Villas and Vacation Homes in Caribbean

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Caribbean

Best villa offers in Caribbean

Walk To Beach Luxury 5br & 3ba Villa Hollywood Lakes - Caribbean
No reviews

Walk To Beach Luxury 5br & 3ba Villa Hollywood Lakes

house, Hollywood
House listing. Your accommodation will be located in Hollywood.
Facilities and services include an iron, air conditioning and a fridge. Take advantage of the terrace in this house!
New Luxe Canal-front Cottage In The Bahamas!!! - Caribbean
No reviews

New Luxe Canal-front Cottage In The Bahamas!!!

cottage, Nassau
Just 500 feet from Cabbage Beach and Cable Beach, this welcoming cottage in Nassau offers direct access to a saltwater canal ideal for kayaking and snorkeling.
This exclusive villa boasts three living units, accommodating up to 14 guests with resort-style amenities including full kitchens, a private patio, and optional paid activities like private chef services, making it a perfect holiday home.
Farm House <Br>warm, Cozy And Full Of Charm - Caribbean
10 2 reviews

Farm House <Br>warm, Cozy And Full Of Charm

farm, Higüey
Located on the Matachalupe road in Higüey, this secluded rural manor house is just a short drive from local landmarks like Cueva de Berna and El Obelisco, offering a peaceful escape.
This family-friendly villa accommodates up to 10 guests with 3 bedrooms and 2 bathrooms, featuring a private swimming pool, air conditioning, a fully equipped kitchen, and a terrace, with convenient access to Caribbean Cinemas Multiplaza Higuey and Casa de Campo Marina.
Pennies From Heaven Cottage/ House,  #Cottage, #House - Caribbean
10 39 reviews

Pennies From Heaven Cottage/ House, #Cottage, #House

cottage, Rio
Located on a private street in Jensen Beach, this cottage offers St. Lucie River views and is just minutes from historic Jensen and Stuart town centers, providing easy access to dining, shopping, and cultural attractions.
This family-friendly villa boasts three bedrooms, two bathrooms, and a guest capacity of six, featuring a pirate ship play area, hot/cold outdoor shower, and a hidden master bath behind a sliding bookcase, making it an ideal holiday home with abundant entertainment options for a memorable stay.
Villa Whith Pool Steps From The Buye Beach - Caribbean
9.9 284 reviews

Villa Whith Pool Steps From The Buye Beach

cottage, Cabo Rojo
Directly across from the beautiful Buye Beach, this villa in Cabo Rojo offers exclusive, controlled access for a secure and luxurious coastal retreat.
This family-friendly holiday home provides hotel-like amenities including a private pool, air conditioning, Wi-Fi, and entertainment options, comfortably accommodating up to six guests.
Ego Guesthouse - Caribbean
9.5 53 reviews

Ego Guesthouse

house, Lucea
EGO GUESTHOUSE, a peaceful family-friendly villa, offers a private retreat in Lucea, Hanover Parish, Jamaica, powered by a sustainable solar energy system for year-round comfort.
This exclusive 2-bedroom, 2-bathroom villa accommodates up to 5 guests and features a private swimming pool, garden, fitness center, and convenient parking, ensuring a comfortable and enjoyable stay.
El Mogote's Switzerland - Caribbean
9.8 9 reviews

El Mogote's Switzerland

cabin, Jamao al Norte
Offering spectacular mogote views, this private mountain villa is located in Villa Trina, just a short distance from Jamao al Norte.
This exclusive villa accommodates up to 10 guests with 3 bedrooms and 4 bathrooms, featuring air conditioning, internet, a full kitchen, and parking, ensuring absolute tranquility perfect for family getaways and disconnecting in nature.
Downtown Stuart Coastal Cottage - Caribbean
9.9 97 reviews

Downtown Stuart Coastal Cottage

house, Stuart
Centrally located in Stuart, this coastal chic cottage is just steps from waterfront Hildebrad Park and one block from Cleveland Clinic North, providing easy access to downtown Stuart, beaches, shopping, and dining.
This remodeled 1190 sq ft villa accommodates up to 4 guests with 2 bedrooms, a fully equipped kitchen, and a screened-in patio, offering a welcoming holiday home experience near Savannas Preserve State Park and Seabranch Preserve State Park for outdoor adventures.

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.

