50 Best Cruz Bay Villas on Holiday Lettings - Vacation rentals

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94 Vacation rentals

(3) Excellent 

29

Vacation villa in Cruz Bay

St. John / Cruz Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
BEST VALUE ON ST JOHN! 3 BR 3BA Million Dollar Views!!! Built in the classic Caribbean style, Blue Heaven Rendezvous has million dollar views for the budget conscious travelers. All three Master Suites are air conditioned and have full baths for your comf …see more

from $225 / night

$1575 - $4375 / week

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from $225 / night

11

Vacation villa rental

St. John / Cruz Bay

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
NOW ACCEPTING RESERVATIONS FOR 2017. THE WESTIN ST. JOHN 3BR POOL VILLAS ARE TIMESHARE PROPERTIES OWNED FOR SPECIFIC WEEKS. WE OWN 4 WEEKS. OUR VILLA IS AVAILABLE ONLY THESE 2017 WEEKS! Rental availability below as of April 7, 2017 Week 30: 07/23/17 to 07/30/17 $ 4,9 …see more

from $715 / night

$4999 - $11999 / week

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from $715 / night

(9) Very Good 

14

Vacation villa with swimming pool in Cruz Bay

St. John / Cruz Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Nestled in an exclusive neighbourhood, this beautiful home offers comfort and privacy. Located in the hills above Chocolate Hole Bay, on the west side of St John, Catalina provides amazing views that includes St Croix, Rendezvous Bay, Hart Bay and Chocolate Hole. …see more

from $290 / night

$2000 - $4550 / week

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from $290 / night

(13) Very Good 

30

Vacation apartment with shared pool in Cruz Bay

St. John / Cruz Bay

1 5 5 nights min

  • 1 bedroom
  • Sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“Petit Tre’sor” (a small treasure) at Cruz Bay Villas is a charming one-bedroom condo located only a 10-minute walk from Cruz Bay and yet high on the side of a hill overlooking Pillsbury Sound to St Thomas. Unit #3 is situated just perfectly to enjoy the adjacent 20' x …see more

from $169 / night

$1183 / week

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from $169 / night

(5) Excellent 

24

Vacation villa in Cruz Bay

St. John / Cruz Bay

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Located on Gifft Hill, 750 feet above sea level, Coconuts features a unique combination of panoramic ocean views, spectacular sunsets, extensive outdoor living and dining areas, and numerous high-end amenities. The ocean views are among the finest on St. John, and inclu …see more

from $400 / night

$2800 - $6201 / week

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from $400 / night

20

Vacation home rental

St. John / Cruz Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.08 mi
  • Child friendly
Stardust is a charming Caribbean cottage in a perfect setting for a romantic getaway. Surrounded by lush landscaping, its arches, and gingerbread give the house a distinctly tropical feel. The interior layout is open and airy. The main floor offers three sets of dou …see more

from $200 / night

$1350 - $3301 / week

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from $200 / night

26

Vacation apartment with shared pool in Cruz Bay

St. John / Cruz Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Enter Blue Coral Condo up a short stairway from the private parking area located along the street in front of the building.  The entry door leads through the foyer and into the spacious and wonderfully furnished great room where you will be instantly amazed by the spect …see more

from $425 / night

$2976 - $4375 / week

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from $425 / night

(1) Excellent 

18

Vacation villa in Cruz Bay

St. John / Cruz Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
L'Esprit De La Vie L'Esprit is a perfectly appointed, beautiful home with breathtaking views from every room, patio and even showers! Features: • 4 large suites - king beds & on-suite bath! • Spacious deck/patio • Landscaped garden • Great room / dining / kitchen • WIFi …see more

from $720 / night

$5040 / week

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from $720 / night

(1) Excellent 

19

Cruz Bay Vacation apartment rental

St. John / Cruz Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Welcome! We have 7 units in Cruz Bay that each accommodate 2 people. We have 3 studio apts in Wharfside Village at the ferry dock. We have 4 units 1 mile from the ferry dock~ 2 studios in a luxurious gated community that overlook Cruz Bay and St. Thomas (gorgeous sun …see more

