/C throughout
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Property may be shown to prospective renters with 24 hour notice to show. If your dates are pre-approved - you must pay ...
From $829 per night (USD)VRBO
- Click For Pricing
Expedia
Family Friendly 3BR Villa in Paradise- Saturday March 26- Sat., April 4, 2026
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Unit available 3/26-4/4/26 Enjoy this spacious 3BR/3BA unit within steps of the ocean. Giant pool and on site restauran ...
Click For PricingExpedia
- From $783 per night (USD)
VRBO
Pink Conch - 2 Bedroom Luxury Villa, Great Cruz Bay, St. John - Backup generator
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 4
Pink Conch is a 2 bedroom luxury vacation villa located along The southeastern facing shoreline of Great Cruz Bay, overl ...
From $783 per night (USD)VRBO
- From $558 per night (USD)
VRBO
Jungle Love!, Private, Romantic Eco-Luxury Cottage, Hot Tub, Kayaks, Cabana
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
COCONUT COTTAGE Romantic Hillside Jungle Oasis | Private Hot Tub Grotto | Bay Views | Walk to Chocolate Hole Beach I Ge ...
From $558 per night (USD)VRBO
- From $490 per night (USD)
VRBO
Grande Bay LOVE CITY PENTHOUSE studio, Great Views, WIFI, Beachfront Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Great view of Cruz Bay Harbor. Love City Penthouse Studio is the perfect escape. You will have breathtaking views of not ...
From $490 per night (USD)VRBO
- From $776 per night (USD)
VRBO
Bongo Bongo - St. John's Coolest Two Bedroom Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bongo Bongo, a two-bedroom all air-conditioned St. John vacation villa in upscale Chocolate Hole North, just five minute ...
From $776 per night (USD)VRBO
- From $874 per night (USD)
VRBO
Newly Remodeled-Waterfront-4 King Suites-WHOLE HOUSE A/C-Full Solar&Tesla Backup
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Southern Cross Villa has undergone a complete renovation—every surface, furnishing, and detail has been refreshed! Full ...
From $874 per night (USD)VRBO
- From $995 per night (USD)
VRBO
Water access to Great Cruz Bay with pool! Solar back-up power!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
LOCATION, location, location! This listing is for the UPPER LEVEL of, PEACE OF CHOCOLATE, a 2-story villa with a pool l ...
From $995 per night (USD)VRBO
- From $541 per night (USD)
VRBO
This exceptional property offers the convenience of being just a short stroll from Cruz Bay, all while providing the comfort of full air conditioning. Don't miss out on this perfect blend of location and luxury!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lavender Hill Windcatcher 5W – Romantic Ocean View Condo in Cruz Bay, St. John Discover the charm of Lavender Hill Wind ...
From $541 per night (USD)VRBO
- Click For Pricing
Expedia
Gorgeous Oceanfront Westin St. John Spacious Deluxe Studio at Huge Discount
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Westin St. John Resort & Villas has been rated among the Top 10 Caribbean Resorts for families by Travel and Leisure Mag ...
Click For PricingExpedia
- From $1133 per night (USD)
VRBO
Virgin Grand Two Bedroom Villa at the Westin St. John
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at Westin St. John Villas, Virgin Grand We are able to offer 7 night ...
From $1133 per night (USD)VRBO
- From $896 per night (USD)
VRBO
Luxury-Steps to Sea, Jacuzzi,Kayaks,Paddle Boards,Snorkeling gear, Close to Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
POSEIDON'S RETREAT Just Steps Away To The Beach/Sea l | Sea Views | 3 King Suites Imagine stepping out your door, layin ...
From $896 per night (USD)VRBO
- From $1020 per night (USD)
VRBO
Villa Splendore: The Ideal Getaway with Pool, Spa, A/C, and Close to All Cruz Bay Has to Offer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Splendore – Beautiful 3-Bedroom St. John Villa with Caribbean Views, Pool, and Hot Tub Villa Splendore is a stunn ...
