50 Best Cruz Bay Villas on Holiday Lettings - Vacation rentals

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657 Vacation rentals

20

Vacation home rental

St. John / Cruz Bay

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.08 mi
  • Child friendly
ST JOHN IS MAKING AN AMAZING RECOVERY AFTER THE HURRICANES! OFFERING SUMMER RATES THIS WINTER! WE APPRECIATE YOUR CONTINUED SUPPORT OF OUR BEAUTIFUL ISLAND! Thank you everyone for your kind thoughts and wishes for recovery! St. John weathered the strongest hurricane …see more

from $250 / night

$1,500 - $2,160 / week

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from $250 / night

(13) Very Good 

Certificate of Excellence

33

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. THE CONDO SUSTAINED NO DAMAGE FROM THE RECENT HURRICANES, WAP …see more

Certificate of Excellence

from $169 / night

$1,183 / week

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from $169 / night

37

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Blue Papaya Villa is a luxurious Brand New 5 BR estate home in the exclusive Virgin Grand Estates. This beautiful home offers everything the good life on St. John is all about. Enter the home through native stone walkways, and a charming trellised pergola. Lush colorful …see more

from $592 / night

$4,150 - $10,500 / week

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from $592 / 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

$2,408 - $3,255 / week

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from $344 / 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
Rates posted reflect a post-hurricane discount for a stay booked BEFORE February 28, 2018 for a stay BEFORE December 19, 2018.   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 bedro …see more

from $332 / night

$2,324 - $4,900 / week

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from $332 / night

14

Vacation villa rental

St. John / Cruz Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sea Breeze was remodeled to create what we feel is the most elegant of all the Battery Hill units. Some of the upgrades include; antiques and fine furnishings throughout, new marble floors, hand rubbed mahogany doors, marble new countertops and mahogany cabinets in the …see more

from $440 / night

$1,750 - $3,696 / week

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from $440 / 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 $295 / night

$2,065 - $4,200 / week

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from $295 / 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
Rates posted reflect a post-hurricane discount for a stay booked BEFORE February 28, 2018 for a stay BEFORE December 19, 2018.   The Cottage at Battery Hill Condos is an intimate, recently renovated queen studio cottage perched on the hillside overlooking Cruz Bay Harb …see more

from $195 / night

$1,365 - $2,429 / week

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from $195 / night

(10) Very Good 

28

Cruz Bay Vacation villa rental

St. John / Cruz Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Time Out is a relatively new fully air-conditioned villa overlooking Chocolate Hole, the Caribbean Sea and beyond to the peaks of St. Thomas. Nestled into a low green hillside, the villa enjoys lovely ocean and island views as well as Technicolor sunsets at the end of s …see more

from $384 / night

$2,690 - $5,300 / week

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from $384 / night

19

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
VILLA HIBISCUS is a luxurious, fully air conditioned 3 bedroom villa located high above sea level on beautiful St John, US Virgin Islands. Conveniently located in the upscale, gated community of Virgin Grand Estates, Villa Hibiscus is but a short drive to the eclectic v …see more

from $410 / night

$2,870 - $4,400 / week

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from $410 / night

(1) Excellent 

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

$3,500 - $5,495 / week

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from $500 / night

23

Cruz Bay Vacation villa rental

St. John / Cruz Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
Orchid Villa is a 3 bedroom, 3 bath villa was built in 1991 and in 2009 it was remodeled and completely refurnished and refurbished, (see Caribbean Villas’ Comments), and Orchid now has the look and feel of a newly built villa. Orchid is a two level design with most of …see more

from $635 / night

$2,380 - $5,334 / week

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from $635 / night

(11) Very Good 

27

Cruz Bay Vacation villa rental

St. John / Cruz Bay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Rates posted reflect a post-hurricane discount for a stay booked BEFORE February 28, 2018 for a stay BEFORE December 19, 2018. Phoenix By The Sea 'hangs' majestically from the hillside overlooking beautiful Rendezvous Bay on the southern shore of St. John.   This elega …see more

from $405 / night

$2,835 - $5,075 / week

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from $405 / night

21

Vacation villa with shared 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
Unit One (and Unit Two) are upscale 1500+ sq/ft, 2-bedroom/2-bath units, while the Penthouse on the top floor is a luxury 1-bedroom, 1-bath unit. Covered exterior stairs lead up to Unit One where you enter into the great room, which contains the living, dining and kitch …see more

from $400 / night

$2,800 - $4,410 / week

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from $400 / 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 A features a secure, street level entrance through lush tropical gardens opening to a private courtyard with dramatic and panora …see more

from $295 / night

$2,065 - $4,200 / week

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from $295 / 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

