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Holiday rentals with a pool in Trelawny

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Trelawny

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Superhost
A private pool area is showcased, featuring a sparkling blue pool bordered by a stone deck. Lounge chairs in vibrant orange are positioned for relaxation, with a grass-like surface nearby. A decorative wall displays the Villa Di-Nae name, enhancing the overall inviting atmosphere.
Home in Falmouth
4.81 out of 5 average rating, 53 reviews

Villa Di-Nae, The luxury getaway

Nestled in Falmouth, Jamaica, Villa Di-Nae is a true gem that embodies the essence of authentic Jamaican culture, 10 mins away from Martha brae river rafting and 25 mins from MBJ airport. We offer a sparkling pool that beckons guests to take a refreshing dip. The villa boasts an exceptional private chef extra cost dedicated to crafting authentic Jamaican cuisine. Guests are treated to indulge in traditional dishes bursting with flavors Each meal is a celebration of Jamaica's culinary heritage

Guest favourite
A spacious living area features a large sectional sofa in soft gray, accented with colorful throw pillows. A round coffee table sits in the center, surrounded by an area rug. Bright orange curtains frame the windows, enhancing the light that fills the room. A dining area is visible in the background.
Home in Falmouth
4.79 out of 5 average rating, 100 reviews

OceanView Villa 2BR | PoolslTennis|Gym, StoneBrook

Enjoy fascinating views of the scenic landscape of Falmouth, Trelwany with the breathe taking shoreline in the horizon from an amazingly furnished 2 - bedroom villa in a brand new, luxury, gated community. Our villa provides the perfect comfort for that couples getaway, friends excursion and family vacation. Located just 5 - 10 minutes drive from the historic town of Falmouth with major attractions such as Rafting on the Martha Brae river, Glistening water Lagoon tours and white sand beaches.

Guest favourite
A black bench offers a comfortable seating area overlooking a scenic view of the Caribbean Sea. The expansive stone wall frames the lush green landscape, while the distant horizon features a clear blue sky. The peaceful outdoor setting invites relaxation.
Home in Falmouth
4.89 out of 5 average rating, 66 reviews

Serene 180° Valley Ocean View! Solar Powered Home!

Experience the epitome of Caribbean luxury at Serene 180° Valley Ocean View! Perched atop a hill with a breeze, this villa offers breathtaking views of the Caribbean Sea within a 24hrs gated secured community, making it the perfect retreat for relaxation and exploration. With resort-style amenities and proximity to popular attractions, it's an ideal base for your Jamaican adventure. Book now for an unforgettable stay! To maintain a pristine environment, smoking is strictly prohibited indoors.

Guest favourite
Home in Coral Spring
5 out of 5 average rating, 15 reviews

Luxury 3BR Villa | Pool | 30 min from MBJ Airport!

Welcome to Coral House Villa—a serene, spacious, and beautifully renovated three-bedroom retreat nestled in Coral Spring, Trelawny. Designed for comfort and infused with authentic island charm, this is the perfect place to relax and feel at home. Just minutes from the beach and Luminous Lagoon, Coral House Villa offers the ideal balance of peace and relaxation. Whether you’re traveling with family or friends, this bright and breezy oasis has everything you need for a truly memorable stay.🌴

Superhost
Home in Falmouth
4.76 out of 5 average rating, 17 reviews

Modern Serenity Rest | Falmouth & Near Montego Bay

Trelawny Private Modern 2BR – Gated | Pool & Tennis Court Access | Car & Driver Optional. 30 mins from Montego Bay Airport and 5 mins to beaches, shopping malls, and restaurants. Unwind in this modern, fully air-conditioned home located in a secure gated community with 24-hour security. Enjoy pool access, stylish comforts, and peaceful surroundings—perfect for a family or couple. Car rental, driver & airport pickup available on request. Serenity, conveniences, and island charm await you!

Top Guest favourite
A single-story building with a green exterior is surrounded by a well-maintained lawn and flower beds. A driveway leads to the entrance, flanked by decorative planters. The nearby area features similar houses under a clear blue sky, with distant views of the ocean.
Home in Falmouth
4.88 out of 5 average rating, 102 reviews

Getaway Home

Escapada a Casa (Getaway home) is centrally located in beautiful Stonebrook Manor, Falmouth, Jamaica, in a quiet and safe gated community with 24 hour security. In close proximity to restaurants, popular local entertainment, beaches and attractions such as: Blue Water Beach Club; Hampden Estate; Jamaica Swamp Safari Village; Historic Falmouth Cruise Port; Burwood Beach; Rafting on the Martha Brae River; Good Hope Plantation etc. All are welcome to experience this wonderful accommodation.

