Vacation rentals with a kayak in Jamaica

Oceanfront 4BR Villa w/ views Pool Beach Staff

Sea Haven is a charming Jamaican villa set within one acre of private waterfront on the edge of incredible Discovery Bay, a horseshoe of blue crystal clear water, known locally as "Millionaire's Row & the "Riviera". Designed for both relaxation and play, our home benefits from a man made perched beach, steps into the Caribbean sea, large floating raft, kayaks, paddle boards, great snorkeling, private pool. Full staff including Chef. Guests receive complimentary access to Puerto Seco Beach Club.

Outdoor spaces · Indoor spaces · Cleanliness

"Smallah" 4-br seaside villa own pool, resort area

Welcome to Smallah Villa, our spacious and elegantly designed 4-bedroom, 4.5-bathroom oceanfront townhouse in the Freeport Area of Montego Bay! This stunning property is the perfect getaway for families or groups of friends looking for a relaxing retreat in Caribbean Paradise. It comfortably accommodates up to 10 guests. With private infinity pool and a pier for private boat pickup. Premium Services ($ - Additional Fee) • Grocery Shopping & Delivery Service ($) • Cook & Clean ($) • Driver ($)

Value · Outdoor spaces · Cleanliness

C-Vue Villa *Pool*AC*Gated*Sea Front*

Get away to C-Vue Villa where the tranquil sound of the waves become your lullaby for a good night's rest. You can then wake up to a picturesque view of the sunset over the ocean. The location is full of amenities for you to enjoy, these include the *pool, *basketball court, *kiddies play area and your own private *trampoline for the kids. Full *AC Rooms, *Blankets, fast *WIFI, free *Parking, smart *TV.............. C- Vue Villa will allow you to relax, unwind, de-stress and feel rejuvenated.

Outdoor spaces · Location · View

Storeroom Cabin by the Sea | Roots. Rustic. Relax.

Where good vibes are re-stored! Once a working storeroom, this space has been transformed into a rustic, scenic cabin for travelers seeking a unique, off-the-beaten-path experience. Sustainably converted in 2024 using local wood and sea stones, the cabin was designed to capture the Caribbean Sea’s breezes and views. Unwind on the wraparound porch. Gaze at the stars while bathing in the indoor/outdoor shower. With a roots-rock-reggae Jamaican vibe, this cabin offers a relaxed escape to nature.

Value · Outdoor spaces · Breakfast

Wake Up 15ft From the Sea · Chef · Reef Ocho Rios

Fifteen steps from your deck to the Caribbean Sea. Peacock Villa is a beachfront retreat built from local guango and cedar with your private chef services included. Dine on the deck or beach — choose from our à la carte menu or purchase your own groceries market-fresh, your choice. Swim seven minutes to a coral reef. Snorkeling gear, paddleboard and kayak all provided. Queen bed, air conditioning, housekeeping included. Sleeps 2. Ocho Rios markets, restaurants and shops — all walkable.

Outdoor spaces · Location · Cleanliness

Paradise Penthouse w/ Private Chef & Oceanfront

🌞 2026 Summer Discount. Skip the Resort 🌞 Escape to Paradise Penthouse in the heart of Ocho Rios! This 3 story oceanfront gem is nestled in the exclusive, 24 hour gated community of Crystal Cove, offering the ultimate tropical getaway. Relax in style with stunning ocean views, chef prepared breakfast and dinner , access to a driver, and endless comfort. Perfectly located on Main Street, you’re minutes away from local culture and adventure. Your dream Jamaican vacation awaits!

Location · Outdoor spaces · Condition

Cliff's Hideaway Retreat Negril

Experience our clifftop sanctuary with ocean views and a private reef. It includes two updated bedroom cabins with baths (one with a tub), a main lodge featuring a kitchen, bar, and pool table, fast wifi, and garden paths to a sea-access cave. Amenities include a guest bathroom, secure parking for two, and for 2023, RO-filtered drinking water and upgraded AC. -- The entire secure space, including cave sea access is privately yours! Private chef + local shopper on request.

Outdoor spaces · Value · Decor

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.

Value · Outdoor spaces · Laundry

Snorkeler's Cove - Negril, Jamaica

Welcome to your Jamaican paradise, a hidden gem perched atop a picturesque cliff overlooking the breathtaking Caribbean Sea. Nestled within the exclusive gated community, Little Bay Country Club, this newly renovated home offers a slice of island heaven. Your own private furnished cabana beckons, as well as the leisurely stroll to the world-famous 7-mile beach. With every sunrise at Snorkeler's Cove, you'll be greeted by a barrage of colors painting the horizon.

Outdoor spaces · Location · Bathroom

Oceanfront Off-Grid Beach House | Portland

Escape to a secluded oceanfront, off-grid beach house in Portland, Jamaica. Wake to Caribbean Sea views, step onto the black-sand beach, swim, kayak or relax beneath the coconut trees. Perfect for families and groups, the home offers spacious bedrooms, comfortable living areas, a full kitchen, pool and outdoor dining overlooking the sea. Fully solar-powered and surrounded by nature, it’s a private tropical escape where the ocean is always just steps away.

Location · Family · Comfort

Private Beach | Pool | 24hr Security | ACs | Wi-Fi

Escape to our 2-bed, 2.5-bath townhouse in Negril's exclusive Little Bay Country Club. This private retreat in a gated, beachfront community offers access to a private beach, pool, and tennis court. Perfect for a relaxing Jamaican getaway, it comfortably accommodates small groups or families seeking both tranquillity and proximity to Negril's vibrant attractions. Enjoy stunning sea views and modern amenities in a secure, serene setting.

Location · Outdoor spaces · Wifi

Central Beachfront Bungalow

This special place is uniquely located in a paradise cove steps away from the city center, where you can find all the best restaurants and bars. Grab a kayak & enjoy the sparkling coastline with the number one snorkeling spot just in the backyard. From nightlife to river excursions we’ve got you covered. Experience what it feels like to be a local in Ochi by staying in this double door, cottage style, ocean view residence.

Value · Outdoor spaces · Parking