Best Vacation Homes in Caribbean Islands
Villa
10.0(182 Reviews)
6 Bedrooms
7 Baths
18 Guests
4000 ft²
Private Pool
Oceanfront
Pool
Ocean View
£300/Night
7 Nights - £2,101
Ski Chalet
10.0(17 Reviews)
1 Bedroom
1 Bath
3 Guests
452.08 ft²
Hot Tub- Ocean View
Balcony/Terrace
View
£23/Night
7 Nights - £160
Apartment
10.0(35 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Pool
- Ocean View
£43/Night
7 Nights - £304
Villa
10.0(179 Reviews)
5 Bedrooms
3 Baths
14 Guests
8100 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£810/Night
7 Nights - £5,673
Apartment
10.0(16 Reviews)
3 Bedrooms
2 Baths
6 Guests
1184.03 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£88/Night
7 Nights - £614
House
10.0(175 Reviews)
6 Bedrooms
7 Baths
12 Guests
12917 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£1,904/Night
7 Nights - £13,331
Villa
10.0(139 Reviews)
5 Bedrooms
4 Baths
12 Guests
6600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£582/Night
7 Nights - £4,074
Villa
10.0(124 Reviews)
4 Bedrooms
2 Baths
10 Guests
5000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£1,205/Night
7 Nights - £8,432
Caribbean Islands Luxury Rentals
Villa
12 Bedrooms
12 Baths
25 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
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New
Villa
10 Bedrooms
10 Baths
24 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
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Villa
1 Bedroom
10 Baths
16 Guests
5005.22 ft²
- Private Pool
- Pool
Parking
Air Conditioner
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Villa
10 Bedrooms
11 Baths
24 Guests
37600 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
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Villa
9 Bedrooms
10 Baths
18 Guests
- Private Pool
- Hot Tub
Fireplace/Heating- Pool
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Villa
10.0(1 Review)
12 Bedrooms
12 Baths
24 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
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New
Villa
6 Bedrooms
6 Baths
18 Guests
- Oceanfront
- Pool
- Ocean View
- View
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Villa
20 Bedrooms
17 Baths
40 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
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Caribbean Islands Pet Friendly Vacation Rentals
Villa
10.0(93 Reviews)
14 Bedrooms
16 Baths
36 Guests
12000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£1,596/Night
7 Nights - £11,175
House
10.0(16 Reviews)
3 Bedrooms
2 Baths
9 Guests
96.88 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
£85/Night
7 Nights - £593
Cabin
10.0(4 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
£89/Night
7 Nights - £625
Villa
10.0(91 Reviews)
3 Bedrooms
3 Baths
12 Guests
4306 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£301/Night
7 Nights - £2,109
Villa
10.0(15 Reviews)
2 Bedrooms
2 Baths
7 Guests
914.93 ft²
Private Beach- Oceanfront
- Hot Tub
- Pool
£88/Night
7 Nights - £614
Villa
10.0(73 Reviews)
13 Bedrooms
16 Baths
28 Guests
21528 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
£2,308/Night
7 Nights - £16,157
Villa
10.0(67 Reviews)
6 Bedrooms
7 Baths
14 Guests
10764 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
£1,252/Night
7 Nights - £8,766
House
10.0(60 Reviews)
12 Bedrooms
11 Baths
24 Guests
24000 ft²
- Private Pool
- Hot Tub
Spa- Pool
£6,385/Night
7 Nights - £44,694
Caribbean Islands Large Vacation Homes
Villa
10.0(119 Reviews)
5 Bedrooms
5 Baths
14 Guests
6489 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£659/Night
7 Nights - £4,615
Bed & Breakfast
10.0(15 Reviews)
6 Bedrooms
4 Baths
14 Guests
247.57 ft²
Breakfast
Pet Friendly
Kitchen- Parking
£16/Night
7 Nights - £113
Villa
10.0(5 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Parking
- Air Conditioner
£177/Night
7 Nights - £1,242
Villa
10.0(107 Reviews)
5 Bedrooms
4 Baths
12 Guests
6000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,053/Night
7 Nights - £7,374
Villa
10.0(14 Reviews)
2 Bedrooms
2 Baths
8 Guests
1291.67 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Pool
£463/Night
7 Nights - £3,239
Villa
10.0(101 Reviews)
4 Bedrooms
4 Baths
10 Guests
7481 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£779/Night
7 Nights - £5,456
Villa
10.0(100 Reviews)
5 Bedrooms
5 Baths
12 Guests
8070 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,063/Night
7 Nights - £7,441
Villa
10.0(96 Reviews)
5 Bedrooms
6 Baths
12 Guests
6000 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
£591/Night
7 Nights - £4,140
Why Choose Rent By Owner for your Caribbean Islands Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Caribbean Islands
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination ensures you enjoy its best weather and vibrant atmosphere, making your Caribbean Islands vacation rentals an unforgettable experience.