From $1020 per night (USD)VRBO
- From $317 per night (USD)
Expedia
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to your own tropical paradise! This stunning 2-bedroom, 2-bathroom villa is located on a quiet road just steps fr ...
From $317 per night (USD)Expedia
- From $558 per night (USD)
VRBO
Happy Does- 1 BR Grande Bay Unit with Stunning Views of Cruz Bay! Walk to town!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Happy Does is a one bedroom unit at Grande Bay Resort. All of the amenities of Grande Bay are at your finger tips! This ...
From $558 per night (USD)VRBO
- From $936 per night (USD)
Expedia
Hale Lani Villa - breathtaking views Tesla backup power
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Hale Lani Villa has beautiful ocean and sunset views! Close to Cruz Bay town (10 minutes) and National Park beaches (15 ...
From $936 per night (USD)Expedia
- From $1190 per night (USD)
VRBO
Cool Change Villa- Luxury Villa with Lush Landscaping & updated/modern amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cool Change Villa is new to the rental market! This 3 bedroom property is located just past the Westin in Chocolate Hole ...
From $1190 per night (USD)VRBO
- From $1552 per night (USD)
Expedia
ALTAMIRA - Big Blue Caribbean Ocean Views with Private Pool and Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
With massive blue ocean views from every angle and fresh Caribbean tradewinds wisping through the property, this newly r ...
From $1552 per night (USD)Expedia
- From $1070 per night (USD)
VRBO
Best Views of Chocolate Hole - 5 mins from Cruz Bay - Solar with battery backup
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Renting the entire villa (5 bedrooms/sleeps 10 comfortably) This property has 2 beautifully appointed areas; giving yo ...
From $1070 per night (USD)VRBO
- From $643 per night (USD)
Expedia
\"Pristine 2bdrm/2bth, Epic Views, Generator, 5 Star reviews, Near Cruz Bay!\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
"Welcome to the "Sweet St. John 2 !" It is an immaculate 2 bedroom, 2 bath Luxury Cottage with breathtaking westerly su ...
From $643 per night (USD)Expedia
- From $1795 per night (USD)
VRBO
Westin St John luxury 2 Bedroom Villa Sunset Bay - pool or oceanfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Indulge in paradise at the Westin St John! Your 2-bedroom villa in the Sunset Bay phase promises the prime pool and beac ...
From $1795 per night (USD)VRBO
- From $403 per night (USD)
Expedia
Ocean Views · Walk to Cruz Bay · Beach Ready
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Wake up to ocean views and unwind on the spacious screened porch with relaxing porch swings overlooking the Caribbean. P ...
From $403 per night (USD)Expedia
- From $2446 per night (USD)
VRBO
2 Westin Sunset Bay Villas Beachfront Resort & Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to the Great Cruz Bay of St. John at the Westin St. John's newest development - the Sunset Bay Villas! The Sunset ...
From $2446 per night (USD)VRBO
- From $1886 per night (USD)
Expedia
Villa Royce -Defining Luxury-Pool-Tesla backup power!!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Villa Royce is located in Cruz bay on the Contant point peninsula and overlooks Great Cruz bay. This 4 bedroom 4 and hal ...
From $1886 per night (USD)Expedia
- From $1330 per night (USD)
VRBO
2 Bay Vista Villas Beachfront Resort & Spa, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The Westin St John is a 47-acre tropical paradise on the shores of Great Cruz Bay. Crystal waters and temperate climate ...
From $1330 per night (USD)VRBO
- From $496 per night (USD)
Expedia
Edgewater Villas-Studio Unit-Central easy walking location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Edgewater Villas; Is a modern luxury studio & waterfront property; pool overlooking car ferry harbor and Turner Bay, un ...
From $496 per night (USD)Expedia
- From $437 per night (USD)
VRBO
New rental, Newly Renovated 3br/2ba - open main room/beautiful view/large pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the newly renovated and newly available Villa St. Somewhere, now on the rental market for the first time! Nest ...
From $437 per night (USD)VRBO
- From $1181 per night (USD)
VRBO
Beyond the Sea - Waterfront/cliffside Villa, A/C, Generator - Sunsets amazing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beyond the Sea - is exactly what you will see!!! Walk into your vacation dream home. Every inch of this property has b ...
