Villas and Holiday Homes in Caribbean

1782394 Villas and Holiday Homes in Caribbean

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

Best villa offers in Caribbean

Villas and holiday homes with private pool in the Caribbean

Palm-fringed beaches and calm turquoise waters set the scene for our selection of villas with pool across the Caribbean. Compare holiday homes with pool to find the best stay.

3-br Gated Villa, Kitchen, Pool, Wi-fi, Ac - Caribbean
8.7 59 reviews

3-br Gated Villa, Kitchen, Pool, Wi-fi, Ac

house, Las Terrenas
Secluded and safe, this 3-bedroom villa in Las Terrenas is just a 300-meter walk from beautiful beaches and close to Pueblo de Los Pescadores, known for its restaurants and nightlife.
This spacious 205 square meter holiday home accommodates up to 8 guests and features a private swimming pool, a newly renovated kitchen and bathrooms, and offers opportunities for scuba diving, sailing, and horse riding nearby.
Tropical Getaway Pool And Tiki Bar - Caribbean
No reviews

Tropical Getaway Pool And Tiki Bar

house, Harbour Heights
House. You will be located in Harbour Heights.
Facilities and services include a washing machine, air conditioning and free parking. Enjoy a swimming pool in this house in Harbour Heights!
Casa Pitiusa  Piscina Y Terraza, Las Terrenas - Caribbean
10 1 review

Casa Pitiusa Piscina Y Terraza, Las Terrenas

house
Centrally located in Las Terrenas, this villa is a mere 300 meters from the nearest beach and within easy reach of local restaurants.
This holiday home offers accommodation for four guests with two bedrooms, two bathrooms, air conditioning, a private terrace, and access to a communal swimming pool, alongside a fully equipped kitchen and Wi-Fi.
Honeymoon-worthy W/ Pvt Pool Walk 2 Sapphire Beach - Caribbean
9.6 274 reviews

Honeymoon-worthy W/ Pvt Pool Walk 2 Sapphire Beach

house
Just 300 meters from Sapphire Beach, this private villa on St. Thomas offers direct walking access to its dining options and coffee spot, with the ferry terminal for St. John and the British Virgin Islands conveniently located nearby.
This luxury accommodation, a welcoming holiday home, features a well-equipped kitchen with a Weber grill, a king-sized bedroom with a spa-like bathroom, a spacious living area with a convertible sofa and Smart TV, and provided beach gear, making it ideal for up to 5 guests.

Villas and holiday homes by the sea in the Caribbean: sea view and coastal stays

Compare our holiday homes by the sea in the Caribbean, near Seven Mile Beach, from beachfront estates to properties with sweeping sea views. See our villa by the sea in the Caribbean.

Ohana House - Caribbean
9.2 33 reviews

Ohana House

house, San Andrés
Conveniently located just 1 kilometre from Gustavo Rojas Pinilla International Airport, this villa offers easy access to Los Almendros Beach, San Andres Bay, and North End, with The Hill 5.8 kilometres away and Morgan's Cave 6.4 kilometres distant.
This welcoming holiday home, spanning 80 square meters, accommodates up to 14 guests across 3 bedrooms and 2 bathrooms, featuring air conditioning, free WiFi, and a sun terrace, alongside bicycle parking and a tour desk.
Your Tropical Retreat In The Heart Of Boqueron, Wifi, Full A/c, Wi-fi, Sleeps 6 - Caribbean
9.8 193 reviews

Your Tropical Retreat In The Heart Of Boqueron, Wifi, Full A/c, Wi-fi, Sleeps 6

house, Boqueron
Directly in Boqueron Poblado, this villa offers immediate access to the town's attractions, situated just a short walk from Boqueron's beaches, pubs, bars, restaurants, and local shops in Cabo Rojo.
This welcoming holiday home boasts a private swimming pool and spa, comfortably accommodating up to six guests with its air-conditioned interior featuring a bedroom with two queen beds and a living area with a sleeper sofa, alongside a well-equipped kitchen and Wi-Fi.
South Hutchinson Island Cottage W/ Beach Access! - Caribbean
9.6 76 reviews

South Hutchinson Island Cottage W/ Beach Access!

house, Jensen Beach
Offering direct beach access, this South Hutchinson Island cottage in Jensen Beach is conveniently located 29 kilometres from Fort Pierce City Marina and 34 kilometres from Fort Pierce Inlet State Park.
This two-bedroom villa rental provides 74 square metres of floor area and features a private patio, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, air conditioning, a swimming pool, a garden, and a spa.
New 2 Br Villa W/pool & Rooftop - Caribbean
10 40 reviews

New 2 Br Villa W/pool & Rooftop

house
Located in the exclusive Sosua Ocean Village, this villa rental is less than 20 minutes from Puerto Plata Airport and situated in a newly developed section of the gated community, offering enhanced safety and privacy.
This luxurious holiday home boasts a private pool, a furnished rooftop sundeck with panoramic views, and two ensuite bedrooms, accommodating up to four guests with access to shared community amenities.