from $150 / night

$1050 / week

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from $150 / night

(16) Very Good 

26

Vacation villa with swimming pool in Cruz Bay

St. John / Cruz Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Amazing ocean views from every room at Villa Mar de Amores. Enjoy the Caribbean breezes at this spectacular family house at the top of Rock Ridge Road, in Chocolate Hole North; only 5 minutes away from town and shops. 3 bedrooms, 2 bathrooms, pool and a marvelous balcon …see more

from $340 / night

$3850 - $4550 / week

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from $340 / night

(12) Excellent 

29

Cruz Bay Vacation villa rental

St. John / Cruz Bay

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
Ask about our "All Inclusive Package" “Bluebitch St. John” is a quiet, tranquil villa on a private estate, ideal for a romantic, relaxing vacation. Just a 2 minute walk through our tropical garden is our secluded beach which is great for snorkeling, scuba diving & t …see more

from $400 / night

$2800 - $3150 / week

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from $400 / night

(6) Very Good 

32

Vacation villa rental

St. John / Cruz Bay

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Fanned out hillside on St. John's south shore, Pura Vida (pure life), a beautiful island home and private estate situated on 1.5 acres, is surrounded by a profusion of the native landscaping and historical Dutch ruins. This villa's hilltop location makes for lots of lov …see more

from $400 / night

$2100 - $3500 / week

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from $400 / night

(7) Very Good 

23

Vacation apartment with shared pool in Cruz Bay

St. John / Cruz Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Great view of Cruz Bay! 5 minute walk to downtown. Beautifully decorated, Seagrape is your place to stay in St. John. You will enjoy our newly remodeled kitchen and bathroom, and relax in our comfortable living room stocked with TV, air conditioning, VCR/DVD, WiFi, bo …see more

from $250 / night

$1500 - $2800 / week

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from $250 / night

22

Villa rental in Cruz Bay

St. John / Cruz Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Blue Skies Villa is located in St. John's popular upscale Great Cruz Bay area. It is on a picturesque and quiet estate road with similar rental properties. Access is extremely easy, as it is located within two miles of Cruz Bay, yet you will enjoy total privacy. You can …see more

from $680 / night

$4760 - $7000 / week

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from $680 / night

(3) Very Good 

7

Vacation cottage rental

St. John / Cruz Bay

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
Cozy clean comfortable and best of all affordable Cottage. There is view on water everywhere on the drive to and from home. The Cottage is surrounded by fruit trees and flowers. Private driveway for privacy. Screened in porch for morning coffee and evening dinners. WIFI …see more

from $135 / night

$950 / week

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from $135 / night

(1) Excellent 

14

Vacation apartment with shared pool in Cruz Bay

St. John / Cruz Bay

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Swimming pool
  • Air conditioning
Stunning sunsets and million dollar views of St. Thomas and surrounding islands! In a quiet neighborhood just around the corner from Cruz Bay, less than 5 minutes from shopping, dining and the National Park Beaches. This lower level one bedroom apartment in our home i …see more

from $225 / night

$1417 - $1418 / week

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from $225 / night

(3) Excellent 

10

Vacation home with swimming pool in Cruz Bay

St. John / Cruz Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Stunning ocean views are the first sight for the Waterklip visitor. Entering from the quite street above, through the impressive electronic gate, guests meander down a graceful stone walkway, where the first smiles bloom with the sight of the welcoming pool and patio, …see more

from $300 / night

$2100 - $2950 / week

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from $300 / night

(7) Excellent 

22

Villa rental in Cruz Bay

St. John / Cruz Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
NEW TO ST. JOHN VILLA MARKET. “THREE PALMS” is located minutes from the heart of Cruz Bay directly on the Ocean. this fantastic location provides a home base for families or groups searching for St. John adventure. Enjoy indoor/outdoor living with verandas reaching out …see more

from $858 / night

$6000 / week

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from $858 / night

(5) Excellent 

20

Vacation villa in Cruz Bay

St. John / Cruz Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Sorrento Villa Sorrento is a 3 bedroom, 3.5 bathroom property with marble and wood finishings featuring huge windows that encase a live artistic installation; that of the Caribbean’s turquoise waters against a backdrop of jagged islands. The views are brilliant by day, …see more

