Holiday houses in Stewart Town

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Top-rated holiday rentals in Stewart Town

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

A modern kitchen features sleek cabinetry and stainless-steel appliances. Counter space is organized with utensils and cookware, while a double sink is positioned under a window with horizontal blinds. Decorative towels hang from the stove, adding a touch of warmth to the space.

Home in Discovery Bay

VaeLuxuryEscape| *FreeBeachAccess|GATED|Central

Relax in Luxury – Free Beach & Pool Access! Unwind at this pristine North Coast retreat in a 24/7 gated community, just 5 minutes from Puerto Seco Beach—with FREE VIP beach & pool access! 🌞🏖️🌴 🔹 Booking Info: This listing is for a 1 bedroom (up to 2 guests). Need more space? Check out our other listings for larger bookings! 🌊 FREE VIP Experience: Enjoy swimming, sunbathing & VIP food/drink service at Puerto Seco Beach—compliments of Vaes Luxury Escape! Book your luxury tropical stay today! ✨

ValueLocationBathroom

4.79 out of 5 average rating, 63 reviews

Guest favourite

Villa in Runaway Bay

Ocean View • Pool • Pickleball • Gated | For 12

Welcome to Villa Palaav - A modern oasis in a private gated community Perfect for: • Birthday trips • Bachelor/Bachelorette groups • Family reunions • Friends trips • Retreats 🎉 Celebration Pkgs starting at US$350 This 6-bedroom Ocean View Villa features three 2 bedroom, apt-style King suites, each with private kitchens, 1–2 bath, and open-concept living areas, solar power, rainwater harvesting & smart cooling Amenities include: • Private pool • Pickleball court • Billiards room • Mini golf

FamilyValueComfort

4.95 out of 5 average rating, 43 reviews

Guest favourite

The exterior of a modern house is illuminated with colorful lights at night, highlighting its architectural features. Windows are framed by ornate grilles, and a slight incline leads to the entryway, surrounded by neatly trimmed greenery, creating a welcoming ambiance.

Home in Discovery Bay

Light House

Welcome to Light House, Escape to this modern 2 bedroom Home to enjoy with family & friends, gated community with security, located in Discovery Bay, St. Ann. Self Check in upon arrival. The home offers high speed internet, an old school game system with built-in Pac-Man & other games, streaming cable boxes in all rooms & a work station. Free Parking is also available. Light House is located minutes away from the famous Porto Seco Beach & Green Grotto Cave. Light House is a Home away from Home.

ValueFamilyHospitality

5.0 out of 5 average rating, 19 reviews

Top Guest favourite

A charming outdoor area showcases comfortable seating amid lush greenery. The inviting beach and turquoise sea are visible in the background, while a lantern adds a touch of character to the villa's exterior. The space is designed for relaxation and enjoying ocean views.

Villa in Duncans

Ocean Dreams Villa

Ocean Dreams Villa is a stylish, unique, beach villa with 3 bedrooms and 3 bathrooms and sets the stage for a memorable trip within steps of the beautiful Duncans Bay Beach (also known as Silver Sands Public Beach) with its sparkling turquoise waters and white silvery sand, the view is simply breathtaking. It's the perfect ambiance to relax in comfort, enjoy the breeze, listen to the birds, nature and let the soothing sound of the ocean waves breaking on the shore calm you and ease your mind.

FamilyValueAccuracy

4.94 out of 5 average rating, 126 reviews

Guest favourite

Villa in Discovery Bay

Ocean-view villa with private pool near beach

Welcome to Villa Amore, a spacious 5-star 3-bedroom villa with pool & stunning sea views! Features: ▪ Fully equipped kitchen & dining area perfect for family sharing. ▪ Spacious living room with direct access to your private pool ▪ Convenient shared guest bathroom Each bedroom offers: ▪ Private en suite bathroom for full comfort ▪ Balcony with stunning pool & sea views Relax in lush gardens with secure parking and just a short walk to Puerto Seco Beach - your perfect tropical retreat awaits!

ValueFamilyAccess

4.92 out of 5 average rating, 26 reviews

Guest favourite

A charming villa with a spacious covered patio is surrounded by lush greenery. The garden features tropical plants and a seating area with dark-finished furniture. Large windows provide natural light to the interior, while the double-story structure is enhanced by wooden accents and palm trees.

