Villas and Vaction Homes in Caribbean

1250230 Villas and Vacation Homes in Caribbean

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Caribbean
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Best villa offers in Caribbean

Relax & Enjoy The Peace & Quiet At This Beachfront Home That Sleeps Up To 8 - Caribbean
8.0 2 reviews
Caribbean
06/19 – 06/27
$382/nighttotal: $3056 (8 )

Relax & Enjoy The Peace & Quiet At This Beachfront Home That Sleeps Up To 8

3 6
cottage, Cat Island
Directly on 150 feet of private white and pink sand beach on the Exuma Sound side of Cat Island, this cottage in Hawks Nest is a short distance from the Hermitage of Father Jerome and offers easy access to Mermaid Hole and Fernandez Bay.
This welcoming beach house accommodates up to 8 guests with 3 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, multiple decks for relaxation and grilling, and a separate bunkhouse, making it an ideal holiday home for exploring the island's natural attractions and activities like birdwatching.
Twin Palm Cottage - Caribbean
10 3 reviews
Caribbean
10/02 – 10/16
$193/nighttotal: $2702 (14 )

Twin Palm Cottage

2 2
cottage, Fort Myers
Located in Fort Myers' Sunset Park, this welcoming cottage offers easy access to the downtown historic district, including popular bars and restaurants, and is just a short drive to Key West Express and Fort Myers Country Club.
This family-friendly holiday home features 2 bedrooms, 1 bathroom, and accommodates up to 4 guests, boasting a private garden, terrace, air conditioning, and a full kitchen with a fridge, microwave, and dishwasher, making it an ideal villa for exploring Fort Myers.
Villamerissa Nestled Between Two Unspoiled Beaches Pool/jacksprat/wifi/gym/staff - Caribbean
9.7 37 reviews
Caribbean
05/09 – 05/18
$735/nighttotal: $6615 (9 )

Villamerissa Nestled Between Two Unspoiled Beaches Pool/jacksprat/wifi/gym/staff

6 2
apartment, Treasure Beach
Perfectly positioned between two unspoiled Caribbean beaches, this apartment in Treasure Beach offers immediate access to swimming, snorkeling, and kayaking, and is a short walk from popular spots like Jack-Sprat, supermarkets, shops, bars, and the Treasure Beach Sports Park.
This welcoming villa boasts a private rooftop terrace with a plunge pool, gazebo bar, and yoga space providing 360-degree ocean and mountain views, along with a range of family-friendly amenities and optional services including airport transfers and personal chef.
Faroway Luxury Villa - Caribbean
Caribbean
06/19 – 06/27
$3246/nighttotal: $25968 (8 )

Faroway Luxury Villa

1 6
house, Half Way Pond
Faroway Luxury Villa is situated 3.1 miles from Owen Roberts International Airport, offering an exclusive retreat in the Half Way Pond area of the Cayman Islands.
This expansive 5010 square foot villa provides accommodation for up to 15 guests with 5 bathrooms, featuring a private entrance, air conditioning, a well-equipped kitchen with a dishwasher and microwave, cable TV, an outdoor swimming pool, and garden relaxation opportunities.
Oceanpointe Villa, Brand New, Clean, Cottage With All The Resort Amenities. - Caribbean
Caribbean
05/08 – 05/15
$285/nighttotal: $1995 (7 )

Oceanpointe Villa, Brand New, Clean, Cottage With All The Resort Amenities.

2 3
cottage, Lucea
Offering private beach access and nestled in the mountains by a river, this Lucea cottage is located across the street from the Grand Palladium resort, approximately 35 miles from Montego Bay airport and 50 miles from Negril.
This welcoming 2-bedroom, 2-bathroom villa accommodates up to 4 guests and features a kitchen with a fridge and microwave oven, air conditioning, a swimming pool, terrace, garden, fitness center, tennis court, and parking, with breakfast included.
Dalkeith Cottages-peacocks And Saltwater Pool - Caribbean
Caribbean
05/02 – 05/08
$152/nighttotal: $912 (6 )

Dalkeith Cottages-peacocks And Saltwater Pool

1 3
cottage, Knockpatrick
Located in the cool parish of Manchester, this former colonial plantation, Dalkeith Great House, is just a 10-minute drive from Mandeville town, offering a peaceful retreat with a rich history.
This welcoming cottage offers 1 bedroom and 1 bathroom, accommodating up to 3 guests with amenities including air conditioning, a fridge, microwave oven, and access to a swimming pool and garden, making it an ideal holiday home in the area.
Pondside Retreat At Flitterbug Farm - 3br/2ba - Dog Friendly - Caribbean
10 3 reviews
Caribbean
07/14 – 07/18
$239/nighttotal: $956 (4 )

