Holiday rentals with a pool in Trelawny

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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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Guest favourite

A clear swimming pool with a unique dipping section is surrounded by decorative stonework and vibrant landscaping. Lush palm trees are positioned around the area, and views of the distant coastline and town are visible beyond the pool.

Home in Falmouth

4.97 out of 5 average rating, 38 reviews

Experiences by the Bay (with pool, wifi and gym)

Whether your trip to Jamaica is for business or pleasure, enjoy a memorable experience at this luxurious property. Experiences by the Bay is perfect for the off-the-beaten-path guest who wants to explore this scenic island, the millenial-mom who enjoys DIY-ing her family vacations, or the busy professional who is traveling for work. Nestled in the peaceful town of Falmouth, Stonebrook Manor is a gated community with 24- hour security. This entire house is perfect for your serene getaway plans.

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

4.78 out of 5 average rating, 97 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

4.91 out of 5 average rating, 54 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

A light-filled living area features two comfortable sofas adorned with decorative pillows. A central table with decorative items is positioned on a patterned rug, while large windows with sheer curtains allow natural light to fill the space.

Villa in Florence Hall Village

4.96 out of 5 average rating, 23 reviews

Lynnhood Villa

Keep it simple at this peaceful and centrally-located place. Lynnhood Villa is set in a friendly gated community, with 24/7 security. Take a short stroll to the clubhouse where you can enjoy the beautiful well maintained gardens and gain access to the luxurious pool and the fully equipped gym. The local beach is a 2 minute drive away and the friendly locals will make you comfortable. Montego Bay is the nearest town 30 minutes drive. Go shopping or enjoy a selection of restaurants and bars.

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, 92 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 cozy bedroom is furnished with a spacious bed adorned with a quilt and decorative pillows. Golden curtains frame the window, while light walls contrast with a blue feature wall. A wooden dresser, nightstand, and a decorative tray are visible, enhancing the room's charm.

Bungalow in Falmouth

5 out of 5 average rating, 11 reviews

Kl Hidden Gem Ocean-View II

Bring your spouse or partner for adventure 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.

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, 100 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 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

4.95 out of 5 average rating, 82 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 spacious garden area is visible, featuring a mini pool and a gazebo with outdoor seating. Lush green grass surrounds the space, while distant views of the Caribbean Sea can be seen beyond the fence. Clear blue skies provide a bright backdrop.

Home in Florence Hall Village

4.62 out of 5 average rating, 130 reviews

Jamin Villa (Home w/ prvt pool)

Our private and beautiful villa is located in the gated community of Florence Hall Trelawny, Jamaica. Our rooms are fully air-conditioned, airy and spacious. Wifi available, smart TV in all rooms, wheelchair friendly and ample secured parking available on the property. All amenities for a comfortable and relaxing stay are available. Our villa is equipped with an electronic surveillance system, and adequate security lighten is in place for your comfort and safety.

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

4.85 out of 5 average rating, 108 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.

Superhost

A charming green house is presented with a red tile roof and decorative window bars. Colorful flowers are arranged neatly in front, complementing the landscape. A window air conditioning unit is visible on the side, while a clear blue sky provides a bright backdrop.

Home in Montego Bay

4.76 out of 5 average rating, 34 reviews

Cozy, luxurious two bedroom house.

Forget your worries in this spacious yet cozy, serene space. Located in a safe, gated community with a huge pool and fully equipped gym; perfect amenities to bring your vacation to life! Wake up from your plush king sized bed to a fresh brew of the exotic Jamaican Blue Mountain Coffee ☕️ and remain connected to your favorite platforms with reliable Wifi. Only 10 minutes from the beach 🏝 with views of the sea 🌊 right from the back yard.

Guest favourite

Home in Falmouth

4.89 out of 5 average rating, 55 reviews

2BR Near Falmouth Pier| Beach Access,Pool+Netflix

Great office space with excellent WIFI and solar panels connected, so you'll never lose power. Enjoy a lovely water view to unwind and relax in this calm, stylish space featuring a full kitchen, AC, and smart TVs in each room. Access to two pools in the community. We're just a 30-minute drive from Sangster International Airport (MBJ) in Montego Bay. Your home away from home awaits—come enjoy!