Peak Season Highlights
December to April
During these months, you'll experience the most favorable weather with warm days and minimal rainfall, perfect for exploring the area’s beaches and outdoor activities.
Average Temperature Daytime: 78°F to 85°F - Nighttime: 70°F to 75°F
July to August
This summer period offers vibrant atmosphere and lively events, making it an ideal time for those seeking a bustling Caribbean experience.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 76°F to 80°F
Off-Season Highlights
May to June
In this shoulder season, you can enjoy fewer crowds and more affordable rates while still experiencing warm weather and pleasant conditions.
Average Temperature Daytime: 82°F to 87°F - Nighttime: 72°F to 77°F
September to November
This period sees less tourist activity due to the wetter season, but it's a great opportunity to find special deals on vacation rentals before the peak months return.
Average Temperature Daytime: 80°F to 85°F - Nighttime: 73°F to 77°F
Weekly Weather Forecast for Caribbean Islands
How to Book Your Caribbean Islands Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Caribbean Islands
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor swimming pool to relax and unwind in the warm Caribbean sun.
- Benefit from lush, tropical landscaping that enhances your outdoor living experience.
- Take advantage of spacious patios or verandas perfect for outdoor dining or lounging.
- Celebrate the sunset with a cozy outdoor seating area designed for gatherings.
- Make use of well-maintained gardens that add natural beauty around your accommodation.
- Stay active with access to outdoor sports amenities such as volleyball courts or tennis courts.
- Relax on a hammock amidst the scenic surroundings to enjoy the tranquil island environment.
Top Attractions Around Caribbean Islands
What attractions are nearby?
Here, you can immerse yourself in a variety of exciting outdoor activities and cultural experiences that showcase the vibrant spirit of this destination, making your stay truly memorable.
Family Activities
- Snorkeling Adventures: Explore the vibrant coral reefs and marine life in the clear waters surrounding your Caribbean Islands vacation rentals, providing an exciting activity for the whole family.
- Beach Day Activities: Relax on the pristine beaches of this destination, building sandcastles, swimming, or enjoying a leisurely picnic with your loved ones.
- Water Sports Excursions: Engage in kayaking, paddleboarding, or windsurfing, offering fun-filled experiences right from the doorstep of your Caribbean Islands stay.
- Cultural Tours and Festivals: Discover local traditions and history through family-friendly tours and lively festivals that highlight the area's rich cultural heritage.
Adult Activities
- Snorkeling and Scuba Diving: Explore vibrant coral reefs and marine life in the clear waters, making your stay here an underwater adventure.
- Island Hopping Tours: Discover nearby islands and secluded beaches, offering a perfect blend of relaxation and exploration in this tropical region.
- Water Sports Activities: Engage in activities like paddleboarding, jet skiing, and windsurfing to enjoy the warm ocean waters and sunny skies.
- Spa and Wellness Treatments: Unwind with luxurious spa services that harness the region's natural ingredients, promoting relaxation amidst stunning seaside settings.
Other Places to Stay in Caribbean Islands
Dominican Republic
Hispaniola
Punta Cana
East Coast
North Coast
Puerto Plata
Puerto Plata
La Altagracia
Santo Domingo
Bavaro
Distrito Nacional
Caribbean Islands Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Experiences: Research unique cultural events and outdoor activities to immerse yourself in the authentic vibe of the region during your stay.
- Choose the Right Accommodation: Opt for a centrally located vacation rental that offers easy access to the area's beaches, dining, and attractions for a hassle-free experience.
- Respect the Environment: Practice eco-friendly habits, such as reducing waste and conserving water, to help preserve the natural beauty that draws visitors here.
- Stay Connected with Local Tips: Engage with hosts or locals to get insider advice on the best hidden spots and activities tailored to your interests in this destination.
Transportation Options
- Commercial Airports: Major airports in the region offer convenient flights, making it easy for you to access popular Caribbean Islands directly from numerous international destinations.
- Ferries and Water Taxis: These boat services connect islands and coastal areas, providing scenic and efficient transportation options for exploring the nearby regions within the Caribbean.
- Car Rentals: Renting a vehicle on the island gives you flexibility and independence to explore at your own pace, ideal for discovering hidden gems and local attractions.
