50 Best Cruz Bay Villas on Holiday Lettings - Vacation rentals

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602 Vacation rentals

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 $250 / night

$1,750 - $3,696 / week

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from $250 / night

33

Vacation home 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
Silver Palm is a magnificent, luxury condo in the heart of Cruz Bay that recently underwent a top to bottom renovation. With a complete assortment of upscale amenities,Silver Palm is one of the few condos in Cruz Bay with 4 bedrooms that can easily accommodate 4 couples …see more

from $425 / night

$2,975 - $4,900 / week

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from $425 / 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

19

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
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 $495 / night

$3,465 - $5,280 / week

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avg. 1 hour 47 minutes

from $495 / 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

$1,750 - $2,200 / 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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Responds fast!
avg. 3 hours 31 minutes

from $169 / 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. 2 hours 46 minutes

from $400 / night

(1) Excellent 

55

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
Low Season rates in effect for stays prior to December 19, 2018. Belle Mer Villa is a luxury vacation rental villa located beach front on Klein Bay along St. John's south shore. Direct access to the beach and Klein Bay is via a gated, private pathway from the pool deck …see more

from $550 / night

$3,850 - $6,860 / week

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from $550 / 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 $400 / night

$4,750 - $5,450 / week

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from $400 / night

(1) Excellent 

24

Cruz Bay Vacation cottage rental

St. John / Cruz Bay

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
This is the way the Caribbean used to be, old world Caribbean when ships carried sugar cane from the islands plantations to Europe. When pirates sailed the Caribbean in search of treasures and riches!No high heels here! Your private oasis awaits, this was created for ro …see more

from $350 / night

$2,395 / week

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Responds fast!
avg. 3 hours 39 minutes

from $350 / night

35

Vacation cottage 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
After 16 months of construction Gull Cottage was completely rebuilt and reborn in 1995. The new Gull resembles a picturesque chateau of the French countryside that has been blended with the best design features of an elegant island home. You enter into the living room, …see more

from $460 / night

$3,220 - $6,372 / week

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from $460 / 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

12

Cruz Bay Vacation villa rental

St. John / Cruz Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Ocean Pearl is a 2 level, 2-bedroom villa where both air conditioned bedrooms, a 20 X 12 foot pool and a 700 square foot deck are on the lower level, while the living /dining/kitchen areas, a half bath, and a wrap-around deck are on the upper level. You park on the uppe …see more

from $230 / night

$1,610 - $3,132 / week

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from $230 / 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) 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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Responds fast!
avg. 40 minutes

from $135 / 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, shim …see more

from $725 / night

$5,075 / week

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from $725 / night

(16) Excellent 

22

Vacation villa in Cruz Bay

St. John / Cruz Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This is the closest oceanfront beach house to Cruz Bay town - a very unique property. Imagine being able to take a dip in the ocean anytime you like, only steps away from your own private beach house! Seaside Vista was totally restored after the hurricanes and includes …see more

from $275 / night

$1,925 - $3,465 / week

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from $275 / 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 59 minutes

from $857 / 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 $360 / night

$2,500 - $4,850 / week

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from $360 / 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

$2,800 - $7,425 / week

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from $400 / night

(2) Excellent 

16

Home rental in Cruz Bay with swimming pool

St. John / Cruz Bay

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 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 $362 / night

$2,488 - $3,118 / week

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Responds fast!
avg. 37 minutes

from $362 / 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
Low Season rates in effect for stays prior to December 19, 2018   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 Co …see more

from $195 / night

$1,365 - $2,429 / week

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from $195 / 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 $1,857 / night

