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Caribbean vacation rentals

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Top-rated vacation rentals in Caribbean

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SUPERHOST
  1. Entire home
  2. Sosua
Casa Cascada - Check out my other listing!

Ultimate 3 bed, 4 bath Vacation Luxury Villa. This house has all the amenities and built for entertaining with TV in every room. Pool Table, Privacy, 24hr security with a beautiful infinity pool & plunge pool with views. If you want an amazing experience this house has it! NO hidden fees, NO cleaning fees, Only 3 minutes to beautiful Sosua Beach, international restaurants and bars, 5 minutes to POP airport and 15 mins to Playa Dorado golf course. This is the best location on the north coast!

G$58,299 per night
SUPERHOST
  1. Entire home
  2. Grand Cayman
Lone Palm: Oceanfront Pool, 2 Free Kayaks, & Wide Beachfront

==> Reopening Update - as of 02/22/2022 <== Traveling to Grand Cayman just got easier! As of February 18, the Cayman Islands have dropped all on-island testing for incoming travelers. Direct flights have also been expanded to include American departing from Miami, and United Airlines departing from Chicago, Houston, Newark, and Washington, DC (IAD). Additional flights from Atlanta, Charlotte, and Baltimore will be added in March. Current travel requirements include: -- Pre-register travel and vaccination status with Travel Cayman. A certificate of travel will be required for all members of your group for entry. -- Unvaccinated children ages 11 and younger will assume the vaccination status of their traveling adult/guardian. -- All travelers, ages 5 and above, must provide proof of a negative rapid test taken no earlier than the day before arrival. Your home country may require pre-departure testing for your return flight. Be sure to know your country’s testing requirements in advance. The quarantine period for unvaccinated travelers has been reduced from 10 to 7 days. Additional updates will be shared across all our listings as official guidance is made public. =================== ***Property Overview*** Welcome to Lone Palm! Nestled in Gun Bay along the East End, Lone Palm is a 3 bedroom, 3 bathroom award-winning home designed by renowned architect John Doak. An open concept living area with vaulted ceilings opens up to a full-width beachfront veranda with a private pool, sundeck, and a white sandy beach with great snorkeling. Lone Palm sleeps 8 guests across two master suites on the main floor, plus a bedroom and loft with a daybed on the second floor. The oceanfront master suite with a king-sized bed and en-suite bath include sliding glass doors onto the covered veranda, plus a flat-screen TV, and desk. The other master bedroom comes furnished with a king-sized bed, attached bathroom, and has views of the ocean and pool deck. The upstairs bedroom comes with a queen-sized bed and private bath. The loft area includes a sitting area with a daybed and trundle underneath for additional guests. Location and convenience are key factors with guests who choose to stay at Lone Palm. The home is within walking distance to Ocean Frontiers Dive Center, Big Tree BBQ, Vivine's Kitchen, and a small shop at Compass Point. Lone Palm is also often used as an overflow villa for larger families renting the Cayman Castle next door. Renting those two properties puts 950 feet of private shoreline between the two homes with 3 pools, plenty of room to entertain while still maintaining privacy. ***Lone Palm's Notable Features*** -- The oceanfront living and dining area are flooded with natural light, ocean views, and access to the beachfront veranda. -- The living area has tons of comfortable lounge seating, a flat-screen TV, and a dining table for 6. -- High-end modern kitchen with granite countertops and stainless appliances. -- Cookware, dishware, cutlery, and a coffeemaker are all provided. -- Two kayaks for guest use. -- Tukka restaurant is only a mile north and two large resorts with water sports, restaurants, grocery stores, and bars are only a mile north of that! -- 300 feet of white sand beach to the north of the villa is also available for guest use (Castle kayaks and beach chairs are private unless renting the Castle as well). -- The beach and home are very private--it's rare to see anyone during your stay. -- Perfect for honeymooners or couples looking to get away from it all! Bedroom & Bathroom Layout (Sleeps 8 guests total) -- Master Suite: ocean views, king bed, sliding glass doors onto the covered veranda, flat-screen TV, desk, ensuite bath with a walk-in shower. -- King Suite: ocean views, king bed, ensuite bath with a tub/shower combination. -- Queen Suite: upper-level, queen bed, private bath. -- The loft area includes a sitting area with a daybed and a trundle underneath for additional guests. *Notes: 1) A Cleaning Fee may be required due to enhanced cleaning, sanitation, and inspection protocols. 2) Silver Thatch kayaks are available for discounted rental. Signed waiver required. ================================= ***Villa Cleaning & Sanitation*** -- We're committed to the health and safety of all our guests and have adopted enhanced cleaning safeguards to suppress the spread of COVID-19. All villas are cleaned and sanitized prior to each guest's arrival using health agency-approved cleaners and disinfectants. We also ask our owners to provide a starter supply of extra cleaning products. -- Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival on-island. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service includes your Silver Thatch Membership. -- Owner requires a $500 refundable cleaning and damages deposit. -- We accept VISA, MC, Discover and Bank Wire for payments. ***Booking Rules*** -- 5-night minimum stay required. -- 6 nights minimum and full occupancy required over Thanksgiving week. -- 7-night minimum stay and full occupancy rate required over Christmas and New Year's week. -- Christmas & New Year's dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 or older to book and must occupy the property during the entire stay. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Queen owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to weather. The next-door beach is also always available for your use. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around mother nature. ***Silver Thatch Guest Services*** The 10% Guest Service Fee includes your Silver Thatch Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Silver Thatch Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Silver Thatch Guest Discount Card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Complimentary pack-n-plays, booster seats, & baby gates -- Referral to preferred vendors, guest services desk assistance -- Complimentary early check-in, if no check out on the same day -- $500 of Accidental Villa Damage Protection -- Additional kayaks available for discounted rental* *Signed waiver required.

