Villas and Vacation Homes in Caribbean

1782394 Villas and Vacation Homes in Caribbean

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Caribbean
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Best villa offers in Caribbean

Luxury villas in the Caribbean

Expansive cliffside estates, secluded island compounds, and high-end coastal retreats define luxury villas and vacation homes across the Caribbean. From the dramatic volcanic peaks of St. Lucia’s Pitons to the powdery white sands of Turks and Caicos, compare top listings to secure an unforgettable tropical escape.

Wonderful 4br And 3ba Villa Heated Pool Near Beach - Caribbean
No reviews

Wonderful 4br And 3ba Villa Heated Pool Near Beach

house, Hollywood
House rental listing. This accommodation is based in Hollywood.
Facilities and services include a terrace, a fridge and free parking. Enjoy a swimming pool in this house in Hollywood!
Luxury Tropical Oasis-4 Bedrm Private Pool Retreat - Caribbean
9.3 3 reviews

Luxury Tropical Oasis-4 Bedrm Private Pool Retreat

house, San Carlos Park
This 2-bedroom vacation home in Fort Myers offers a welcoming retreat, situated approximately 8.7 miles from Southwest Florida International Airport and 16 miles from Silverspot Cinema.
Enjoy exclusive access to a private pool with garden views, a fully equipped kitchen, and outdoor dining on the terrace, making this a perfect villa for your San Carlos Park holiday home experience.
Villa Indigo Pearl, Luxury, Orient Bay Seaview - Caribbean
No reviews

Villa Indigo Pearl, Luxury, Orient Bay Seaview

house, Orient Bay
Located in Orient Bay, Villa Indigo Pearl is a 17-minute walk from Orient Bay Beach and 1.9 miles from Grand Case-Espérance Airport, offering spectacular seaviews from this luxurious villa.
This spacious 3010 square feet holiday home features 3 bedrooms, 3 bathrooms, and accommodates up to 9 guests with a private swimming pool, fully equipped kitchen, air conditioning, and concierge services.
Las Olas Zen Home With Pool And Hot Tub Near Beach - Caribbean
No reviews

Las Olas Zen Home With Pool And Hot Tub Near Beach

house, Fort Lauderdale
Vacation rental listing. Your accommodation will be located in Fort Lauderdale.
Facilities and services: air conditioning, an iron and a washing machine. This house in Fort Lauderdale also has a terrace!

Villas in Caribbean with private pool

A private pool offers a tranquil space to swim and unwind on your own schedule after a day out on the water. Filter by price and location across leading booking sites to find your ideal poolside retreat, whether nestled in lush hillside gardens or overlooking clear turquoise bays.

Sol Del Este Luxury By Sh - Caribbean
10 1 review

Sol Del Este Luxury By Sh

house, San Andrés
This recently renovated two-bedroom villa is located in San Andrés, just 1.2 miles from San Luis Beach and 6.2 miles from the international airport, with close proximity to San Andres Bay and Morgan's Cave.
Offering 650 square feet of living space, this family-friendly holiday home accommodates up to four guests with a fully equipped kitchen, air conditioning, a private swimming pool, and a spacious garden, perfect for enjoying scuba diving and surfing opportunities nearby.
Beautiful Villa Sea View - Caribbean
10 2 reviews

Beautiful Villa Sea View

house, Boca Chica
Just 4 minutes from the beach, this 2-bedroom, 1-bathroom villa in Boca Chica offers a prime location near Alcazar de Colon and Coral Mall, perfect for exploring cultural sites and shopping.
This welcoming holiday home boasts a private rooftop jacuzzi for six, two communal swimming pools, and an on-site restaurant with sea views, ensuring a comfortable and convenient stay with excellent user ratings.
Chef Included - Fantasia Villas: Manoir De Lorient - Caribbean
No reviews

Chef Included - Fantasia Villas: Manoir De Lorient

house
Villa Manoir De Lorient is an authentic 18th-century French manor, authentically transported from Normandy, situated in Lorient, mere steps from Lorient Beach and a short distance from St. Jean Beach.
This luxurious villa offers 4840 square feet of living space, featuring a professional kitchen, a spacious living room opening onto a furnished terrace, a mezzanine relaxation area, and a tropical garden terrace with a swimming pool, making it an ideal holiday home and beach house.
Boca Chica, Tropical Paradise - Caribbean
No reviews

Boca Chica, Tropical Paradise

house, Boca Chica
Just 500 feet from Bocachica Beach, this welcoming villa offers prime access to Boca Chica's dining, bars, and supermarkets.
This 540 sq ft holiday home features 2 bedrooms and 2 bathrooms, accommodating up to 6 guests with air conditioning, a full kitchen, swimming pool, and garden, and includes a designated outdoor smoking area.