Villa in Ocho Rios

Private Seafront Villa near Ochi

Located directly on the ocean and room for 7 -- bring the Fam! Stylish Villa with three bedroom plus sleeper-den with four full bathrooms offers Caribbean charm and modern sensibilities. Full kitchen, super-comfy living area fronts an expansive dining/bar and lounge area with views of the sea that go on forever. Included: Starlink Wifi, a 65" SmartTV and a/c throughout; your private housekeeper/cook is there to take care of your every need. Enjoy a unique, relaxing Jamaican vacation today!

LocationValueQuiet

4.94 out of 5 average rating, 82 reviews

Guest favourite

Home in Browns Town

Swing Bed in the Hills: Secure Escape, Fast wifi

Tucked away in the cool hills above Browns Town, this bright villa blends indoor comfort with outdoor serenity. Our signature screened gazebo with swing bed is made for reading, napping, or stargazing; no bugs, just breeze. Inside: 2 king bedrooms, 2.5 baths, full kitchen, 75" TV, dedicated office, and fast Wi-Fi (136 Mbps). Outside: gated parking, local shops steps away, beaches 15 minutes away. Perfect for couples, families, or remote workers craving peace, privacy, and genuine Jamaica. 🇯🇲

LocationValueLong stay

4.85 out of 5 average rating, 47 reviews

Superhost

A shaded gazebo offers comfortable seating surrounded by lush greenery. Palm trees and vibrant foliage frame a view of the expansive lawn leading to the beach. The sea glimmers in the distance under a clear blue sky, creating a serene outdoor retreat.

Bungalow in Saint Ann

Kling Kling Beach House

Kling Kling is a beach house with a family feel, set within a large lawn running down to an almost fully private beach, a river for freshwater swimming, a reef for snorkelling, a fantastic housekeeper cook and a one of a kind man about the place. Just mins drive to shops or tourist facilities. Nearby scuba facilities, waterfalls, water parks, markets, tennis , golf, riding, the list goes on, both mainstream and off piste local. For more pics follow our Instagram: klingklingbeachhouse.

FamilyLocationKitchen

4.87 out of 5 average rating, 213 reviews

Top 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

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.

FamilyLocationAmenities

4.93 out of 5 average rating, 90 reviews

Top Guest favourite

Home in Discovery Bay

Courtyard by the Bay*Pvt Pool, BCH & 5-Star Amen

Escape to paradise to this beautiful built, luxurious, two-bedroom bungalow home in Discovery Bay. Discover a tropical haven with a private pool, modern comforts like FILTERED WATER and A1 amenities. Immerse yourself in island living and minutes away enjoy the 5 star resort style Puerto Seco beach, restaurants and major attractions. This place is suitable for all types of travelers seeking an unforgettable vacation. Look no further BOOK NOW at Courtyard by the Bay.

LocationValueCleanliness

4.96 out of 5 average rating, 195 reviews

Guest favourite

The exterior of Villa Oasis is showcased, set on a spacious lawn with well-maintained greenery. The ocean is visible in the background, while a gazebo with seating is located to one side. The main house features a light-colored facade and is framed by palm trees.

Villa in Discovery Bay

Villa Oasis: Modern/Private Beach/Oceanfront

Villa Oasis is a breathtaking getaway with modern amenities. Located in Discovery Bay, this oceanfront property sits on an acre of land, giving you a spacious home, the calming ocean breeze & amazing views for your dream vacation. Sitting conveniently between Montego Bay and Ocho Rios, this home’s access to so many popular tourist attractions makes it the ideal location for your Jamaica getaway. Guests of Villa Oasis also have access to a private beach.

LocationValueQuiet

4.81 out of 5 average rating, 81 reviews

Guest favourite

Home in Plantation Village

NEW~ Pool Access 3BR •Gated • Walk to the Beach

Welcome to your island getaway where laid-back coastal living meets modern comfort. This spacious 3-bedroom, 3.5-bath vacation home is perfectly designed for you with a quick stroll to the onsite private beach ✨ Why You’ll Love This Home ✔︎ Private beach access ✔︎ Secure gated community with 24/7 security ✔︎ Pool access ✔︎ Spacious, modern design ✔︎ Seamless self check-in via keypad ✔︎ Free on-site parking ✔︎ Fully air-conditioned

LocationFamilyPool

4.86 out of 5 average rating, 22 reviews