Pondside Retreat At Flitterbug Farm - 3br/2ba - Dog Friendly

3 6
farm, LaBelle
Flitterbug Farm, a unique three-bedroom villa in LaBelle, offers a peaceful retreat near Okaloacoochee Slough State Forest and Jim Fleming Ecological Park, with Florida Ridge AirSports Park and Veterans Park also in the vicinity.
This welcoming holiday home provides a dedicated camping area with a heated outdoor shower, a fire pit, a large fenced-in backyard, and expansive green space perfect for enjoying South Florida sunsets and stargazing, accommodating up to 8 guests with internet and air conditioning.
Sand Dollar Jenson Beach Home With Pool Access! - Caribbean
9.9 85 reviews
Caribbean
10/02 – 10/16
$213/nighttotal: $2982 (14 )

Sand Dollar Jenson Beach Home With Pool Access!

2 2
house, Jensen Beach
Conveniently located in Jensen Beach, this welcoming villa is a mere 16-minute walk to Jensen Beach and situated 16 miles from Fort Pierce City Marina and 20 miles from Fort Pierce Inlet State Park.
This 1510 square feet holiday home offers air conditioning, a swimming pool, a garden, a tennis court, and a fully equipped kitchen, making it an excellent choice for families and pet owners looking for a comfortable stay near the Jensen Beach To Jupiter Inlet Aquatic Preserve.
Coastal Farmhouse With Mini Golf, Private Beach &Spa - Caribbean
9.8 21 reviews
Caribbean
05/08 – 05/15
$227/nighttotal: $1589 (7 )

Coastal Farmhouse With Mini Golf, Private Beach &Spa

2 3
house, Naples
This welcoming villa in Naples offers direct access to a private beach and is located 1.8 miles from the Naples Museum of Art and 4.6 miles from Tin City.
Enjoy 860 square feet of living space, accommodating up to 7 guests with 2 bedrooms, a fully equipped kitchen, a Jacuzzi, a private spa area, and complimentary bikes for exploring the area.
Palm Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated! - Caribbean
9.8 53 reviews
Caribbean
05/08 – 05/15
$299/nighttotal: $2093 (7 )

Palm Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated!

1 3
cottage, Cudjoe Key
This cottage is located on Summerland Key, a 2-minute walk from Tonio's Tiki Bar and a 15-minute drive to Bahia Honda State Park, with Key West 25 miles away.
This 480 sq ft holiday home features a full kitchen, a walk-in shower, and sleeps up to 4 guests, offering complimentary laundry facilities, a private outdoor seating area, and access to communal resort amenities including a pool and gas grill, making it an ideal villa for a relaxing getaway.
Unique Hilltop Eco Villa, Las Terrenas W/housekeeper, Featured In Dwell Magazine - Caribbean
9.6 30 reviews
Caribbean
10/31 – 11/07
$657/nighttotal: $4599 (7 )

Unique Hilltop Eco Villa, Las Terrenas W/housekeeper, Featured In Dwell Magazine

5 12
house, Las Terrenas
Perched in the mountains near Las Terrenas, this eco-villa offers stunning views of the Samana Peninsula, with Punta Popy and Coson beaches a five-minute drive away and Cayos Las Ballenas attractions a fifteen-minute drive.
This luxurious 4000 sq ft villa, inspired by Le Corbusier's Villa Savoye and powered by solar energy and rainwater, features five bedrooms, three bathrooms, an infinity pool, a rooftop patio, and can accommodate up to 12 guests with included weekday housekeeping.
Quiet Ocean Front Paradise In Bonaire - Caribbean
10 68 reviews
Caribbean
05/08 – 05/15
$727/nighttotal: $5089 (7 )

Quiet Ocean Front Paradise In Bonaire

4 3
apartment, kralendijk
Ocean Front House KR14 is an oceanfront villa located in Hato, Bonaire, just a 5-minute drive from downtown Kralendijk and a 10-minute drive from the airport, offering direct oceanfront access with a private beach and a staircase to the coral reef for swimming, scuba diving, and snorkeling.
This spacious 2690 square foot holiday home features 4 bedrooms, 4 bathrooms, a private pool, a lush tropical garden, a studio apartment for enhanced privacy, and an outdoor mini kitchen with a grill, perfect for al fresco dining on the large oceanfront terrace with panoramic ocean views.