From $1181 per night (USD)VRBO
- From $431 per night (USD)
VRBO
Conch Villa Vista! Amazing Ocean Views!! 2 Bed 1 Bath Condo in Cruz Bay Sleep 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Conch Villa Vista condo is a dream with outstanding views of the Caribbean Sea! Located in Cruz Bay and within walking ...
From $431 per night (USD)VRBO
- From $754 per night (USD)
VRBO
New Modern 2 bedrooms, 2 bath Grand Opening Special, 10 min easywalk to Cruz Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover this lovely new 2-bedroom gem in Urban Cruz Bay. This property offers private suites with private balconies and ...
From $754 per night (USD)VRBO
- From $682 per night (USD)
VRBO
A beautifully updated 1-bedroom condo just a short stroll from the vibrant Cruz Bay. Embrace modern living in a prime location that offers both convenience and comfort.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Lavender Hill – Rumm Lime 7E | Renovated 1-Bedroom Condo with Harbor Views in Cruz Bay, St. John Welcome to La ...
From $682 per night (USD)VRBO
- From $327 per night (USD)
Expedia
Anestasi Cottage Brand new charming cottage with water views close to Cruz Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located in Chocolate Hole area of Cruz Bay, this peaceful cottage is a dream. Quiet neighborhood location walking distan ...
From $327 per night (USD)Expedia
- From $800 per night (USD)
VRBO
Frank Bay House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
UNPARALLELED VIEWS & ISLAND LIVING AT ITS BEST! WALK TO CRUZ BAY – CLOSE TO EVERYTHING – AND TUCKED AWAY ON A QUIET LANE ...
From $800 per night (USD)VRBO
- From $1041 per night (USD)
Expedia
Experience the exquisite Mango Serenity, a spacious condo that offers breathtaking views and an abundance of comfort. Discover your perfect getaway today!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Upscale Penthouse Condo in St. John with Ocean Views Near Cruz Bay Experience the perfect blend of luxury, comfort, and ...
From $1041 per night (USD)Expedia
- From $733 per night (USD)
VRBO
Nautilus- Beach Front with 3 King Suites
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Nautilus Villa is brand-new, spacious, and beach front! This luxurious 3-bedroom villa features breathtaking ...
From $733 per night (USD)VRBO
- From $685 per night (USD)
Expedia
Serenity Villa- Steps from Beach, Family Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Serenity Villa, a brand-new, spacious, and inviting beachfront retreat! This luxurious 3-bedroom vi ...
From $685 per night (USD)Expedia
- From $843 per night (USD)
VRBO
Bordo Mare: Oceanfront, Heated Saltwater Pool, 100% A/C, Endless Views, More...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perched 100' above the Caribbean Sea you will enjoy sweeping ocean views from every room in your oceanfront 2 bedroom 2. ...
From $843 per night (USD)VRBO
- From $2184 per night (USD)
Expedia
Villa Sol Mate! New 4 Bedroom!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Villa Sol Mate is new to the vacation rental market. Located ocean front in Great Cruz bay providing great access to the ...
From $2184 per night (USD)Expedia
- From $1085 per night (USD)
VRBO
Exclusive Luxury 2BR Bay Vista / Westin St John Resort / Thanksgiving Week
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Nestled in Cruz Bay, this delightful resort offers guests a cool retreat with two comfortable bedrooms featuring a king ...
From $1085 per night (USD)VRBO
- From $3775 per night (USD)
VRBO
4BDR/6 BA The Westin St. John-Virgin Grand Villas
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 12
Two-thirds national park, the tiny island of St. John is home to virgin forests, hiking trails, an underwater snorkeling ...
From $3775 per night (USD)VRBO
- From $1774 per night (USD)
VRBO
NEW! Dreamy & Spacious 5-bedroom house with generator in Cruz Bay with Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to one of the most sought‑after destinations in the Caribbean—St. John, home to the world‑renowned Trunk Bay. Thi ...
