Villas and Vaction Homes in Caribbean

1250230 Villas and Vacation Homes in Caribbean

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • hometogo
  • expedia
  • belvilla
  • villanovo
  • interhome
  • tripcom
Caribbean
Search for your vacation home
Price per night
Accommodation type
Rating

Best villa offers in Caribbean

Newly Renovated Cottage Steps From The Water - Caribbean
9.6 44 reviews
Caribbean
01/06 – 01/20
$252/nighttotal: $3528 (14 )

Newly Renovated Cottage Steps From The Water

2 2
cottage, Bimini
Offering an authentic Bimini island experience, this private, gated half-acre enclave in Alice Town, North Bimini, boasts 100 feet of waterfront with a private dock for boat docking up to approximately 30 feet, providing direct access for swimming and snorkeling just steps from your door.
This welcoming holiday home is a well-appointed 2-bedroom, 2-bathroom villa accommodating up to 5 guests, featuring a kitchen with a fridge and microwave, air conditioning, a terrace, garden, parking, and Starlink high-speed WIFI, perfect for enjoying spectacular sunrise, sunset, and moonrise views while remaining a short cart ride from Radio Beach, Alice Town attractions, and Resort World.
On Lake Istokpoga: Lorida Home W/ Lanai! - Caribbean
9.9 25 reviews
Caribbean
08/20 – 08/24
$242/nighttotal: $968 (4 )

On Lake Istokpoga: Lorida Home W/ Lanai!

2 3
house, Lake Placid
This Lorida holiday home is located directly on Lake Istokpoga, offering lake views and a tranquil setting, 28 miles from Avon Square and 29 miles from the City of Avon Park Depot Museum.
This 1220 square foot villa features 2 bedrooms, 2 bathrooms, a private terrace, and a lanai, along with complimentary private parking and free WiFi for guest convenience.
C'renity Villa - Caribbean
9.2 53 reviews
Caribbean
08/27 – 09/05
$238/nighttotal: $2142 (9 )

C'renity Villa

1 2
house, Cul de Sac
C'RENITY VILLA is located in Cul de Sac, just 0.6 miles from Grand Case-Espérance Airport and 1.2 miles from Orient Bay Beach, offering a prime location for travelers.
This luxurious 1-bedroom villa boasts 1350 square feet of living space, an infinity pool, a hot tub, and a private balcony with sea views, accommodating up to 2 guests for a perfect holiday home experience.
Lodge ∙ 3 Bedrooms ∙ 8 Guests - Caribbean
Caribbean
10/19 – 10/23
$120/nighttotal: $480 (4 )

Lodge ∙ 3 Bedrooms ∙ 8 Guests

3 8
chalet
Located in a quiet area of the Dominican Republic, this chalet offers a serene retreat close to local amenities and natural surroundings.
This welcoming villa accommodates up to 8 guests with 3 bedrooms and 2 bathrooms, featuring a private swimming pool, a fully equipped kitchen with a microwave and oven, air conditioning, complimentary Wi-Fi, and a BBQ grill for outdoor gatherings.
La Posada Mountain Retreat In The Heart Of Puerto Rico With Exceptional Views - Caribbean
9.8 48 reviews
Caribbean
08/27 – 09/05
$168/nighttotal: $1512 (9 )

La Posada Mountain Retreat In The Heart Of Puerto Rico With Exceptional Views

1 2
chalet, Utuado
Centrally located in Utuado, Puerto Rico, this chalet offers spectacular mountain views and is conveniently situated approximately 30 minutes from the Indian Ceremonial Grounds, numerous rivers and waterfalls, and beaches and outlet malls.
This luxurious 1100 sq ft one-bedroom chalet accommodates up to 4 guests with a full kitchenette, private bathroom, air conditioning, and exclusive use of a heated infinity pool overlooking the mountains, alongside access to a garden with fruit picking and optional VIP tour packages.
Spacious  Ocean Front Property-rum Point Drive W/private Beach. Pet Friendly.... - Caribbean
9.6 76 reviews
Caribbean
10/19 – 10/23
$710/nighttotal: $2840 (4 )

Spacious Ocean Front Property-rum Point Drive W/private Beach. Pet Friendly....