from $520 / night

$3640 / week

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from $520 / night

17

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
New listing on TripAdvisor, contact us for access to our 5-star reviews! We fell in love with St. John and decided to make it our destination home on retirement. After looking at many homes we kept coming back to the beautiful villas at Sirenusa where we picked what we …see more

from $300 / night

$2100 / week

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from $300 / night

(6) Very Good 

23

Vacation home rental

St. John / Cruz Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in Chocolate Hole, with a Southern view of the Caribbean Sea, POI PU is ideal for the family or couples traveling together. The secluded location surrounded by beautiful tropical flower gardens lets you enjoy a very private vacation. POI PU is located just 5 min …see more

from $300 / night

$2100 - $4025 / week

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from $300 / night

27

Vacation apartment with shared pool in Cruz Bay

St. John / Cruz Bay

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Rainbow's End condo is located adjacent to the inviting blue tiled community pool at Battery Hill Condos and is accessed down a graceful tiled stairway leading from the private complex parking area.   Rainbow's End features a unique private wrap around deck covering two …see more

from $230 / night

$1603 - $3431 / week

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from $230 / night

16

Home rental in Cruz Bay with swimming pool

St. John / Cruz Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Starvilla is conveniently located in walking distance to Cruz Bay. It is a one story home with spectacular westerly views of beautiful sunsets. This spacious villa has domed ceilings, rattan furnishings and an open floor plan. A private pool and expansive wooden deck wr …see more

from $325 / night

$2225 - $2908 / week

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from $325 / night

(12) Very Good 

21

Vacation apartment with shared pool in Cruz Bay

St. John / Cruz Bay

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Perched on the hillside overlooking Cruz Bay Harbor, The Cottage is conveniently located within walking distance to the village of Cruz Bay and an eclectic assortment of duty-free shopping, activity centers, taxi stand, and a variety of first class restaurants for casua …see more

from $195 / night

$1365 - $2429 / week

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from $195 / night

9

Home accommodation in Cruz Bay

St. John / Cruz Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Cinnamon Day Dreams is a spacious 2-level 'villa with a magnificent view' located on St. John's exclusive North Shore. Most of the living areas are on the main level. The name 'Cinnamon Day Dreams' is an accurate description of the setting - plenty of privacy, peace a …see more

from $643 / night

$4500 - $9460 / week

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from $643 / night

12

Vacation apartment with shared pool in Cruz Bay

St. John / Cruz Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Tropical Breeze Condo is a large penthouse unit located at the Battery Hill Condominiums.  This elegantly cozy 9-unit complex is conveniently located on the crest of a hill overlooking the quaint village of Cruz Bay. From this in-town location, it is but a short walk fr …see more

from $260 / night

$1820 - $3003 / week

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from $260 / night

41

Vacation apartment in Cruz Bay

St. John / Cruz Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Palmy Daze features a wonderful, open and airy feel with its vaulted beam ceilings and abundance of windows that allow the refreshing trade wind breezes to the provide natural cooling for the living spaces.  Arriving at Pastory Condominiums, guests vacationing at Palmy …see more

from $196 / night

$1372 - $2450 / week

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from $196 / night

(16) Excellent 

25

Cruz Bay Vacation villa rental

St. John / Cruz Bay

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
Desirable Chocolate Hole huge lot with panoramic ocean views and sea breezes. In the category of the ocean view villas on St John, Blue Agave Villa has location, location, location! http://youtu.be/Bfudyj3c2LE is a utube video made by a drone flying over our vil …see more

from $560 / night

$3900 - $7500 / week

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from $560 / night

(5) Very Good 

31

Cruz Bay Vacation townhouse rental

St. John / Cruz Bay

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunset Ridge Villa B is a deluxe level 2 bedroom, 2 1/2 bath townhouse villa offering approximately 1800 s.f. of combined living space. Villa B features a secure, street level entrance through lush tropical gardens opening to a private courtyard with dramatic and panora …see more

from $250 / night

$1750 - $4480 / week

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from $250 / night

(5) Excellent 

26

Cruz Bay Vacation home rental

St. John / Cruz Bay

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
"Overlooking the incredible Caribbean Sea and within a mile of Cruz Bay, St. John, Dream Seahas a secluded and unparalleled view. By day, sunset, or night the 180 degree vista of St. Thomas and the Sir Frances Drake Passage, with its rich history of pirates and treasur …see more