$12,999 - $22,001 / week

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avg. 1 hour 47 minutes

from $1,857 / night

36

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
  • Child friendly
  • Air conditioning
The buzz throughout St. John and in the world of luxury villas is all about the impressive scale and the barefoot elegance of A La Mer! Waterfront on Great Cruz Bay, this magnificent new estate holds court within an oasis of stately palm trees, boasting probably what is …see more

from $6,070 / night

$42,490 - $52,955 / week

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avg. 1 hour 47 minutes

from $6,070 / night

15

Vacation condo with shared pool in Cruz Bay

St. John / Cruz Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
Echo is a one-bedroom condo unit at Serendip Vacation Condos, a small 10-unit complex. The unit is spacious with air conditioning in the living room and bedroom. It has a king size bed in the bedroom and a new queen sofa sleeper in the living room. The flute-playing Ko …see more

from $165 / night

$1,155 / week

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Responds fast!
avg. 1 hour 31 minutes

from $165 / night

(1) Very Good 

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
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 $200 / night

$1,350 - $3,000 / week

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from $200 / night

(1) Good 

21

Condo rental in Cruz Bay with shared pool

St. John / Cruz Bay

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
This is a private condo in a 4 unit building with a pool and a private partially covered porch. It sits high on a hill above the city of Cruz Bay (with all the night life, restaurants, and shopping), however is still quiet and secluded. The Best Beaches in the world are …see more

from $145 / night

$1,015 / week

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Responds fast!
avg. 1 hour 17 minutes

from $145 / 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

$2,100 - $2,450 / week

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from $300 / 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

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

$2,345 - $6,544 / week

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from $455 / night

35

Home rental in Cruz Bay with swimming pool

St. John / Cruz Bay

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Low Season rates in effect for stays prior to December 19, 2018 Belle Mer is a 3 bedroom villa also available as a 2 bedroom rental for 1-4 guests.   This listing reflects the rate for the use of 2 bedrooms and does not include applicable taxes and fees.  The third be …see more

from $470 / night

$3,290 - $6,860 / week

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from $470 / night

24

Cruz Bay Vacation apartment rental

St. John / Cruz Bay

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
CRUZ VIEWS #UNIT 4 – Destiny is a 1 bedroom plus loft, 1 bath corner unit located above the pool. With its 250 sq/ft wraparound deck, this is one of the most private units at Cruz Views, and it also has one of the best views. Both the main bedroom and loft bedroom (ship …see more

from $165 / night

$1,155 / week

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from $165 / 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

(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

32

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
Dream Come True is a charming, two-level home was completed in the fall of 2004. Dream Come True incorporates many classic Caribbean design elements such as solid, concrete construction, native stone walls, Doric columns, tiled exterior decks, tiled interior floors and …see more

from $400 / night

$2,800 - $6,972 / week

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from $400 / night

(39) Excellent 

26

Vacation home in Cruz Bay

St. John / Cruz Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.02 mi
  • Swimming pool
Little Palm Guest Suite, located in a quaint island stone cottage, is the perfect romantic getaway. I'm proud that this property has received Trip Advisor's "Excellence" Badge and "Top Vacation Rental" award. You may have seen Little Palm Guest Suite on HGTV as they f …see more

from $250 / night

$1,750 - $3,465 / week

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from $250 / night

24

Villa rental in Cruz Bay

St. John / Cruz Bay

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Ask about children
  • Air conditioning
Rosebay is a cozy and romantic 1 bedroom plus a loft, 1 bath, air conditioned home that sits in the midst of a colorful, well maintained tropical garden. You park below the house and a stairway leads up to an entrance into the great room. All the rooms except the loft b …see more

from $200 / night

$1,400 - $2,345 / week

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from $200 / night

16

Vacation condo with shared pool in Cruz Bay

St. John / Cruz Bay

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
Very charming and elegantly decorated, Alpha will enhance your sense of serenity while on island. Alpha is a one-bedroom unit at Serendip vacation condos, a small 10-unit complex. Ground entry level with just one step down enables ease in loading for families with chi …see more

from $165 / night

$1,155 / week

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Responds fast!
avg. 1 hour 31 minutes

from $165 / 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 $340 / night

$2,380 - $5,334 / week

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from $340 / 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