G$164,075 per night
SUPERHOST
  1. Entire cottage
  2. Grand Cayman
Kai Tana: Cozy Cottage on Private Beach w/Pristine Snorkeling Near Rum Point

==> Reopening Update - as of 02/22/2022 <== Traveling to Grand Cayman just got easier! As of February 18, the Cayman Islands have dropped all on-island testing for incoming travelers. Direct flights have also been expanded to include American departing from Miami, and United Airlines departing from Chicago, Houston, Newark, and Washington, DC (IAD). Additional flights from Atlanta, Charlotte, and Baltimore will be added in March. Current travel requirements include: -- Pre-register travel and vaccination status with Travel Cayman. A certificate of travel will be required for all members of your group for entry. -- Unvaccinated children ages 11 and younger will assume the vaccination status of their traveling adult/guardian. -- All travelers, ages 5 and above, must provide proof of a negative rapid test taken no earlier than the day before arrival. Your home country may require pre-departure testing for your return flight. Be sure to know your country’s testing requirements in advance. The quarantine period for unvaccinated travelers has been reduced from 10 to 7 days. Additional updates will be shared across all our listings as official guidance is made public. =================== ***Property Overview*** Welcome to Kai Tana, a perfect 2-bedroom beachfront cottage! New homeowners have taken the best features of this beautiful oceanfront cottage and upgraded them for your comfort. Surrounded by mature palms and casuarina trees on a half-acre-sized lot, Kai Tana offers peaceful relaxation on a wide sandy beach with sophisticated accommodations for couples, honeymooners, and small families. The beach is very sandy and reef-protected making for excellent snorkeling just steps off the house. Although barefoot water entry is tempting, water shoes are recommended! Sunset walks along the expansive beach in either direction are a must. Inside, Kai Tana features an oceanfront living room with windows on three sides flooding the home with natural light and panoramic ocean views. The living room is open and airy allowing guests to "become one with the ocean" while providing all comforts and amenities. The oceanfront patio provides comfortable lounges as well as al fresco dining. A palm-shaded hammock sits off the patio and is the perfect spot for daydreamers. Kai Tana's Notable Features -- Full kitchen with granite countertops and modern appliances -- Oceanfront patio with lounges and palm-shaded hammock -- Wide sandy beach with protected reef snorkeling in your backyard! -- Close proximity to Rum Point Beach and the Kaibo -- Home security system with central monitoring hub and motion sensors. -- Motion-activated LED floodlights across the property and beach. -- Hurricane-proof glass on windows and sliding glass doors. -- Front entry secured with deadbolt and sliding locks. -- Sliding glass doors secured with barrel locks and security bars on tracks. Bedroom & Bathroom Layout (Sleeps 4 guests total) -- Master Suite: oceanfront views, king bed, patio access, TV, ensuite bath with a walk-in shower. -- Guest Suite: 2 twin beds (can be converted to a king bed upon request), ensuite bath with a combination tub/shower. Kai Tana is inspected and licensed by the Cayman Islands Department of Tourism to sleep 4 adults max. We look forward to welcoming you to our little slice of paradise! *Notes: 1) A Cleaning Fee may be required due to enhanced cleaning, sanitation, and inspection protocols. 2) Silver Thatch tandem kayaks available for discounted rental. Signed waiver required. ========================== ***Villa Cleaning & Sanitation*** -- We're committed to the health and safety of all our guests and have adopted enhanced cleaning safeguards to suppress the spread of COVID-19. All villas are cleaned and sanitized prior to each guest's arrival using health agency-approved cleaners and disinfectants. We also ask our owners to provide a starter supply of extra cleaning products. -- Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival on-island. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service includes your Silver Thatch Membership. -- Owner requires a refundable cleaning and damages deposit of $500. -- We accept VISA, MC, Discover and Bank Wire for payments. ***Booking Rules*** -- 5 nights minimum stay required. -- 5 nights minimum and full occupancy required over Thanksgiving. -- 7 nights minimum and full occupancy required over Christmas and New Year's week. -- Christmas & New Year's dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Queen owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to weather. The next-door beach is also always available for your use. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around mother nature. ***Silver Thatch Guest Services*** The 10% Guest Service Fee includes your Silver Thatch Membership. Member Benefits -- Centralized on-island guest services & welcome center -- Unlimited Use of Silver Thatch Fitness Center (18+ yrs.) -- Business Center Access: computers, printer & FedEx/DHL supplies -- Proprietary Silver Thatch Guest discount card -- 10% advance booking discount for private charter -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors and reservation assistance -- Complimentary snorkel gear, pack-n-plays, booster seats, and baby gates for check out At-Villa Benefits -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Coordinate private chefs, cooks, babysitting & family photographer -- $500 of Villa Accidental Damage Protection -- Kayaks available for discounted rental* *Signed waiver required