Frequently Asked Questions about Caribbean

  • What are the must-see attractions that I should visit in the Caribbean?

    When exploring the Caribbean, several attractions stand out. In Barbados, a visit to Harrison's Cave offers a chance to see impressive stalactites and stalagmites. For those in Jamaica, Dunn's River Falls provides a natural wonder where you can climb alongside cascading water. St. Lucia's iconic Pitons, two volcanic spires, are a breathtaking sight and a UNESCO World Heritage site. In Puerto Rico, the El Yunque National Forest is the only tropical rainforest in the U.S. National Forest System and features waterfalls and diverse plant life.
  • How much does it typically cost to stay in a villa in the Caribbean?

    The cost of a villa in the Caribbean can vary quite a bit, generally ranging from around $1,500 per week for a smaller, more basic option to $10,000 or more for a large, luxurious property with amenities like a private pool and staff. Factors like the island, the size of the villa, its proximity to the beach, and the time of year all play a significant role in pricing. During peak season, expect higher rates.
  • What are the best towns, villages, or areas to rent a villa in the Caribbean?

    For villa rentals, many travelers favor areas known for their beautiful beaches and amenities. In Turks and Caicos, Grace Bay is a popular choice for its stunning beach and upscale villas. Barbados offers options in areas like St. James, known for its platinum coast and elegant properties. St. Barts is renowned for its high-end villas and exclusive atmosphere. For a more laid-back vibe, consider areas in Antigua like Jolly Harbour.
  • When is the best time to book a villa in the Caribbean, and how far in advance should I plan?

    Booking a villa in the Caribbean is generally best done well in advance, especially for popular islands and during peak travel times. Planning six to twelve months ahead is advisable for the winter season, which runs from mid-December to mid-April, as this is when many people seek warmer climates. For the shoulder seasons, like late spring or fall, three to six months in advance might suffice, offering potentially better availability and prices.
  • What are the must-see festivals or seasonal events in the Caribbean?

    The Caribbean hosts vibrant festivals throughout the year. Carnival is a major event celebrated across many islands, with spectacular parades and music, notably in Trinidad and Tobago and Barbados (Crop Over). In December, many islands observe Christmas and New Year's with local celebrations and fireworks. The St. Lucia Jazz & Arts Festival, typically held in late April or early May, attracts international artists and showcases local talent.

Villas in Popular Destinations

Pet-friendly villas and vacation homes in Caribbean

Enjoy total peace of mind with fenced yards, spacious single-story layouts, and flexible outdoor spaces that make traveling with pets hassle-free. From quiet island nature paths to dog-approved coastal stretches, search pet-friendly villas and homes so your whole household can join the trip.

Casa Playa Arreboles Is Located In Front Of The Beach, Ideal For Families. - Caribbean
10 2 reviews

Casa Playa Arreboles Is Located In Front Of The Beach, Ideal For Families.

cottage, La Boquilla
Directly on the beach in La Boquilla, this welcoming cottage is just a short walk from La Boquilla Beach and a 17-minute drive from Clock Tower.
This spacious 1940 sq ft villa offers 5 bedrooms and 3.5 bathrooms accommodating up to 18 guests, featuring a private swimming pool, garden, terrace, and on-site parking, with abundant nearby activities like windsurfing, ecotours, and jet skiing.
Hidden Oasis 3 Blocks From Duval - Caribbean
9.6 102 reviews

Hidden Oasis 3 Blocks From Duval

cottage, Key West
Located in Key West's city center, this Conch-style cottage is just two blocks from Duval Street and within walking distance of the Ernest Hemingway Home and Museum and Southern Point.
This 530 sq ft cottage offers a private bedroom with a king bed and a living room with a queen sleeper sofa, sleeping up to 4 guests, and features a full kitchen, in-unit laundry, and shared access to a heated pool, making it an ideal holiday home.
Torre Alta I Bebroom House - Caribbean
No reviews