From $1774 per night (USD)VRBO
- From $970 per night (USD)
VRBO
The Edgewater Penthouse suite is a Modern Luxury in delightful Cruz Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Cruz Bay, enjoy this beautiful Penthouse-1 bedroom king Bed($150 for extra bed per advanced request ) , 1 & ...
From $970 per night (USD)VRBO
- From $1571 per night (USD)
VRBO
Perfect 4 Equal-Bedroom Villa in serene Cruz Bay with Private Pool, A/C & Solar!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
One of St John's most popular rental homes, this 4-bedroom Villa is perfect for your escape. Each bedroom is identical, ...
From $1571 per night (USD)VRBO
- From $729 per night (USD)
Expedia
At the Beach Villa, Beachfront, Kayaks & SUPs
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Wake Up to Chocolate Hole Bay — Beachfront Villa Step outside to calm turquoise water and a private stretch o ...
From $729 per night (USD)Expedia
- From $1431 per night (USD)
VRBO
Westin St John 3 Bedroom Pool Villa - Full Resort Access - Late Apr/Early May
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Westin St John 3 Bedroom Pool Villa w/ Hot Tub - Full Resort Access! The Westin St John Resort & Villas is a Luxury pro ...
From $1431 per night (USD)VRBO
- From $752 per night (USD)
Expedia
Mahalo Villa, Beachfront, Generator
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: A rare beachfront retreat, Mahalo Villa is located in Pond Bay, Chocolate Hole, just minutes from Cruz Bay. Se ...
From $752 per night (USD)Expedia
- From $1995 per night (USD)
VRBO
Westin's Gorgeous Beachfront Resort + Resort Amenities Included. 3-Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Book with Chairman owners! This breathtaking beachfront resort in St. John is perfect for your Caribbean escape. Access ...
From $1995 per night (USD)VRBO
- From $1183 per night (USD)
Expedia
3 Bedroom Virgin Grand Villa - Private Pool, Westin St John Nov 29 - Dec 6, 2026
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Westin St. John Resort & Villas is a scenic property situated on the tiny island of St. John, home to virgin forests, hi ...
From $1183 per night (USD)Expedia
- From $6356 per night (USD)
VRBO
NEWLY BUILT Luxury Villa in the Heart of Cruz Bay
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Rock is a European-inspired architectural masterpiece located in the heart of Cruz Bay — just a three-minute walk i ...
From $6356 per night (USD)VRBO
- From $1028 per night (USD)
VRBO
Incredible Beachfront Cruz Bay Resort + Amenities Included. 2-Bedroom Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Book with Chairman owners! This breathtaking beachfront resort in St. John is perfect for your Caribbean escape. Access ...
From $1028 per night (USD)VRBO
- From $791 per night (USD)
VRBO
Stunning 2BR Hillside Sunset Villa - Westin St. John Virgin Grand
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
The Westin St John Villas are located in a highly sought-after destination with visitors from across the globe. The isl ...
From $791 per night (USD)VRBO
- From $1701 per night (USD)
VRBO
NEW! Ultra Luxury 3 Bedroom Pool Villa at the Westin St. John!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Vacation in ultimate luxury in this 3 bedroom private pool villa at the prestigious Westin St. John Resort! 2800 sqft of ...
From $1701 per night (USD)VRBO
- From $1686 per night (USD)
VRBO
NEW! Sunset Bay 2 Bedroom Villa - Westin St. John - Right beside the ocean!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The 2 bedroom Sunset Bay villas are the ultimate space to vacation in at the Westin St. John - just steps from the ocean ...
From $1686 per night (USD)VRBO
- From $1686 per night (USD)
VRBO
NEW! Ultra Luxury 2 Bedroom Villa at The Westin St. John - Resort Side!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Luxurious waterfront vacation at the Westin St. John! Located in Great Cruz Bay, this resort is a dream for guests looki ...
From $1686 per night (USD)VRBO
































































