Search cheap cottages in Caribbean from 100+ sites!

3574 available cottage rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Caribbean cottages
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

3574 Best cottages in Caribbean

Best family friendly Caribbean cottages

Among the 3574 accommodations in Caribbean, here are the 4 best family friendly cottages

St.john, Virgin Islands!  2 Bedroom, 1.5 Bath, Beautiful Tropical Gardens! - Caribbean
9.8 23 reviews

St.john, Virgin Islands! 2 Bedroom, 1.5 Bath, Beautiful Tropical Gardens!

cottage, St. John
This St. John vacation home is conveniently located near Virgin Islands National Park (0.6 miles) and Trunk Bay (2.9 miles), with Hawksnest Bay and Battery beaches also within a short drive.
The two-bedroom, two-bathroom rental sleeps five, offering a fully equipped kitchen, air conditioning, Wi-Fi, a terrace, and a private garden with barbecue grills, perfect for exploring St. John's natural beauty and nearby beaches.
Water At Your Back Door - Caribbean
8.8 34 reviews

Water At Your Back Door

cottage, Cudjoe Key
This waterfront vacation rental is conveniently located near Venture Key, Venture Out Keys, and Out Key, and is within 6 miles of Upper Sugarloaf Key and Florida Keys Beaches. It has received very good ratings from previous guests. The two-bedroom cottage can comfortably accommodate up to six guests. The home features a private pool, a hot tub, a tennis court, and a barbecue grill for your enjoyment.
Sunrise Cottage - Caribbean
10 2 reviews

Sunrise Cottage

cottage, Savannah Sound
Sunrise Cottage, a one-bedroom house in Savannah Sound, Eleuthera, is minutes from Ten Bay Beach, a top-ten Eleuthera beach, and a short drive from Rock Sound Airport.
This pet-friendly vacation rental sleeps three, boasts a fully equipped kitchen, two Ultra HD smart TVs, a large deck with ocean views, and includes mid-week housekeeping for stays of six days or more.
The Historic Coquina Cottages C Is 2 Blocks To The Beach, 5th Avenue And 3rd St. - Caribbean
10 21 reviews

The Historic Coquina Cottages C Is 2 Blocks To The Beach, 5th Avenue And 3rd St.

cottage, Naples
This Old Naples cottage is located steps from Naples Beach, Naples Pier, and Third Street South, within a 10-minute walk of Fifth Avenue South and the Historic Palm Cottage.
This 300-square-foot, one-bedroom, one-bathroom house sleeps two guests and features a fully equipped kitchen, free WiFi, a patio, a garden with barbecue grills, and is a short walk from many attractions.

Best Caribbean cottages with a garden

2 Bedroom 1,079 Sf Cottage. Dock. Full Kitchen, Wi-fi,hdtv, Parking & Pets Ok. - Caribbean
10 47 reviews

2 Bedroom 1,079 Sf Cottage. Dock. Full Kitchen, Wi-fi,hdtv, Parking & Pets Ok.

cottage, Stuart
This waterfront cottage is nestled in the quiet Snug Harbor area of Stuart, Florida, a short drive or bike ride from Historic Downtown Stuart and Hutchinson Island's beaches. The cottage has excellent user ratings and provides a unique and appealing experience for guests.
The cottage has a spacious living area of 1,079 square feet with two generous bedrooms, a Florida room, and a separate dining area. It features modern amenities such as three wall-mounted flat-screen HDTVs, Wi-Fi, and full laundry facilities. Guests can also enjoy a private dock, a Weber BBQ, and a fully enclosed rear yard.
Beach Days & Backyard Nights! Fort Myers Retreat - Caribbean
No reviews

Beach Days & Backyard Nights! Fort Myers Retreat

cottage, Harlem Heights
This cottage is located in the Harlem Heights district, offering easy access to HealthPark Hospital, FastTrax Fort Myers, and Smugglers Cove Adventure Golf, all within 5 miles, and within 10 miles of Key West Express and Estero Bay Preserve State Park.
This rental property allows pets and features air conditioning, a microwave oven, a garden, and parking, with complimentary Wi-Fi available in common areas and barbecue facilities for guest use.
Coastal Caribbean Cottage - Caribbean
No reviews

Coastal Caribbean Cottage

cottage, St Thomas
This Northside St. Thomas cottage, a surfer's destination, offers ocean views and is located within a 5 to 15-minute drive of Hull Bay beach, The Shack, FishBar, and Magen's Bay.
This one-bedroom, two-bathroom rental accommodates two guests and features air conditioning, internet, a garden, parking, a backup generator, and potable tap water, with ocean views from two balconies.
Palmetto Cottage On The Beach With Perfect Views. - Caribbean
10 38 reviews

Palmetto Cottage On The Beach With Perfect Views.

cottage, Spanish Wells
This Spanish Wells beach house offers direct beach access and is located 0.1 km from the Lucayan Archipelago and within 15.5 miles of Pink Sands Beach and the Government Dock.
This three-bedroom, three-bathroom vacation rental sleeps six, features a fully equipped kitchen with a fridge, microwave, and dishwasher, a private balcony, free WiFi, a garden, on-site playground, barbecue grills, and ample parking.