Torre Alta I Bebroom House

house, Manzanillo
Tranquil and comfortable, this 1-bedroom, 1-bathroom villa is located in the Torre Alta residential area of Puerto Plata, offering a peaceful retreat just a short distance from the airport and Malecon, with beaches approximately 25 minutes away by car.
This welcoming holiday home provides 810 square feet of living space, ideal for up to 2 guests, and features air conditioning, a kitchen with a fridge and microwave, a garden, and parking.
Amazing Private Cosy House, Fenced Yard, New, Pets - Caribbean
9.4 20 reviews

Amazing Private Cosy House, Fenced Yard, New, Pets

cottage, Delray Beach
Just 0.6 miles northeast of Atlantic Avenue, this remodeled one-bedroom cottage offers a prime Delray Beach location, a 10-minute walk from the beach, dining, and shopping.
This welcoming holiday home, accommodating up to 3 guests, features a modern kitchen, air conditioning, a private fenced backyard with a gas BBQ, and convenient on-premises parking, making it an ideal beach house near Atlantic Avenue.

Family-friendly Caribbean villas

Practical benefits like multiple bedrooms, open gathering spaces, and full kitchens ensure everyone stays relaxed during group getaways and multi-generational vacations. Whether snorkeling along the barrier reef or exploring historic harbor towns, compare top rentals to book a comfortable family base.

Spacious Beautiful Villa 5 Minutes From Sosua Night Live And 10 From Cabarete. - Caribbean
No reviews

Spacious Beautiful Villa 5 Minutes From Sosua Night Live And 10 From Cabarete.

house, Sosúa
This villa is located in Sosúa, a short distance from Sosúa Beach and Kite Beach, with Laguna SOV and Fun City also nearby.
Offering 10 bedrooms and 10 bathrooms, this spacious accommodation for up to 20 guests features a private pool with Jacuzzi, a basketball court, and a backyard with a pool table and BBQ, making it ideal for large groups and events.
Beach House Getaway | Waterfront | Free Kayaks - Caribbean
9.9 223 reviews

Beach House Getaway | Waterfront | Free Kayaks

house, Duck Key
This waterfront villa on Duck Key offers convenient access to Bahia Honda State Park, located 35 miles away, with Islamorada 30 miles away and Key West 1 hour and 20 minutes away.
Enjoy nearly 900 sq. ft. of living space in this family-friendly holiday home, featuring 2 bedrooms, 2 bathrooms, and sleeping capacity for 6 guests, complete with 4 kayaks and expansive porches with water and sunset views.
New 4br W Pool Walk To Las Olas 5mins To Beach - Caribbean
No reviews

New 4br W Pool Walk To Las Olas 5mins To Beach

house, Fort Lauderdale
Vacation house rental. You will stay in Fort Lauderdale.
Facilities and services include free parking, a fridge and a swimming pool. Take advantage of the air conditioning in this house in Fort Lauderdale.
158 M² House ∙ 3 Bedrooms ∙ 6 Guests - Caribbean
10 3 reviews

158 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Island Walk
Located in the exclusive North Naples gated community of Carlton Lakes, this welcoming villa offers convenient access to Veterans Park and is a short 3-mile drive to local water parks.
This spacious 1690 sq ft holiday home accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a completely renovated interior with oak floors and quartz countertops, two lanais with diverse views, and access to extensive community amenities including tennis courts, a pool, and a fitness center.

Caribbean beachfront vacation homes

Step directly onto world-class shorelines to take in warm ocean breezes, gentle waves, and breathtaking tropical sunsets right outside your door. From iconic destinations like Seven Mile Beach to hidden island coves, compare oceanfront rentals to find a seaside stay at the best rate.

Bahamian Pine - Modern Beach Villa - Caribbean
10 31 reviews

Bahamian Pine - Modern Beach Villa

house
Rio Grande  Rio Mar Cluster 2,vista Del Mar- View - Caribbean
9.5 111 reviews

Rio Grande Rio Mar Cluster 2,vista Del Mar- View

house
Dream Villa For Groups · Pool, Bbq & Billiards - Caribbean
9.3 109 reviews

Dream Villa For Groups · Pool, Bbq & Billiards

house
Mercí Beach House_la Calma - Caribbean
9.9 37 reviews

Mercí Beach House_la Calma

house
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