G$92,501 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Caribbean beach vacation rentals

SUPERHOST
  1. Entire cottage
  2. Eleuthera Island Shores
SHOREBREAK ECO COTTAGE
G$82,665 per night
SUPERHOST
  1. Entire rental unit
  2. Montego Bay
Oceanfront Apt w/ Beach Access, Pool, & Gym (2F)
G$40,809 per night
PLUS
  1. Hut
  2. Bavaro
Rekindle a Romance in a Retro Thatched Hut on the Beach
G$52,111 per night
SUPERHOST
  1. Entire cabin
  2. Bluefields
Cozy Oceanview Cabin
G$19,134 per night
  1. Entire rental unit
  2. Cartagena
26th Floor Spectacular 1 Bedroom Apt in Bocagrande
G$15,696 per night
  1. Entire home
  2. Aguadilla Pueblo
Ta-Vera Oasis
G$34,203 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Montego Bay
Calypso Shores
G$198,815 per night
SUPERHOST
  1. Entire villa
  2. Playa Sardinas I
Melones Reserve Villa w/ Stunning Ocean View
G$188,351 per night
SUPERHOST
  1. Entire cottage
  2. Runaway Bay
Bahia - Charming beach cottage, loft/wood shutters
G$56,505 per night
SUPERHOST
  1. Entire rental unit
  2. Simpson Bay
Lilly's Beach
G$35,877 per night
PLUS
  1. Entire rental unit
  2. Rincón
Rincón Beachfront Retreat. King Master with Private Balcony
G$44,039 per night
SUPERHOST
  1. Entire rental unit
  2. San Juan
Stunning Ocean View Studio : Steps to the beach
G$22,422 per night

Caribbean house rentals

SUPERHOST
  1. Entire home
  2. Key West
Blu on White - Work or Home School from Paradise!
G$90,438 per night
  1. Entire home
  2. North Side
Ocean's Edge: Beachfront Home with Rooftop Views
G$117,196 per night
SUPERHOST
  1. Entire home
  2. Fort Lauderdale
★Near Downtown & Beach- Luxury House /Heated spa★
G$101,530 per night
  1. Entire home
  2. Marathon
Gulf-Front Retreat with Private Heated Pool, Hot Tub, Boat Ramp & New Dock
G$179,352 per night
  1. Entire home
  2. Placida
Camp GoodNow: Beachfront on a tropical island!
G$99,408 per night
LUXE
  1. Entire home
  2. Harbour Island
Sea Siren
G$1,151,036 per night
  1. Entire home
  2. Captiva
Manatee Haven - Upscale Beach View Home with Screened-in Pool, Spa and Elevator!
G$125,568 per night
SUPERHOST
  1. Entire home
  2. Miami
ULTRA LUXURIOUS VILLA 4/3 LARGE POOL PFCT GETAWAY
G$131,547 per night
SUPERHOST
  1. Entire home
  2. Tower Isle
Tranquil Times Villa Jamaica
G$97,913 per night
SUPERHOST
  1. Entire home
  2. Guayama
Completely private, for couples.
G$22,303 per night
  1. Entire home
  2. Cape Coral
Completely Remodeled 3 Bedroom Home With A Pool
G$31,392 per night
SUPERHOST
  1. Entire home
  2. Cartagena
Super Luxury 7 Bedroom House in the Old City
G$156,198 per night