Frequently Asked Questions about cottages in Caribbean

  • What are the top must-see attractions in the Caribbean?

    The Caribbean is vast! Top attractions depend on the island, but some highlights include: Old San Juan in Puerto Rico, with its colorful colonial architecture and forts like Castillo San Felipe del Morro; the pristine beaches of Barbados, like Crane Beach; Dunn's River Falls in Jamaica, perfect for climbing; and the breathtaking underwater scenery of the coral reefs around Grand Cayman, ideal for snorkeling or diving. Each island offers unique experiences.
  • What are the best cottages in Caribbean?

  • How to spend a 5-day holiday in the Caribbean?

    A 5-day trip needs focus. Pick an island! For relaxation, spend your days on the beach, maybe trying watersports like paddleboarding or kayaking. For adventure, explore rainforests like El Yunque National Forest in Puerto Rico or hike to waterfalls. Consider a mix: beach days paired with exploring a historical city like Havana, Cuba, or Port-au-Prince, Haiti. Remember to factor in travel time between islands if you plan to island hop.
  • What are the best cottages with a pool in Caribbean?

  • Is the Caribbean a good destination to rent a cottage?

    Absolutely! Many Caribbean islands offer charming cottages for rent, particularly in areas like the countryside of Jamaica or the quieter parts of islands like St. Lucia. These offer a more authentic and intimate experience than large resorts. Look for rentals through reputable websites or local agencies, and check reviews carefully.
  • What are the best cottages with a jacuzzi in Caribbean?

  • What weather, wildlife, or natural hazards might affect travelers in the Caribbean?

    Hurricane season (June 1st to November 30th) is a major consideration. Check forecasts before you go. Mosquitoes are prevalent, so pack repellent. Some islands have venomous snakes or spiders, though encounters are rare. Be aware of strong sun and stay hydrated. Rip currents can be dangerous on beaches; always heed lifeguard warnings.
  • What are the best cottages for families and kids in Caribbean?

  • Is the Caribbean pedestrian and cyclist-friendly?

    It varies greatly by island and location. Some areas, especially tourist hubs, are well-suited for walking, while others are more car-dependent. Cycling is more challenging in many areas due to hilly terrain and limited dedicated bike lanes. Public transportation is available on most islands, but its reliability can be inconsistent.
  • What are the best pet friendly cottages in Caribbean?

  • Are there any unusual or hidden places to explore in the Caribbean?

    Yes! Explore the lesser-known islands like Dominica, known for its lush rainforests and natural hot springs, or explore the secluded beaches of Vieques, Puerto Rico. Seek out local guides for hidden waterfalls or caves. Many islands have unique historical sites or archaeological ruins off the beaten path.
  • What are the best cottages with parking in Caribbean?

  • What are some of the best cultural experiences that allow you to meet locals in the Caribbean?

    Attend local festivals like Carnival in Trinidad and Tobago or Crop Over in Barbados. Visit local markets, like the Mercado Central in San Juan, Puerto Rico, to interact with vendors and experience the local life. Take a cooking class to learn traditional recipes and interact with chefs. Consider staying in a guesthouse or a locally-owned hotel for a more immersive experience.
  • What are the best authentic dishes to taste in the Caribbean?

    It depends on the island! Jerk chicken in Jamaica is iconic. Try mofongo (mashed plantains) in Puerto Rico. Conch fritters are common in the Bahamas. Roti is a staple in Trinidad and Tobago. Many islands have their unique variations on rice and beans. Explore local restaurants and street food stalls for the best authentic flavors.
  • Are there any recommended items to pack for a stay in the Caribbean?

    Pack light clothing, swimwear, sunscreen (high SPF!), insect repellent, a hat, sunglasses, and comfortable walking shoes. A reusable water bottle is essential. If you plan on hiking or watersports, pack appropriate gear. Consider a light rain jacket, as showers can be brief but intense. Don't forget any necessary medications.