Family Paradise With Heated Pool, 8 Min From The Beach - Caribbean
No reviews

Family Paradise With Heated Pool, 8 Min From The Beach

house, Pompano Beach
Vacation rental listing. You will be based in Pompano Beach.
Services and facilities: a kitchen, a fridge and free parking. This house in Pompano Beach also has air conditioning!
Luxury Villa With Pool, Beach & Pickleball Court At Seaglass Cove - Caribbean
No reviews

Luxury Villa With Pool, Beach & Pickleball Court At Seaglass Cove

house, Marathon
Located in a private community in Marathon, this luxury vacation home is 6.9 miles from Florida Keys Aquarium Encounters and 57 miles from Key West International Airport.
This exclusive 4950 sq ft villa offers beachfront property with private beach access, accommodating up to 19 guests with 5 bedrooms, 2 living rooms, 5 bathrooms, a swimming pool, garden, spa, and free WiFi.
Eagles Nest Villa House Ac Tv Wifi Fan Luxury Modern - Caribbean
9.8 6 reviews

Eagles Nest Villa House Ac Tv Wifi Fan Luxury Modern

house, Albion
Eagles Nest Villa is located in Albion, 15 miles from Norman Manley International Airport.
This recently renovated country house offers 1500 square feet of living space with 3 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, and a terrace with mountain views, making it an ideal holiday home for up to 15 guests.
5-star Lakefront Oasis In Hollywood-hard Rock Casino - Caribbean
No reviews

5-star Lakefront Oasis In Hollywood-hard Rock Casino

house, Dania Beach
Vacation house to rent. You will stay in Dania Beach.
Facilities and services include air conditioning, a dish washer and an iron.

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.

Bonita Golf Beach Getaway Luxe Condo By Naples - Caribbean
9.0 2 reviews

Bonita Golf Beach Getaway Luxe Condo By Naples

house, Bonita Springs
This welcoming villa in Bonita Springs is conveniently located 1.6 miles from Everglades Wonder Gardens and 8.7 miles from Delnor-Wiggins Pass State Park.
Boasting 15,070 square feet of living space, this holiday home accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen, air conditioning, a private swimming pool, jacuzzi, and access to a fitness center.
Rodriguez Home - Caribbean
9.6 15 reviews

Rodriguez Home

house, Bonao
Discover a newly constructed villa in Bonao, situated in a highly secure district with 24/7 security, providing a tranquil environment for your stay.
This family-friendly holiday home features 2 bedrooms, accommodating up to 6 guests, and offers amenities such as air conditioning, a full kitchen with a fridge, freezer, and microwave, a swimming pool, gym, and a playground.
Full Time Lic Mgr - Modern 3 Bed 4 Bath Villa - Upscale Oceanfront Resort - Indoor Pickleball - Spea - Caribbean
No reviews

Full Time Lic Mgr - Modern 3 Bed 4 Bath Villa - Upscale Oceanfront Resort - Indoor Pickleball - Spea

house, Key Largo
Vacation rental listing. Your accommodation will be located in Key Largo.
Facilities and services include an iron, a kitchen and a dish washer. Take advantage of the terrace in this house!
Private 8 Bedroom Villa - Caribbean
9.8 150 reviews

Private 8 Bedroom Villa

house, Noord overig
Sabana Liber, Noord, places you a short drive from the pristine sands of Eagle Beach and Palm Beach, and conveniently near theme parks and a water park for family fun.
This spacious 3-bedroom, 2-bathroom villa offers a large outdoor swimming pool, a generous BBQ area, and is equipped with air conditioning, internet, and a full kitchen, making it an excellent choice for a family-friendly holiday home.

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.

Spectacular Paradise In Juan Dolio, Luxury Pool - Caribbean
9.2 142 reviews

Spectacular Paradise In Juan Dolio, Luxury Pool

house, Juan Dolio
Located in Juan Dolio, this villa is conveniently situated approximately 15 miles from Las Américas Airport and 40 miles from downtown Santo Domingo.
This welcoming 4-bedroom, 2-bathroom holiday home comfortably accommodates up to 9 guests, featuring a majestic swimming pool, barbecue facilities, and a unique blend of rustic interior and beach villa exterior for a tranquil escape.
3 Mi To Jensen Beach: Pet-friendly Getaway W/ Yard - Caribbean
10 1 review