Villas and Vacation Homes with Pool in Caribbean

Among the 1250230 villas in Caribbean here are the 8 best villas with pool

New 2 Br Villa W/pool & Rooftop - Caribbean
10 36 reviews
Caribbean
05/08 – 05/15
$152/nighttotal: $1064 (7 )

New 2 Br Villa W/pool & Rooftop

2 3
house, Sosua
Villa OMI is located in the newly developed section of Sosua Ocean Village, a secure, gated community less than 20 minutes from Puerto Plata Airport.
This exclusive villa offers a private pool with a terrace, a rooftop sundeck with dining space, and luxurious Zen-like interiors, accommodating up to 4 guests with two ensuite bedrooms and access to community amenities like a waterpark and restaurants.
Villa Bayacanes Con Piscinas Privadas - Caribbean
9.8 36 reviews
Caribbean
06/19 – 06/27
$428/nighttotal: $3424 (8 )

Villa Bayacanes Con Piscinas Privadas

4 6
house, Jarabacoa
Villa Bayacanes in Jarabacoa is located 16 miles from Salto de Jimenoa and 20 miles from Monumento a los Heroes de la Restauracion, offering excellent mountain views and a prime location for exploring natural attractions.
This spacious 1550 square feet villa features 4 bedrooms, 3 living rooms, and 4 bathrooms, including a hot tub, along with a private swimming pool, jacuzzi, bar, and family-friendly amenities, providing a luxurious holiday home experience with convenient access to Cibao International Airport.
Amazing Villa With Pool Just 20 Minutes From The Airport! - Caribbean
10 2 reviews
Caribbean
06/19 – 06/27
$119/nighttotal: $952 (8 )

Amazing Villa With Pool Just 20 Minutes From The Airport!

3 6
house, Santo Domingo Este (Zona Urbana)
Located in Los Frailes, Santo Domingo Este, this villa is approximately 35 miles from popular beaches and offers convenient access to landmarks like El Obelisco and Colon Lighthouse and Museum, with Coral Mall and Cuadra San Isidro Shopping Center just a short drive away.
This family-friendly holiday home accommodates up to 7 guests with 3 bedrooms and 2 bathrooms, featuring a private swimming pool with a children's area, air conditioning, high-speed Wi-Fi, and a fully equipped kitchen, all while ensuring essential power with an electric inverter.
Villa Gogorobi Mit Privatem Pool - Caribbean
Caribbean
06/15 – 06/20
$157/nighttotal: $785 (5 )

Villa Gogorobi Mit Privatem Pool

3 2
house, Willemstad
Located east of Willemstad in the Kwarchi neighborhood of Villapark Flamboyan, this secluded luxury villa is just 1.5 miles from the Sint Jorisbaai nature reserve and a short drive to popular beaches such as Santa Barbara, Jan Thiel, and Mambo Beach.
This recently renovated 1,570 sq ft house offers 3 bedrooms and 2 bathrooms accommodating up to 6 guests, featuring a private pool with a deck, an outdoor kitchen with a gas BBQ, air conditioning, free WiFi, and is conveniently situated within a 15-minute drive of major supermarkets and downtown Willemstad.
Premier Host! 3br/3ba Villa W/ Private Pool Private Perla Marina Beach  Gated - Caribbean
9.7 112 reviews
Caribbean
05/25 – 05/31
$148/nighttotal: $888 (6 )

Premier Host! 3br/3ba Villa W/ Private Pool Private Perla Marina Beach Gated

3 2
apartment, Perla Marina
Located in the secure Perla Marina gated community, this villa offers exclusive access to a private beach just a 5-minute walk away and is 20 miles from Puerto Plata Airport, providing easy access to attractions like Ocean World Adventure Park and Amber Cove.
This spacious 2200 sq ft holiday home features 3 bedrooms and 3 bathrooms, a private pool, Jacuzzi, and an outdoor grilling area, perfect for families and groups seeking adventure activities such as kite surfing, diving, and horseback riding.
Villa With Pool Steps From The Buyé Beach - Caribbean
9.9 261 reviews
Caribbean
07/20 – 07/25
$205/nighttotal: $1025 (5 )

Villa With Pool Steps From The Buyé Beach

1 2
house, 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.
Beachfront Villa, Natural Pool, Billiards, Jacuzzi - Caribbean
10 10 reviews
Caribbean
10/31 – 11/07
$957/nighttotal: $6699 (7 )

Beachfront Villa, Natural Pool, Billiards, Jacuzzi

1 12
house, Juan Esteban
House listing for up to 14 people with an excellent rating of 100% based on 10 reviews. You will be based in Juan Esteban.
Services and facilities: a garden, a barbecue and a kitchen. Take a dip in the pool of this house in Juan Esteban!
Heated Pool / Las Olas / Victoria Park / Near Beach / Escapism At Its Finest / Mermaid Key - Caribbean
10 2 reviews
Caribbean
06/19 – 06/27
$1139/nighttotal: $9112 (8 )

Heated Pool / Las Olas / Victoria Park / Near Beach / Escapism At Its Finest / Mermaid Key

3 6
cottage, Fort Lauderdale
Located in Fort Lauderdale's Victoria Park, this Florida-style cottage is just 7 minutes by golf cart from the beach and steps from Las Olas Boulevard's shops and dining.
This welcoming villa offers 3 bedrooms, 3 bathrooms, and sleeps 10, featuring a private heated pool, jacuzzi, garden, and includes beach gear for a perfect holiday home experience.

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

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