Best Caribbean cottages with jacuzzi

Among the 3574 accommodations in Caribbean, here are the 4 best cottages with a jacuzzi

Heated Pool / Las Olas / Victoria Park / Near Beach / Escapism At Its Finest / Mermaid Key - Caribbean
10 3 reviews

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

cottage, Fort Lauderdale
This pet-friendly cottage is located in East Fort Lauderdale, a short walk from Las Olas Boulevard and 0.6 miles from the Riverwalk.
This 3-bedroom, 3-bathroom house accommodates up to 10 guests and features a full kitchen, air conditioning, a swimming pool, hot tub, and garden, with concierge and parking available.
Luxury Cottage, 1bd/1ba Steps To Pool+7 Mile Beach - Caribbean
No reviews

Luxury Cottage, 1bd/1ba Steps To Pool+7 Mile Beach

cottage, Grand Cayman
This Grand Cayman beachfront cottage boasts direct access to Seven Mile Beach, near Governors Square and The Strand Shopping Center.
The 600-square-foot one-bedroom, one-bathroom unit sleeps four, featuring a full kitchen, Jacuzzi, and complimentary beach chairs and umbrellas; a mid-stay refresh option is available for longer stays.
Island Cottage In Jensen Beach W/ Pool Access! - Caribbean
No reviews

Island Cottage In Jensen Beach W/ Pool Access!

cottage, Jensen Beach
This Jensen Beach vacation home is located in Hutchinson Island South, within three miles of Waveland Beach, Fort Pierce Beach, and Normandy Beach, and six miles from Herman's Bay Beach and Ocean Bay Beachside.
This 720-square-foot, two-bedroom, two-bathroom cottage sleeps four and features a fully equipped kitchen, in-unit laundry, a private swimming pool, Jacuzzi, and access to an on-site fitness center and tennis court.
Ecoscape Tulia - Private Nature Escape -  1 Bedroom, 30 Minutes To Ocho Rios - Caribbean
No reviews

Ecoscape Tulia - Private Nature Escape - 1 Bedroom, 30 Minutes To Ocho Rios

cottage, St. Ann Parish
Ecoscape Tulia, a riverside cottage rental in New Ground, Limehall, St. Ann Parish, Jamaica, is a 12-minute drive from the Draxhall Knutsford Express stop and offers easy access to Dunn's River Falls and Mystic Mountain.
This one-bedroom, one-bathroom cabin sleeps two guests and features a king-size bed, full kitchen (fridge, microwave), air conditioning, private deck, and an adventure package including river swimming and grilling, all within a lush, secluded setting with a private spring.

Best pet friendly Caribbean cottages

Among the 3574 accommodations in Caribbean, here are the 4 best pet friendly cottages

Jupiter Kozy Kottage- New July Open,2.7 From Ocean - Caribbean
10 362 reviews

Jupiter Kozy Kottage- New July Open,2.7 From Ocean

house, Jupiter
This charming cottage is located in Jupiter, just a short distance from the beach and close to the Boca Grande Bike Trail, Health Promoters, and Jupiter Medical Center. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The cottage features one bedroom and one bathroom, providing space for two guests. Enjoy the amenities, including a fully equipped kitchen, a private fenced yard, a patio, a jacuzzi, and a garden, perfect for relaxing and enjoying the beautiful Jupiter weather.
Sands Of Time Is Ready For You - Caribbean
9.6 15 reviews

Sands Of Time Is Ready For You

cottage, Rainbow Bay
This pet-friendly Rainbow Bay cottage, a new build, is conveniently located near James Cistern Dock and Government Dock, offering easy access to Briland's Blue Hole and OceanView Farm (distances to attractions require further clarification).
The 1180-square-foot (approximately 109 square meter) vacation home features three queen bedrooms, two bathrooms, and a spacious open-concept living, dining, and kitchen area with a refrigerator and microwave, accommodating up to six guests and including air conditioning, a garden, and parking.
Marina View Cottage At Key Largo - Caribbean
9.8 10 reviews

Marina View Cottage At Key Largo

cottage, Key Largo
This waterfront cottage in Key Largo offers direct marina views and water access, situated just 2 minutes from TJ Maxx, Burlington, and Publix.
This 2-bedroom, 1-bathroom house accommodates up to 6 guests and features a full kitchen, air conditioning, a swimming pool, jacuzzi, garden, parking, and an outdoor kitchen, with proximity to John Pennekamp Coral Reef State Park and Dagny Johnson Key Largo Hammock Botanical State Park.
Colony Sunset- Bright And Airy Cottage In The Heart Of Old Town Key West - Caribbean
9.8 118 reviews

Colony Sunset- Bright And Airy Cottage In The Heart Of Old Town Key West

cottage, Key West
This charming Key West cottage is located in The Colony, a gated community just steps from Duval Street, offering a peaceful retreat while still being close to the action. Guests rave about the cottage's excellent rating, highlighting its comfortable and relaxing atmosphere.
The cottage offers 530 square feet of living space, featuring one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy a private deck, a shared pool, and a fully equipped kitchen with a sit-down bar, perfect for enjoying meals and relaxing after a day of exploring Key West.
©2026 cozycozy.com