from $386 / night

$2700 - $6750 / week

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from $386 / night

(3) Excellent 

30

Cruz Bay Vacation townhouse rental

St. John / Cruz Bay

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunset Ridge Villa E is a deluxe level 2 bedroom, 2 1/2 bath townhouse villa offering approximately 1800 s.f. of combined living space. Villa E features a secure, street level entrance through lush tropical gardens opening to a private courtyard with dramatic and panora …see more

from $250 / night

$1750 - $4480 / week

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from $250 / night

10

Vacation home in Cruz Bay

St. John / Cruz Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Papaya II has a full kitchen, and two dining areas – dine indoors or on the veranda. The kitchen has a gas cook top, microwave/convection oven, refrigerator, microwave, toaster, blender, and coffee maker. There are plenty of clean linens for your stay. Log onto our WIFI …see more

from $225 / night

$1525 - $2215 / week

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from $225 / night

27

Vacation apartment with shared pool in Cruz Bay

St. John / Cruz Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Panacea is located on the ground floor in one of the two three story buildings at Battery Hill Condominiums.   Access to this conveniently located condo is via a gate from the adjacent private, paved parking lot for the complex.  The Battery Hill Condominiums are centra …see more

from $215 / night

$1505 - $3745 / week

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from $215 / night

(2) Excellent 

20

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Milan Villa Milan is a spacious 2-bedroom property with marble and wood finishings featuring huge windows that encase a live artistic installation; that of the Caribbean’s turquoise waters against a backdrop of jagged islands. The views are brilliant by day, shimmering …see more

from $430 / night

$3010 / week

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from $430 / night

(6) Excellent 

14

Vacation home in Cruz Bay

St. John / Cruz Bay

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Cruz Bay Cottage is one of the last of the lovely traditional West Indian cottages on St. John. It is located on a quiet little hill above Cruz Bay, within easy walking distance of the town, enjoying a birds eye view of the harbor and St. Thomas with it’s dazzling light …see more

from $300 / night

$1950 / week

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from $300 / night

(9) Very Good 

34

Vacation townhouse with shared pool in Cruz Bay

St. John / Cruz Bay

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunset Ridge Villa D is a deluxe level 2 bedroom, 2 1/2 bath townhouse villa offering approximately 1800 s.f. of combined living space. Villa D features a secure, street level entrance through lush tropical gardens opening to a private courtyard with dramatic and panora …see more

from $250 / night

$1750 - $4480 / week

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from $250 / night

21

Cruz Bay Vacation villa rental

St. John / Cruz Bay

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
Plumeria is located atop Gifft Hill, and features panoramic ocean views of up to twenty islands and cays, as well as spectacular sunsets, among the finest on St. John. Its layout provides the ultimate in Caribbean indoor/outdoor living, with large French doors in every …see more

from $400 / night

$2800 - $6201 / week

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from $400 / night

30

Villa rental in Cruz Bay with swimming pool

St. John / Cruz Bay

9 22 Min stay varies

  • 9 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
A La Mer a magnificent and ever popular estate is located on Great Cruz Bay. This Waterfront Property is a few minutes drive from Cruz Bay. The main villa is definitely the hub of it all as the large and inviting pool is just footsteps away from the pool cabana. T …see more

from $6071 / night

$42490 - $52955 / week

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from $6071 / night

19

Vacation villa rental

St. John / Cruz Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Villa Psari overlooks the natural beauty of Fish bay. Bring a set of binoculars to watch birds flying over head and into the mangroves below the villa. Bird lovers will enjoy the vantage point Psari affords. Psari is the Greek word for fish. You will see why the owners' …see more

from $286 / night

$2000 - $4500 / week

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from $286 / night

(8) Very Good 

30

Cruz Bay Vacation townhouse rental

St. John / Cruz Bay

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunset Ridge Villa F is a deluxe level 2 bedroom, 2 1/2 bath townhouse villa offering approximately 1800 s.f. of combined living space. Villa F features a secure, street level entrance through lush tropical gardens opening to a private courtyard with dramatic and panora …see more

from $250 / night

$1750 - $4480 / week

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from $250 / night

1