3 8
cottage, North Side
Directly situated on 185 feet of pristine beach in North Side, this exclusive villa is a short drive from the Queen Elizabeth Botanical Gardens and the Mastic Trail, offering a truly exceptional holiday home experience.
This spacious 1910 square foot beach house boasts 3 bedrooms and 2 bathrooms, comfortably accommodating up to 9 guests with a fully equipped kitchen, a master suite featuring a jetted tub, and a large screened patio perfect for enjoying ocean breezes.
Shorline Cottages - Caribbean
10 2 reviews
Caribbean
11/30 – 12/31
$206/nighttotal: $6386 (31 )

Shorline Cottages

1 2
cottage, Rock Sound
Directly on the water in Tarpum Bay, this cottage offers ocean sounds and smells, a veranda for sunset viewing, and a pier for dining and night fishing, just a short drive from Powel Point Marina and Cotton Bay Club Golf Course.
This 950 sq ft cottage, accommodating up to 4 guests, features air conditioning, a jacuzzi, a garden, and parking, with easy access to water activities like kayaking and snorkeling, making it an ideal holiday home.
Indigo Reef #10 - Sunset Bay - Luxury Waterfront Villa, 31' Dock - Caribbean
Caribbean
12/19 – 12/26
$565/nighttotal: $3955 (7 )

Indigo Reef #10 - Sunset Bay - Luxury Waterfront Villa, 31' Dock

3 4
house, Marathon
Located in Marathon, this luxury waterfront villa boasts a 31' dock with sea views and is an 8-minute walk from Florida Keys Aquarium Encounters and one mile from Captain Hook S Marina Dive Center.
This 1600 sq ft holiday home features 3 bedrooms, 2 bathrooms, and accommodates up to 15 guests, offering a swimming pool, spa center, fitness center, and on-site parking.
Casa Madeira 2@ The Heart Of Miami Design District - Caribbean
9.7 131 reviews
Caribbean
08/20 – 08/24
$244/nighttotal: $976 (4 )

Casa Madeira 2@ The Heart Of Miami Design District

2 3
house, Miami
Located in Miami's Design District, Casa Madeira 2 offers a prime position, just 2.5 miles from the Adrienne Arsht Center and 2.9 miles from the American Airlines Arena.
This welcoming villa features a private patio and garden, a fully equipped kitchen with a dishwasher, and provides free private parking, making it an excellent holiday home option with a spa and babysitting service available.
Blue Mountains Jamaican Vacation - Caribbean
Caribbean
08/20 – 08/24
$208/nighttotal: $832 (4 )

Blue Mountains Jamaican Vacation

3 3
cottage, St Peters
Experience Jamaica's Blue Mountains from this eco-friendly cottage situated in Silver Hill Gap, a rural setting offering natural beauty and proximity to the Blue and John Crow Mountains National Park and Catherine's Peak, just a 7-minute walk from a river with natural pools and waterfalls.
This family-friendly villa accommodates up to 6 guests with 3 bedrooms and 1 bathroom, providing a fully self-sustained experience complete with a kitchen, terrace, garden, and parking, alongside opportunities for coffee farm tours and enjoying organic fresh fruit and herbs.
Prime Negril Location - 2br Brand New Apartment. New Water Tank Installed. - Caribbean
Caribbean
08/27 – 09/05
$113/nighttotal: $1017 (9 )

Prime Negril Location - 2br Brand New Apartment. New Water Tank Installed.

1 2
cottage, Negril
Centrally located in Negril's peaceful West End district, this cottage is just a 10-minute walk to the town square and a 15-minute walk to Negril's public beach, offering killer ocean views and convenient access to a pastry shop next door and Sunshine Plaza within a 2-minute walk.
This welcoming holiday home features 2 bedrooms, accommodating up to 4 guests, and includes essential amenities like air conditioning, a kitchen with a fridge and microwave, and a terrace, making it an ideal villa for your Negril getaway.
Little Blue Shack\ntiny House\nfully Equipped - Caribbean
10 2 reviews
Caribbean
07/01 – 07/08
$190/nighttotal: $1330 (7 )

Little Blue Shack\ntiny House\nfully Equipped

1 2
cottage, Culebra
Located in Culebra's Villa Flamenco neighborhood, this cottage is a 3-minute drive from Flamenco Beach and a 7-minute walk from the airport and transportation rentals.
This 1-bedroom, 1-bathroom cottage offers a 20 sq ft floor area, accommodates 2 guests, and includes a kitchen with a fridge and microwave, air conditioning, a terrace, garden, parking, and complimentary Wi-Fi, making it an ideal holiday home for exploring Culebra.

Villas and Vacation Homes with Pool in Caribbean

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

Marina View Cottage At Key Largo - Caribbean
9.8 9 reviews
Caribbean
08/27 – 09/05
$241/nighttotal: $2169 (9 )

Marina View Cottage At Key Largo

2 2
cottage, Key Largo
Directly on the marina in Key Largo, this waterfront cottage offers direct marina views and is located just 2 minutes from major shopping centers like TJ Maxx, Burlington, and Publix.
This welcoming 2-bedroom, 1-bathroom holiday home sleeps up to 6 guests and features a swimming pool, jacuzzi, air conditioning, and a fully equipped outdoor kitchen, making it an ideal villa for exploring nearby John Pennekamp Coral Reef State Park and Dagny Johnson Key Largo Hammock Botanical State Park.
Villa Euphyllia - Luxury Living By The Sea - Caribbean
Caribbean
06/20 – 06/27
$733/nighttotal: $5131 (7 )