Frequently Asked Questions about Caribbean

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

    For a truly memorable experience in the Caribbean, consider visiting Dunn's River Falls in Jamaica, a stunning terraced waterfall you can climb. In Barbados, a visit to the historic Bridgetown and its Garrison offers a glimpse into colonial history. The Pitons in St. Lucia are iconic volcanic spires offering breathtaking views and excellent hiking opportunities. For underwater exploration, the vibrant coral reefs of Bonaire are a world-renowned diving destination.
  • How much does it typically cost to stay in a villa in the Caribbean?

    Villa rental costs in the Caribbean can vary significantly. A modest two-bedroom villa might range from $200 to $500 per night, while a larger, luxurious property with ocean views and amenities like a private pool could cost $1,000 to $5,000 or more per night. Prices are also influenced by the island, the season, and the specific features of the villa.
  • What are the best towns, villages, or areas to rent a villa in the Caribbean?

    For a diverse range of villa experiences, consider Grace Bay in Turks and Caicos for its pristine beaches and upscale offerings. St. Barts is known for its luxurious villas and exclusive atmosphere. In Antigua, English Harbour provides historical charm alongside beautiful bays. For a more laid-back vibe with stunning natural beauty, consider areas around Soufrière in St. Lucia.
  • When is the best time to book a villa in the Caribbean, and how far in advance should I plan?

    The peak season for the Caribbean is typically from mid-December to mid-April, which also means higher prices. For the best selection and potentially better rates, booking a villa six to nine months in advance is recommended, especially if traveling during this popular period. The shoulder seasons, from late April to June and again from September to November, can offer a good balance of pleasant weather and fewer crowds, with booking 3 to 6 months ahead often sufficient.
  • What are the must-see festivals or seasonal events in the Caribbean?

    The Caribbean hosts vibrant celebrations throughout the year. The Crop Over Festival in Barbados, typically held in July and early August, is a major summer festival with calypso music and parades. Carnival celebrations, particularly in Trinidad and Tobago in February or March, are world-famous for their elaborate costumes and energetic street parties. The St. Lucia Jazz & Arts Festival, usually held in late April or May, attracts international musicians.

Villas in Popular Destinations

Luxury villas and holiday homes in the Caribbean

Our platform brings together the finest luxury villas across the Caribbean, from private beaches to hidden coves. Discover your luxury holiday home.

Indigo Reef #57 - Turtle Cove - Luxury Waterfront Villa, 31' Dock - Caribbean
No reviews

Indigo Reef #57 - Turtle Cove - Luxury Waterfront Villa, 31' Dock

house, Marathon
Offering sea views and a private 31-foot dock, this luxury waterfront villa in Marathon is conveniently located just an 11-minute walk from Florida Keys Aquarium Encounters and 1.1 kilometres from Captain Hook's Marina Dive Center.
This spacious holiday home, spanning 149 square meters with three bedrooms and two bathrooms, accommodates up to 15 guests and features a private terrace, swimming pool, spa, fitness centre, and on-site parking.
Tropical Luxury Dreams - Caribbean
8.6 10 reviews

Tropical Luxury Dreams

house, Ocho Rios
Ideally located in Ocho Rios, this villa is a mere 17-minute walk from Sunset Beach and a 19-minute walk from Mahogany Beach, with Ocho Rios Bay Beach also just 1.3 kilometres away.
This well-appointed holiday home offers 2 bedrooms, a living room, an equipped kitchen, and 2 bathrooms, accommodating up to 13 guests, and boasts a balcony with mountain views, access to a swimming pool, a garden, and wellness packages.
Aqua Vista- Luxury Waterfront Pool Home, 35' Dock! - Caribbean
No reviews

Aqua Vista- Luxury Waterfront Pool Home, 35' Dock!

