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  • Caribbean (246)
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  • x Caribbean
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4 Bedroom Montego Bay Villa
4 Bedroom Montego Bay Villa
4 Bedroom Montego Bay Villa
4 Bedroom Montego Bay Villa
4 Bedroom Montego Bay Villa

Tradewinds Villa at Tryall Club

Montego Bay Villa
4 Bed, 4 Bath, Sleeps 8  
Per week $11,550 - $22,400
 
4 Bedroom Providenciales Villa
4 Bedroom Providenciales Villa
4 Bedroom Providenciales Villa
4 Bedroom Providenciales Villa
4 Bedroom Providenciales Villa

Tre Desideri Beach Front on Taylor Bay

Providenciales Villa
4 Bed, 4 Bath, Sleeps 14   3,260 sq. f.
Per night $929 - $1,429
 (1)
6 Bedroom St. John Apartment
6 Bedroom St. John Apartment
6 Bedroom St. John Apartment
6 Bedroom St. John Apartment
6 Bedroom St. John Apartment

Hillcrest, St. John, US Virgin Islands

St. John Apartment
6 Bed, 6 Bath, Sleeps 4   500 sq. f.
Per night from $249
 (1)
4 Bedroom Saint Martin Villa
4 Bedroom Saint Martin Villa
4 Bedroom Saint Martin Villa
4 Bedroom Saint Martin Villa
4 Bedroom Saint Martin Villa

La Savane

Saint Martin Villa
4 Bed, 4 Bath, Sleeps 8  
Per night $572 - $1,715
 
3 Bedroom Abaco Cottage
3 Bedroom Abaco Cottage
3 Bedroom Abaco Cottage
3 Bedroom Abaco Cottage
3 Bedroom Abaco Cottage

Charming & Colorful Bahamian Cottage Great Guana Cay Abaco Bahamas

Abaco Cottage
3 Bed, 2 Bath, Sleeps 6   1,200 sq. f.
Per night from $249
 
2 Bedroom Aruba (general) Villa
2 Bedroom Aruba (general) Villa
2 Bedroom Aruba (general) Villa

Modern, Spacious & Affordable Holiday Town Home

Aruba (general) Villa
2 Bed, 3 Bath, Sleeps 5   1,188 sq. f.
Per night from $249
 (1)
3 Bedroom Atlantica Beach Club Condo
3 Bedroom Atlantica Beach Club Condo
3 Bedroom Atlantica Beach Club Condo
3 Bedroom Atlantica Beach Club Condo
3 Bedroom Atlantica Beach Club Condo

Stunning View of Caribbean 3 Bedroom 2 Bath Condo in Dawn Beach

Atlantica Beach Club Condo
3 Bed, 2 Bath, Sleeps 6   1,650 sq. f.
Per night $215
 (1)
4 Bedroom Saint Martin Villa
4 Bedroom Saint Martin Villa
4 Bedroom Saint Martin Villa
4 Bedroom Saint Martin Villa
4 Bedroom Saint Martin Villa

Le Rocher

Saint Martin Villa
4 Bed, 4 Bath, Sleeps 8  
Per week $7,200 - $21,000
 
7 Bedroom Quarter of Soufriere House
7 Bedroom Quarter of Soufriere House
7 Bedroom Quarter of Soufriere House
7 Bedroom Quarter of Soufriere House
7 Bedroom Quarter of Soufriere House

Villa Coulibri, architectural statement in Unesco Heritage site.

Quarter of Soufriere House
7 Bed, 7 Bath, Sleeps 14   4,000 sq. f.
Per night $750 - $1,750
 (1)
3 Bedroom Saint Martin Villa
3 Bedroom Saint Martin Villa
3 Bedroom Saint Martin Villa
3 Bedroom Saint Martin Villa
3 Bedroom Saint Martin Villa

Arcadia

Saint Martin Villa
3 Bed, 3 Bath, Sleeps 6  
Per night $400 - $643
 
1 Bedroom US Virgin Islands Condo
1 Bedroom US Virgin Islands Condo
1 Bedroom US Virgin Islands Condo
1 Bedroom US Virgin Islands Condo
1 Bedroom US Virgin Islands Condo

Beachtacular! @ Sapphire Beach Resort in St Thomas, USVI

US Virgin Islands Condo
1 Bed, 1 Bath, Sleeps 4  
Per night $200 - $275
 (10)
7 Bedroom Parish of Saint Ann Villa
7 Bedroom Parish of Saint Ann Villa
7 Bedroom Parish of Saint Ann Villa
7 Bedroom Parish of Saint Ann Villa
7 Bedroom Parish of Saint Ann Villa

Whispering Waters

Parish of Saint Ann Villa
7 Bed, 7 Bath, Sleeps 14  
Per week $17,500 - $19,500
 
2 Bedroom Governor's Harbour House
2 Bedroom Governor's Harbour House
2 Bedroom Governor's Harbour House
2 Bedroom Governor's Harbour House
2 Bedroom Governor's Harbour House

Historic Estate with Spectacular Ocean Views, Walk to Town, Free Flights Included!

Governor's Harbour House
2 Bed, 3 Bath, Sleeps 5   2,977 sq. f.
Per night $310 - $500
 
10 Bedroom Ocho Rios Villa
10 Bedroom Ocho Rios Villa
10 Bedroom Ocho Rios Villa
10 Bedroom Ocho Rios Villa
10 Bedroom Ocho Rios Villa

Kai Kala

Ocho Rios Villa
10 Bed, 10 Bath, Sleeps 20  
Per night $1,821 - $3,500
 
2 Bedroom Rainbow Beach Club Condo
2 Bedroom Rainbow Beach Club Condo
2 Bedroom Rainbow Beach Club Condo
2 Bedroom Rainbow Beach Club Condo
2 Bedroom Rainbow Beach Club Condo

St.Maarten Oceanfront Penthouse Condo With Rooftop Terrace

Rainbow Beach Club Condo
2 Bed, 2 Bath, Sleeps 6   1,200 sq. f.
Per night $250 - $285
 (1)
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Connecting Rentals Worldwide
Price per night: $ - $
Caribbean
  •   Anguilla
  •   Antigua & Barbuda
  •   Aruba
  •   Bahamas
  •   Barbados
  •   Cayman Islands
  •   Cuba
  •   Curacao
  •   Dominican Republic
  •   Honduras
  •   Jamaica
  •   Puerto Rico
  •   Saint Lucia
  •   Saint Martin
  •   Turks & Caicos Islands
  •   Virgin Islands
Property Types
  •   Apartments
  •   Condos
  •   Cottages
  •   Houses
  •   Villas
  •   Yachts
Property Features
  •   Air Conditioning
  •   Fireplace
  •   Hot Tub
  •   Outdoor Grill
  •   Pool
Preferences
  •   Child Friendly
  •   Elderly Accessible
  •   Pet Friendly
  •   Seasonal
  •   Wheelchair Accessible
Themes
  •   Downtown
  •   Family Reunion
  •   Golfing
  •   Lake
  •   Mountain
  •   Ocean
  •   River
  •   Ski in Ski out
  •   Skiing
  •   Slopeside
  •   Waterfront
Connecting Rentals Worldwide