3 Mi To Jensen Beach: Pet-friendly Getaway W/ Yard

cottage, Jensen Beach
Conveniently located in Jensen Beach, this cottage is within 1 mile of Indian Riverside Park and The Children's Museum of the Treasure Coast, and within 3 miles of Savannas Preserve State Park and Harbour Bay Plaza.
This pet-friendly cottage offers a smoke-free environment with air conditioning, complimentary WiFi in public areas, and free self-parking, featuring a fully equipped kitchen with a microwave and dishwasher for a comfortable stay.
75 M² House ∙ 1 Bedroom ∙ 2 Guests - Caribbean
No reviews

75 M² House ∙ 1 Bedroom ∙ 2 Guests

house, Puerto Plata
Located in the tranquil residential area of Torre Alta, Puerto Plata, this welcoming villa is conveniently situated less than 1 mile from the airport and close to the popular Malecon waterfront promenade.
This holiday home offers 810 square feet of living space with air conditioning, a kitchen equipped with a fridge and microwave, and parking, accommodating up to 2 guests for a peaceful retreat.
Beach Cabin W/ Pool & Ocean Views + Breakfast - Caribbean
10 4 reviews

Beach Cabin W/ Pool & Ocean Views + Breakfast

cabin
Directly on a private beach in Barú, a coastal district of Cartagena, Colombia, this luxurious villa offers exclusive enjoyment and breathtaking ocean views.
This exceptional beach house, ideal for groups of up to 12, features 6 bedrooms, 5 bathrooms, air conditioning, a shared swimming pool, an on-site restaurant, and complimentary breakfast, making it a perfect venue for weddings and private retreats.

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.

Naples Calming Waves Luxury Home 4-3 - Caribbean
No reviews

Naples Calming Waves Luxury Home 4-3

house, Naples Park
This Naples Park villa offers a prime location, situated just 1.2 miles from Delnor-Wiggins Pass State Park and 1.6 miles from Vanderbilt Beach.
This spacious 2080 sq ft holiday home accommodates up to 19 guests with 4 bedrooms and 3 bathrooms, featuring a private pool, jacuzzi, spa, bar, tennis court, and barbecue facilities for an ultimate getaway.
Beach Farmstay Studio Room W Pool - Caribbean
9.8 218 reviews

Beach Farmstay Studio Room W Pool

farm
Located on the southeast coast of Puerto Rico, Finca Corsica is situated just 1.5 hours from San Juan and 1 hour from Ponce, offering direct access to an emerald-colored Caribbean beach a short stroll away.
This welcoming studio villa, accommodating up to 2 guests, features air conditioning, a kitchenette, a queen bed, and a private terrace, with communal access to a swimming pool, lush gardens, and a tranquil natural pool beside a scenic reserve.
Paradis Caché: Confort, Piscine, Nature Luxuriante - Caribbean
10 16 reviews

Paradis Caché: Confort, Piscine, Nature Luxuriante

house
Located in the highly desirable Orient Bay district, this welcoming villa is just 200 meters from the beach and a short walk to local shops and restaurants.
This spacious 4-bedroom holiday home accommodates up to 8 guests and boasts a large, secure swimming pool, a beautiful tropical garden, and air conditioning for a comfortable stay.
House ∙ 2 Bedrooms ∙ 4 Guests - Caribbean
No reviews

House ∙ 2 Bedrooms ∙ 4 Guests

house, Jensen Beach
Discover Nettles Island, a resort community on Hutchinson Island, offering exclusive ocean-to-river living just steps from the Atlantic Ocean beaches and the Indian River, providing a tranquil island vacation setting.
This welcoming 2-bedroom, 2-bathroom villa comfortably accommodates up to 4 guests and features access to community amenities including two junior Olympic-size pools, a fitness center, tennis courts, and a private marina.

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.

Soulace 445 B - Caribbean
No reviews

Soulace 445 B

house, Naples Park
Bright Home By The Beach With A Pool - 4 Bedrooms - Caribbean
9.6 69 reviews

Bright Home By The Beach With A Pool - 4 Bedrooms

house
Kc90 Vitamin Sea - Caribbean
10 2 reviews

Kc90 Vitamin Sea

house, Key Colony Beach
Lagun | Stunning Seafront Villa Near Playa Lagun - Caribbean
9.7 26 reviews

Lagun | Stunning Seafront Villa Near Playa Lagun

house, Lagun
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