50 Best Cruz Bay Villas on Holiday Lettings - Vacation rentals

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154 Vacation rentals

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 - $3300 / week

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from $200 / night

(4) 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

(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

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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Responds fast!
avg. 3 hours 54 minutes

from $715 / night

(17) 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 $330 / night

$3850 - $4550 / week

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from $330 / night

(7) Excellent 

25

Vacation villa with swimming pool in Cruz Bay

St. John / Cruz Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Pisa Villa Pisa is a spacious 3 bedroom, 3.5 bathroom (with private pool) 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 ar …see more

from $725 / night

$5075 / week

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from $725 / night

29

Vacation home with swimming pool in Cruz Bay

St. John / Cruz Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sea Dream is a 3 bedroom villa also available as a 2 bedroom rental for 2-4 guests.   This listing reflects the rates for the use of 2 bedrooms and does not include applicable taxes and fees.  The 3rd bedroom will not be occupied during your stay. Sea Dream Villa offers …see more

from $333 / night

$2324 - $4900 / week

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from $333 / 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 2 Bed/2 Bath penthouse unit located in the Battery Hill Condominiums complex.  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 i …see more

from $260 / night

$1820 - $3003 / week

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from $260 / night

(6) Excellent 

14

Vacation home in Cruz Bay

St. John / Cruz Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $225 / night

$1575 - $1950 / week

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from $225 / night

(2) Excellent 

34

Villa rental in Cruz Bay with swimming pool

St. John / Cruz Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Ilios - from the Ancient Greek term for 'sun' or 'sunlight', was constructed as a modern interpretation of an old Greek villa by combining the beauty of classic Mediterranean architecture with the comforts and conveniences of a present day tropical vacation home .  Stay …see more

from $395 / night

$2766 - $5376 / week

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from $395 / 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 $170 / night

$1184 / week

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Responds fast!
avg. 3 hours 26 minutes

from $170 / 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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Responds fast!
avg. 1 hour 48 minutes

from $400 / night

(10) 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 0.7 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. The t …see more

from $280 / night

$2000 - $4550 / week

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from $280 / 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 $575 / night

$4025 / week

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from $575 / 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 $110 / night

$771 - $950 / week

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Responds fast!
avg. 1 hour 50 minutes

from $110 / night

(9) Excellent 

45

Cruz Bay Vacation villa accommodation

St. John / Cruz Bay

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Serendipity is a beautifully appointed 5 bedroom/5 bath villa located high above Chocolate Hole Bay featuring a gorgeous full length pool and sun deck with built in swimming pool.  The pool deck also features numerous seating and lounging areas, including the uniq …see more

from $785 / night

$5495 - $8680 / week

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from $785 / 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, is a deluxe 2 bedroom condo with pool located in the upscale Battery Hill Condominium Complex in Cruz Bay.  Battery Hill Condos are considered to be one of St John's more desirable addresses for in-town tropical vacation living. Overlooking Cruz Bay Harbo …see more

from $344 / night

$2408 - $3255 / week

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from $344 / 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

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
Blue Coral is a very popular 3 bedroom, 3 bath with central air conditioning vacation rental condo offering first class accommodations and convenient location! From its penthouse location in the small quiet, 6 unit Palm Terrace Villas complex, Blue Coral is just a short …see more

from $426 / night

$2975 - $4375 / week

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from $426 / night

45

Cruz Bay Vacation condo rental

St. John / Cruz Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
As part of the renown Grande Bay Resort, this spacious 3 bdrm-2 bath condo can accommodate up to 8 guests with 2 king beds, 2 twin beds and a brand new queen pull-out sofa sleeper. The unit is fully wi-fi capable; all rooms have flatscreen TV's with cable hookup. The …see more

from $450 / night

$3150 / week

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from $450 / night

19

Vacation villa rental

St. John / Cruz Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Imola Villa Imola is a spacious 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 da …see more

from $575 / night

$4025 / week

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from $575 / night

23

Cruz Bay Vacation home rental

St. John / Cruz Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Guests arriving at Cocoa Reef enter the villa by descending a short native stone lined stairway from the private parking area.  This will lead to the upper level covered breezeway between the great room and the upper bedrooms.  The breezeway features an open but covered …see more

from $300 / night

$2100 - $5390 / week

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from $300 / 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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Responds fast!
avg. 2 hours 7 minutes

from $400 / night

31

Villa rental in Cruz Bay with swimming pool

St. John / Cruz Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set amongst lush, tropical landscaping, Villa Hibiscus is a luxurious, fully air conditioned 3 bedroom, 3.5 bath villa located high above sea level in the upscale, gated community of Virgin Grand Estates.  The large and comfortable great room features Caribbean decor, v …see more

from $500 / night

$3500 - $5495 / week

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from $500 / 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