Caribbean luxury vacation rentals

LUXE
  1. Entire villa
  2. The Bight
Villa Islander · Tropical Brutalist architecture near the beach
G$596,446 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Cabrera
Casa Kimball
G$717,529 per night
LUXE
  1. Entire villa
  2. Montego Freeport
Afimi · Fully-staffed beach house on quiet lagoon
G$493,481 per night
LUXE
  1. Entire villa
  2. Punta Cana
Villa Rosana · Minimalist resort villa near golf and the beach
G$373,712 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Chalk Sounds
Alinna Villa · Tropical modern villa near Taylor Bay Beach
G$360,858 per night
LUXE
  1. Entire villa
  2. Leeward Settlement
Sugar Apple
G$272,063 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Grace Bay
Beach Kandi · Neomodernist villa on Grace Bay Beach
G$355,176 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Providenciales
Pearl West · Contemporary architecture on Long Bay
G$1,611,451 per night
LUXE
  1. Entire villa
  2. Ocean Drive
Balinese · Modern Ocean Drive villa above the sea
G$242,136 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Les Terres Basses
Bamboo
G$149,425 per night
LUXE
  1. Entire villa
  2. Lockrum
Champagne Shores · Contemporary oceanfront villa
G$355,775 per night
LUXE
  1. Entire villa
  2. Montego Bay
Seaside Cottage
G$747,546 per night

Your guide to Caribbean

All About the Caribbean

The Caribbean is made up of 26 island countries surrounded by bejeweled blue and green waters and is known around the world as a holiday paradise. People flock here, especially in the winter, for warm sands, golden sunshine, and that sense of island time abandon — plus, the fruity drinks under towering palm trees. The Dominican Republic is the most visited of all the islands due to its vibrant city and cultural life and postcard-perfect beaches. West of that is Cuba, famous for its Old World architecture, rich jazz and music scenes, and several UNESCO World Heritage Sites. Closer to South America is little St. Lucia, known for its rainforests, colorful coral reefs (perfect for diving and snorkeling), and, of course, pristine beaches surrounded by the island’s volcanic peaks.

The countries in the Caribbean are extremely diverse, not only in their histories, cultures, and languages, but their landscapes and topographies. For example, vibrant Jamaica could not be more different from super-chill Aruba and swanky St. Barts. So whether you’re seeking an island that’s large or small, glitzy or low-key, in the Caribbean there is a sanctuary for everyone.


How do I get around Caribbean?

Most of the capital cities in the Caribbean have airports that receive direct flights from the United States, while islands further afield and smaller cities are serviced through connecting flights from Florida. For those wanting to island hop, regional Caribbean airlines will easily take you where you want to go – but if the thought of traveling by prop plane makes you uncomfortable, consider creating your itinerary via ferry. Public boats aren’t always frequent and plentiful, so it may take some planning.

If you’re set on exploring many islands, a combination of flights and ferries is your best bet. Hiring a private boat or yacht to take you between ports is also an option. Taxis are relatively easy to find on the islands. Local buses can be a good alternative and a great way to experience local life, but depending on the island, schedules and information can be ample or limited, so do some research before deciding on your travel routes.


When is the best time to stay in a vacation rental in Caribbean?

Thanks to trade winds, the weather in the Caribbean is sunny and pleasant all year round. The only caveat is that tropical storms and hurricanes occur to varying degrees of intensity here, and their likelihood increases from about July to November. But it’s the dry season from December through March that makes the region so popular. Villas to rent in the Caribbean are in demand during the winter, as many feel the urge to escape the colder weather up north and take in the sun, fun, and the many festivals — like Trinidad’s Carnival, the biggest of the Caribbean’s carnivals, and the Bahamas’ Junkanoo, a cultural street festival and celebration dating back centuries that takes place between Boxing and New Year’s Day. There are also plenty of Caribbean rentals in May and June, if you don’t mind the chance of a little rain.


What are the top things to do in Caribbean?

Santo Domingo

Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited colonial settlement in the Western Hemisphere and was founded in 1496. The historic city center, Zona Colonial, is a UNESCO World Heritage Site, with cobblestone streets, colorful houses, and colonial-style architecture and structures like the 16th-century Basilica Cathedral of Santa María la Menor, the oldest surviving cathedral in the Americas.

Curaçao

Sitting off the coast of Venezuela is the Dutch island of Curaçao, lesser known than its neighbors, but with just as much to offer — including its lack of hurricane seasons. Willemstad, the capital, is one of the few UNESCO World Heritage cities in the Caribbean, and it’s pulsing with nightlife and festivals like Carnival and King’s Day. The diving here is top-notch, there are dozens of stunning beaches to choose from, and the lodging ranges from hostels to five-star resorts — so there’s something here for everyone.

Reggae in Jamaica

Jamaica is the birthplace of reggae. The music took off in the late 1960s, and by the 1970s, with the superstardom of Bob Marley and the Wailers, it became known throughout the world. If you’re in Kingston, check out the clubs, still playing the dub style that made the genre so popular. The best of the best musicians have been known to play at the annual reggae festival held in June.