$1,855 - $3,220 / week

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from $265 / night

(4) Excellent 

30

Vacation villa with swimming pool in Cruz Bay

St. John / Cruz Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Rates posted reflect a post-hurricane discount for a stay booked BEFORE February 28, 2018 for a stay BEFORE December 19, 2018.   Sea Dream Villa is a deluxe 3 bedroom/3 bath vacation home with private pool and magnificent Ocean Views! Located on a hillside overlooking …see more

from $392 / night

$2,744 - $4,900 / week

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from $392 / night

(6) Excellent 

28

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 C is a deluxe level 2 bedroom, 2 1/2 bath townhouse villa offering approximately 1800 s.f. of combined living space. Villa A features a secure, street level entrance through lush tropical gardens opening to a private courtyard with dramatic and panora …see more

from $295 / night

$2,065 - $4,200 / week

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from $295 / night

(3) Excellent 

18

Cruz Bay Vacation apartment rental

St. John / Cruz Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome! Our luxurious studio apartment in the Sirenusa resort accommodates 2 people. It is but 1 mile from the ferry dock in a luxurious gated community that overlooks Cruz Bay and St. Thomas with gorgeous sunsets. There is a club pool for your enjoyment as well as …see more

from $150 / night

$1,050 / week

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from $150 / night

15

Cruz Bay Vacation villa rental

St. John / Cruz Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunset Vista is a very handsome 3-level design with most of the living areas on the main (2nd) floor. You park on the 2nd level and enter the great room and stare – the amazing view comes at you through a 16 foot vertical wall of glass. There are two guest bedrooms on t …see more

from $629 / night

$4,400 - $6,440 / week

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from $629 / night

(2) Excellent 

10

Vacation villa with swimming pool in Cruz Bay

St. John / Cruz Bay

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
As always 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 …see more

from $350 / night

$2,450 - $3,850 / week

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from $350 / 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 $300 / night

$2,100 - $4,500 / week

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from $300 / 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! As if of December 7, 2017 we have POWER!!! Monthly Rates Available. 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 Sui …see more

from $225 / night

$1,575 - $2,800 / week

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Responds fast!
avg. 2 hours 32 minutes

from $225 / 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

$1,820 - $3,003 / week

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from $260 / night

(6) 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 A is a deluxe level 2 bedroom, 2 1/2 bath townhouse villa offering approximately 1800 s.f. of combined living space. Villa A features a secure, street level entrance through lush tropical gardens opening to a private courtyard with dramatic and panora …see more

from $295 / night

$2,065 - $4,200 / week

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from $295 / 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

$2,100 - $2,520 / week

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Responds fast!
avg. 1 hour 55 minutes

from $300 / night

23

Cruz Bay Vacation guest house rental

St. John / Cruz Bay

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Private garden
Enjoy close proximity to Frank Bay Beach, Frank Bay Pond and town-3 minutes to the beach, 7 minutes to town! Peacocks and other wildlife, plus our unique eco-friendly amenities complete your paradise experience. Royal Palm is for those who like natural elegance. The b …see more

from $140 / night

$980 / week

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Responds fast!
avg. 3 hours 42 minutes

from $140 / night

(5) Excellent 

28

Vacation villa accommodation

St. John / Cruz Bay

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Rates posted reflect a post-hurricane discount for a stay booked BEFORE February 28, 2018 for a stay BEFORE December 19, 2018. Sweet Surrender is a luxurious, fully air-conditioned, 5 Bedroom/5.5 Bath villa located high on a hillside in the upscale, gated community of V …see more

from $750 / night

$5,250 - $9,415 / week

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from $750 / night

(1) Very Good 

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 $260 / night

$1,795 - $2,215 / week

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Responds fast!
avg. 37 minutes

from $260 / night

24

Vacation villa in Cruz Bay

St. John / Cruz Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Virgin Seabreeze consists of a large main house and a smaller guest house. You park above the villa and walk down a brick and stone stairway to the brick patio connecting the main house and the guest house. The living, dining and kitchen areas, the master bedroom, and t …see more

from $455 / night

$3,185 - $4,930 / week

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from $455 / night

30

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $1,429 / night

$10,003 - $22,001 / week

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from $1,429 / 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

$2,800 / week

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Responds fast!
avg. 1 hour 51 minutes

from $400 / 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 $857 / night

$5,999 - $11,999 / week

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Responds fast!
avg. 3 hours 1 minutes

from $857 / night

(7) Excellent 

22

Villa rental in Cruz Bay

St. John / Cruz Bay

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 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 $571 / night

$4,000 - $6,000 / week

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from $571 / night

24

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Ciellodonna is a spacious and exceedingly comfortable 2-level home with 2400 sq./ft of interior space and an abundant 3400 sq./ft of decks. You park on the upper level and enter into the large great room, which contains the living, dining and kitchen areas. Six sets of …see more

from $300 / night

$2,095 - $8,442 / week

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from $300 / 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

$5,075 / week

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from $725 / night

40

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
Like its neighboring villa, Peace and Plenty, Cinnamon Ridge is an expanded design that extends more than 150 feet from the house to the pool deck. All the living areas and bedrooms are under one roof, with the large pool and sundeck on the west (sunny) side of the vill …see more

from $450 / night

$3,150 - $10,656 / week

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from $450 / 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 A features a secure, street level entrance through lush tropical gardens opening to a private courtyard with dramatic and panora …see more

from $295 / night

$2,065 - $4,200 / week

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from $295 / night

29

Vacation villa with shared pool in Cruz Bay

St. John / Cruz Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The traditional 2 level design of La Collina is spacious and comfortable, with a 55 foot partially covered deck off the living room, a beautiful tiled sun deck and terraced gardens around the pool, 30 foot cathedral ceilings, tiled floors, over-sized arched doors, and a …see more

from $309 / night

$2,160 - $6,048 / week

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from $309 / night

23

Cruz Bay Vacation villa rental

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 and Villa Hibiscus were both designed and built by the same developer who built the Hyatt Virgin Grand of St John (now the 4 star Westin Resort). Completed in 1995, this 2-story villa incorporates many of the appealing features of the luxury hotel that is …see more

from $410 / night

$2,870 - $7,042 / week

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from $410 / night