47

Villa accommodation in Cruz Bay with swimming pool

St. John / Cruz Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Del Sol is a luxury three bedroom, three and a half bath villa set high above sea level in the upscale, gated community of Virgin Grand Estates. Once inside the gates at Virgin Grand Estates it is a short drive to the private parking area adjacent to the entrance …see more

from $500 / night

$3500 - $5096 / week

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from $500 / 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
The Cottage at Battery Hill Condos is an intimate, recently renovated queen studio cottage perched on the hillside overlooking Cruz Bay Harbor. Perched on the hillside overlooking Cruz Bay Harbor, The Cottage is conveniently located within walking distance to the villag …see more

from $195 / night

$1365 - $2429 / week

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from $195 / night

(1) Excellent 

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

(2) Excellent 

23

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Siena Villa Siena is a spacious 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 da …see more

from $575 / night

$4025 / week

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from $575 / 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) Very Good 

36

Vacation cottage rental

St. John / Cruz Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
The Hawks Nest cottage is a finely crafted vacation home for two in an exclusive and very private location within the borders of the U.S. Virgin Islands National Park on the North Shore of St. John. This lovely cottage has recently been renovated, including upgrades to …see more

from $325 / night

$2275 - $3465 / week

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from $325 / 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

(2) Excellent 

20

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Modena Villa Modena is a 4 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, shimm …see more

from $575 / night

$4025 / week

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from $575 / night

30

Vacation villa in Cruz Bay

St. John / Cruz Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Built in 2008, the VI Friendship Villa serves as the second home to longtime visitors to the United States Virgin Islands who finally decided on creating their own little "slice of heaven" in paradise. Designed from a unique and nautical perspective, VI Friendship Villa …see more

from $1442 / night

$10100 - $23100 / week

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from $1442 / night

26

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

9 22 Min stay varies

  • 9 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Ask about children
Situated on over one acre of waterfront land behind an electronic gate landscaped with tropical flowers and graceful royal, foxtail and coconut palm trees, spectacular À La Mer's large-scale design and execution is an artful combination of both colonial West Indies and …see more

from $5280 / night

$36960 - $52955 / week

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from $5280 / night

(1) Excellent 

21

Vacation villa 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
Clinging to the hillside above Cruz Bay, Perelandra's breathtaking views sweep from the deserted cays nestled in the Windward Passage to the sailboats skimming through Pillsbury Sound. Upstairs or down, inside or out, the views, privacy, comfort and romantic ambiance of …see more

from $357 / night

$2499 - $4753 / week

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from $357 / night

(5) Excellent 

34

Vacation villa in Cruz Bay

St. John / Cruz Bay

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Pet friendly
Experience the beauty and untouched nature of St. John (A.K.A. “The Love City”) at The Love Palace, a gorgeous 3 bedroom, 2 bathroom villa located minutes from the buzzing downtown of Cruz Bay. 22 windows and 12 french doors gives this home ample natural light and tons …see more

from $300 / night

$2200 - $3701 / week

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from $300 / night

(2) Excellent 

10

Vacation villa in Cruz Bay

St. John / Cruz Bay

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
Villa Divertimento is a two bedroom, two bath villa with a beautiful thirty foot pool on the south shore of St. John. The villa comfortably accommodates up to two couples with (or without) their children. There are two large bedrooms with en suite baths and stone sho …see more

from $350 / night

$2450 - $3850 / week

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from $350 / 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 a deluxe 2 bedroom, 2 full bath condo located in the upscale Battery Hill Condominium complex. From this conveniently located accommodation, it is just a short walk to the many dining and shopping options found in Cruz Bay and to Frank Bay which features a ni …see more

from $265 / night

$1856 - $3220 / week

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from $265 / night

(1) Excellent 

25

Vacation villa with swimming pool in Cruz Bay

St. John / Cruz Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sundancer Villa is a beautiful Caribbean style three bedroom, two bath vacation villa with pool and hot tub located in the Fish Bay community on St. John in the beautiful U.S. Virgin Islands. Affording breathtaking views of Fish Bay and the Caribbean Sea beyond, Sundanc …see more

from $374 / night

$2618 - $3619 / week

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from $374 / night

1