Guest favourite
A spacious swimming pool is surrounded by lush landscaping, featuring comfortable lounge chairs along the water's edge. The pool is complemented by a well-appointed building with multiple windows and a welcoming entryway. Additional amenities are visible, enhancing the outdoor leisure experience.
Holiday home in Stonebrook Manor
4.9 out of 5 average rating, 20 reviews

Tropical Escape: Spacious 2-Bedroom Vacation Oasis

Bring the whole family to Stonebrook Manor just 25 minutes from Montego Bay Airport! Explore nearby attractions like Martha Brae Rafting Village, Luminous Lagoon, Falmouth Swamp Safari, Blue Water Beach Club, and Rio Bueno Tubing Safari. Iconic spots like Doctor’s Cave Beach, Margaritaville, Green Grotto Caves, Dunn’s River Falls, and Blue Hole are within reach. Located in a gated community with free parking, my home is the perfect tropical retreat. Relax, unwind, and create memories!

Top Guest favourite
A modern living area is presented with a large sectional sofa adorned with decorative pillows. A marble-topped coffee table occupies the center, with a vase of sunflowers adding a cheerful touch. The room is illuminated by soft natural light filtered through elegant wooden blinds.
Home in Falmouth
4.98 out of 5 average rating, 110 reviews

Villa Renee'

This modern eco friendly house is your perfect getaway space offering comfort, 24 hrs security and tranquility. The property is in close proximity to the highway which makes it the ultimate vacation location/home. All the best attractions on the islands north coast are minutes away (Glistening Waters, Green Grotto Caves, 876 Beach, Burwood Beach, Pueto Seco beach, Dunn's River fall's, Dolphin Cove, Chukka Adventure Park and many more). Perfect for family, friends or work travel.

Guest favourite
A spacious outdoor area features a swimming pool surrounded by lounge chairs and a covered seating area. Vibrant blue chairs are positioned near the pool, while lush greenery provides a natural backdrop, enhancing the serene environment.
Villa in Duncans
4.93 out of 5 average rating, 86 reviews

Adehya the Villa

Adehya, a Jamaican phrase for "I've arrived" is the quintessential vacation spot in Jamaica. Located in the gated community of Silver Sands Estate, Trelawny, you will have access to the estate's facilities and beaches nearby. Also included in your vacation package is a staff consisting of a housekeeper, butler and a chef. Feeling adventurous? No worries. We can arrange or suggest a list of activities and attractions for you to visit. Adehya is your home away from home.

Guest favourite
A vibrant pool area is depicted, featuring several people enjoying the water. Splashes are captured mid-action, highlighting a lively atmosphere. Lounge chairs are positioned in the background, while greenery outlines the space, enhancing the outdoor experience.
Villa in Stonebrook Manor
4.94 out of 5 average rating, 104 reviews

Jhadano*3BR*Oceanview*Pool*Shuttle-Gym*Gated

🌴✨ Luxurious Retreat in Paradise! 🌴✨ The whole group will love this centrally located ocean view getaway in upscale gated community. Spacious, stylish, clean and fully equipped with modern amenities. Leave all your worries at home and unwind Jamaican style enjoying our warm sunshine. We offer free airport shuttle (up to 2 guests, 2 nt. min). We even offer transportation to attractions and meal plans. Nothing to do but pack and show up. We look forward to your escape✨

Superhost
A large swimming pool is surrounded by well-maintained greenery and palm trees. Bright blue water reflects the clear sky, while lounge chairs are positioned around the pool area for relaxation. A signboard can be seen in the background, indicating pool rules and information.
Home in Falmouth
4.9 out of 5 average rating, 51 reviews

Kl Hidden Gem-Ocean view

Bring the whole family to this great place with lots of room for fun. Located 35 minutes from the Montego Bay Airport and 40 minutes away from Ocho Rios, this relaxing retreat will make you feel right at home. We offer 24-hr security along with security cameras on the premises. A swimming pool, gym and jogging trail are some of the amenities offered. All located within 8 minutes is the 876 Beach, Margaritaville, Rafting at Martha Brae and the Falmouth Cruise Pier.

Superhost
The living area features a spacious layout with comfortable gray sofas, accented by gold cushions. A large flat-screen TV is mounted on the wall, while a round coffee table sits centrally. Sunlight streams through the windows, illuminating the tiled floor.
Home in Florence Hall Village
4.82 out of 5 average rating, 120 reviews

Oasis at the Manor w/ King Bed, shared pool & gym

Step into a beautiful 2-bed/2-bath home adorned with modern transitional decor, crafting the ultimate sanctuary for rejuvenation and tranquility. Indulge in this modern oasis boasting black stainless-steel appliances, smart TVs, a serene front door patio, and a cozy backyard gazebo. Enjoy countless scenic views within a secure, gated community with 24-hour security. Community perks include a pool, gym, clubhouse, and scenic walking trail.

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