house, Key Colony Beach
This luxurious waterfront villa in Key Colony Beach boasts a private 35-foot dock and direct beach access, just a 5-minute walk from Sunset Park Beach and 2.2 kilometres from Florida Keys Aquarium Encounters.
Offering 234 square metres of living space, this spacious holiday home accommodates up to 15 guests across 4 bedrooms and 4 bathrooms, featuring a year-round outdoor pool, air conditioning, and a fully equipped kitchen.
Luxury Oceanfront Villa With Heated Pool, Jacuzzi, Ac, Bbq, Starlink Wi-fi, Chef's Kitchen, Staff Included, Mountain Views, Near El Quemaito, San Rafael, And Los Patos Beach - Caribbean
8.0 1 review

Luxury Oceanfront Villa With Heated Pool, Jacuzzi, Ac, Bbq, Starlink Wi-fi, Chef's Kitchen, Staff Included, Mountain Views, Near El Quemaito, San Rafael, And Los Patos Beach

house, Santa Cruz de Barahona
Directly on the oceanfront in Santa Cruz de Barahona, this luxury villa is just 1.9 kilometres from Bahoruco Beach and close to El Quemaito, San Rafael, and Los Patos Beach.
This expansive holiday home boasts 1500 square metres of floor area, accommodates up to 23 guests across 4 bedrooms and 6 bathrooms, and features a heated infinity pool, Jacuzzi, a chef's kitchen, and Starlink Wi-Fi.

Villas and family holiday home rentals in the Caribbean

Where to find family villa rentals in the Caribbean for the whole group? Spacious layouts and shared living areas feature among many family holiday homes.

85 M² House ∙ 2 Bedrooms ∙ 4 Guests - Caribbean
9.3 15 reviews

85 M² House ∙ 2 Bedrooms ∙ 4 Guests

house
Located within a secure gated community, this villa offers convenient access, being just a 5-minute drive from Falmouth Town Centre and the beach, and approximately 40 kilometers from Sangster International Airport.
This welcoming holiday home, spanning 85 square meters, accommodates up to four guests with two bedrooms and one bathroom, featuring a fully-equipped kitchen, air conditioning, and a private garden with outdoor furniture for al fresco relaxation.
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
Holiday house to rent. Your accommodation will be located in Key Largo.
Services and facilities include free parking, a terrace and a washing machine. This house in Key Largo also has a Jacuzzi to relax in!
New The Windrose House - Pool & Pets - Caribbean
No reviews

New The Windrose House - Pool & Pets

house, Key West
House. You will be located in Key West.
Facilities and services include a swimming pool, a barbecue and free parking. Take advantage of the terrace in this house in Key West.
Cozy Cottage Near Vanderbilt Beach - Caribbean
9.6 25 reviews

Cozy Cottage Near Vanderbilt Beach

cottage, Naples Park
Located in Naples Park, this welcoming cottage is just a short walk from Mercato's dining and shopping, and 1.5 kilometres from Vanderbilt Beach, offering excellent access to local amenities.
This family-friendly holiday home boasts three bedrooms, two bathrooms, and a capacity for eight guests, featuring a well-equipped kitchen, air conditioning, and a large, fenced garden with a terrace and barbecue for outdoor enjoyment.

Rental villas and holiday homes with jacuzzi in the Caribbean

The finest villa rentals with hot tub in the Caribbean offer private terraces and outdoor jacuzzis. Find your holiday home with hot tub.

The Butterfly Cottage - Certified Butterfly Sanctuary - Ocean View Hot Tub - Authentic Keys Charm - Caribbean
9.0 25 reviews

The Butterfly Cottage - Certified Butterfly Sanctuary - Ocean View Hot Tub - Authentic Keys Charm

house, Marathon
Entire Private Beautiful 2 Bedroom Plus Den House With Gated Front&back Yard And Free Parking 10min Drive To Miami Beach - Caribbean
9.4 264 reviews

Entire Private Beautiful 2 Bedroom Plus Den House With Gated Front&back Yard And Free Parking 10min Drive To Miami Beach

house, Miami
190 M² Villa ∙ 3 Bedrooms ∙ 6 Guests - Caribbean
8.0 1 review

190 M² Villa ∙ 3 Bedrooms ∙ 6 Guests

house, Sosúa
Lely Resort Home W/ Lanai - 1 Mi To Golf Course! - Caribbean
9.2 27 reviews

Lely Resort Home W/ Lanai - 1 Mi To Golf Course!

house, Lely Resort
copyright © 2026 villapicker.com