- Public Buses and Local Transport: Budget-friendly buses and shared transportation systems are readily available, offering an authentic way to experience the area's culture and daily life.
Local Customs Options
- Dance and Music Traditions: You will notice that lively dance styles and regional music like calypso and reggae are integral to the area's cultural celebrations, reflecting the vibrant spirit of the islands.
- Local Festivals: Participating in regional festivals allows you to experience authentic customs, where traditional foods, costumes, and performances showcase the unique heritage of the destination.
- Greetings and Social Etiquette: Respectful greetings such as handshakes or cheek kisses are common here, and observing local manners will help you connect more genuinely with residents.
- Cuisine and Food Customs: Sampling local dishes often involves sharing meals in communal settings, emphasizing the importance of hospitality and familial bonds cherished in this region.
Frequently Asked Questions About Caribbean Islands?
1. What are the top vacation rentals in Caribbean Islands?
There are a lot of options in Caribbean Islands. If you plan on staying in the Caribbean Islands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Caribbean Islands:
- Affordable Luxury at 6 BR Fully Staffed Caribbean Vacation Villa
- KID-FRIENDLY LUXURY VILLA - 300 YARDS FROM BEACH - MAID & CHEF INCLUDED !
- Oceanfront, On Golf Course, Next to Beach, heated pool & hot tub, fully staffed
- Luxury Villa less than 400 meter walk to the Beach - Pool & Jacuzzi Sleeps 10-12
- Casa De Campo All Inclusive ~VIP~ Package Chef & Butler
- 120 +5 STAR reviews below 3 Min to Beach English speaking Chef Butler Meal Plan
- Luxury Sunshine Villa -outdoor movie screen & pool heated(50x17ft), CHEF & staff
- ATTRACTIVE RATES JUST REMODELED - Near Beach 4 BD Amazing Golf View Villa
- Luxury Sunshine II. villa with SEA & GOLF VIEW, pool heated, CHEF & staff incl.
- On The Beach Luxury Mediterranean Villa . Gated Community Partial or full staff
2. How many vacation rentals have private pools in Caribbean Islands?
There are 5876 vacation rentals with private pools near Caribbean Islands. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Caribbean Islands are best for families?
If you are looking for a family-friendly vacation home in Caribbean Islands, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Caribbean Islands:
4. How many Rentbyowner vacation rentals are available in Caribbean Islands?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 29980 in the Caribbean Islands area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Caribbean Islands.
5. What is the cancellation policy for vacation rentals in this Caribbean destination?
Cancellation policies vary by property, so you should review the specific listing details or contact the owner directly to understand the terms and any applicable fees before confirming your booking.
6. Are there any additional fees I should be aware of when booking a vacation rental in this region?
Additional fees such as cleaning, security deposits, or service charges may apply depending on the property. Always check the listing for detailed fee information or reach out to the owner for clarification.
7. How do I ensure that my booking is secure and reliable?
To guarantee a trustworthy experience, book through listings that are verified and include clear communication options with the property owner. Reading reviews and checking the property's ratings can also help ensure reliability.
8. What amenities are typically included in Caribbean vacation rentals?
Most properties offer essential amenities like Wi-Fi, fully equipped kitchens, and private outdoor spaces. Specific amenities vary, so review each listing carefully to confirm what’s included for your stay.
9. How far in advance should I book my vacation rental to secure the best availability?
It’s advisable to book several months ahead during peak travel seasons to ensure the best selection and availability. Low season bookings can often be made closer to your arrival date, but early planning helps secure your preferred property.
Caribbean Islands Top Rated Vacation Rentals
House
10.0(86 Reviews)
6 Bedrooms
6 Baths
15 Guests
12000 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
£2,181/Night
7 Nights - £15,268
Villa
10.0(83 Reviews)
4 Bedrooms
4 Baths
10 Guests
8073 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£390/Night
7 Nights - £2,733
Condo
10.0(75 Reviews)
1 Bedroom
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£89/Night
7 Nights - £623
Villa
10.0(74 Reviews)
5 Bedrooms
5 Baths
12 Guests
8643 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£967/Night
7 Nights - £6,767
Apartment
10.0(74 Reviews)
2 Bedrooms
3 Baths
6 Guests
1668 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
£190/Night
7 Nights - £1,330
Villa
10.0(68 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
£1,267/Night
7 Nights - £8,870
Villa
10.0(68 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£745/Night
7 Nights - £5,217
Villa
10.0(66 Reviews)
10 Bedrooms
10 Baths
32 Guests
22000 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
£807/Night
7 Nights - £5,651