Villa Euphyllia - Luxury Living By The Sea

1 2
house, Oyster Pond
Just a 4-minute walk from Coralita Beach, Villa Euphyllia is perfectly situated in Oyster Pond, 5.6 miles from Grand Case-Espérance Airport, offering a prime location for your getaway.
This welcoming villa accommodates up to 19 guests with 3 bathrooms, featuring a private balcony, terrace, air conditioning, and complimentary high-speed WiFi for a comfortable holiday home experience.
Caribbean Villa / Private Pool And Jacuzzi / 200m From Las Ballenas Beach / Wifi - Caribbean
9.7 122 reviews
Caribbean
08/14 – 08/21
$260/nighttotal: $1820 (7 )

Caribbean Villa / Private Pool And Jacuzzi / 200m From Las Ballenas Beach / Wifi

3 2
house, Las Terrenas
Just 200 meters from Las Ballenas Beach, this 3-bedroom villa offers a prime location within an intimate and secure residence in Las Terrenas, providing convenient beach access and proximity to attractions like Cayos Las Ballenas and shopping centers such as Plaza Rosada.
This welcoming holiday home boasts 1830 square feet of living space, featuring an open-plan ground floor with a fully equipped kitchen, living, and dining area, a private pool, jacuzzi, and is equipped with a power inverter for continuous electricity, accommodating up to 6 guests.
Comfortably Chic Pool Home Retreat - Caribbean
9.7 153 reviews
Caribbean
10/19 – 10/23
$486/nighttotal: $1944 (4 )

Comfortably Chic Pool Home Retreat

3 8
house, Naples
Located in Naples, this property is conveniently situated 3.3 miles from Tin City, 1.5 miles from the Collier Museum Of The Everglades, and 2.5 miles from Naples Municipal Airport.
This 1800 sq ft villa offers a private outdoor sanctuary with a year-round pool, garden, and children's playground, alongside a fully equipped kitchen, two living rooms, and soundproofed rooms for a peaceful stay.
Villa Azul Círculo Auto - Caribbean
Caribbean
11/09 – 11/16
$266/nighttotal: $1862 (7 )

Villa Azul Círculo Auto

1 2
chalet, Jarabacoa
Villa azul círculo auto in Jarabacoa offers a tranquil garden setting, featuring a private balcony and complimentary WiFi throughout the property, conveniently located 28 miles from Cibao International Airport and 10 miles from Salto de Jimenoa.
This family-friendly chalet accommodates up to 19 guests with 3 bathrooms, air conditioning, a fully equipped kitchen, and a swimming pool, providing a comfortable holiday home experience with personalized host management.
Home W Private Hot Tub, Near Everything In Sosua Center - Caribbean
Caribbean
01/06 – 01/20
$60/nighttotal: $840 (14 )

Home W Private Hot Tub, Near Everything In Sosua Center

1 2
house, Sosúa
Just a 7-minute walk from Alicia Beach and conveniently located near Sosúa Center, this villa offers a private entrance and is 4.3 miles from Gregorio Luperón International Airport.
This 1180 square foot holiday home features a private hot tub, access to an indoor pool and water park, a well-equipped kitchen, and complimentary Wi-Fi, providing a comfortable and entertaining stay.
Beautiful Island Home Away From Home. - Caribbean
9.6 87 reviews
Caribbean
10/19 – 10/23
$532/nighttotal: $2128 (4 )

Beautiful Island Home Away From Home.

4 8
apartment, Fort Pierce
Located on Hutchinson Island in Fort Pierce, this welcoming villa is just a few miles from Fort Pierce Inlet, offering prime access for beachgoers and water sports enthusiasts.
This spacious holiday home accommodates up to 8 guests with 4 bedrooms, 2 bathrooms, and features a fully equipped kitchen, air conditioning, a swimming pool, and a garden, with beach amenities provided for your convenience.
Landing View Villa 302 3br In The Heart Of Puntas - Caribbean
9.7 142 reviews
Caribbean
01/06 – 01/20
$258/nighttotal: $3612 (14 )

Landing View Villa 302 3br In The Heart Of Puntas

3 2
house, Puntas
Steps from world-famous Sandy Beach, this 3-bedroom villa in Rincon's Puntas district offers prime access to local beaches, restaurants like Tamboo and Casa Verde, and boutiques, making it an ideal beach house for your holiday home needs.
This expansive 2300 sq ft property comfortably accommodates up to 7 guests with three bedrooms, four bathrooms, a fully-equipped kitchen, and an 800 sq ft furnished roof deck with ocean views, complemented by communal outdoor amenities and convenient access to surfing, snorkeling, and deep-sea fishing.

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

copyright © 2026 villapicker.com