Smoking friendly vacation rentals in Saint Ann

4.92 out of 5 average rating, 38 reviews

A serene beach scene is highlighted, featuring soft sand and gentle waves. Two sun loungers are positioned under the shade of palm trees. A vibrant kayak with passengers glides through the clear, sparkling water, capturing the essence of outdoor leisure.

Villa in Ocho Rios

Beachfront Villa · Private Chef · Ocho Rios

Eden Sands is a beachfront sanctuary in Ocho Rios, handcrafted from local guango and cedar. Wake up to waves, step onto your private deck surrender to Jamaica completely. Your world-class chef is included — bold Jamaican soul food and international cuisine served on the deck or beach. À la carte or market-fresh, your choice. Swim seven minutes to a stunning coral reef. Snorkel gear, paddleboard and kayak all included. Two bedrooms, sleeps 4. Air conditioning and housekeeping included throughout.

4.64 out of 5 average rating, 22 reviews

A spacious bedroom features large windows that allow natural light to fill the room. A vibrant yellow bedspread covers a spacious bed, complemented by natural wooden furnishings. A round table and woven rug enhance the earthy decor, while lush greenery is visible through the windows.

Condo in Gayle

Eco Cottage With Private River

Discover your private tropical sanctuary surrounded by lush gardens and hummingbirds. Unplug and unwind in a spacious, bright apartment with a king bed, kitchenette, spring water shower, outdoor bath, hammock, fire pit, and yoga area with hanging seats. Explore nearby waterfalls & beaches for a peaceful nature escape. Nestled in St. Mary’s scenic mountains, just 40 minutes from Ocho Rios or Ian Fleming Airport , this gated retreat offers the perfect blend of rustic comfort, peace and adventure.

4.85 out of 5 average rating, 46 reviews

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. 🇯🇲

4.81 out of 5 average rating, 36 reviews

Villa in Discovery Bay

10 min to Runaway Bay Beach-Full Kitchen-BBQ

Set on 44,000 ft² / 1-acre in Discovery Bay, 3 min → Bengal Beach (15 min walk) ✓ Superhost care + 4.8★ average, 29 reviews ★ Extremely safe, community ✓ Free early check-in ✓ 1 hr ✈ Montego Bay Airport (MBJ) ✓ Dinning table for 6, family gatherings welcome ✓ Full equipped + Stocked kitchen ✓ Flexible visitor policy ✓ Surround sound in ceiling ✓ Rooftop terrace, outdoor seating & treetop views ✓ Meals by in-home chef available ★ “The rooftop seating provided a great view of the greenery.”

4.93 out of 5 average rating, 68 reviews

A charming house with bright orange walls is framed by a green hedge and a decorative white gate. An awning in striped yellow and green provides shade over the front porch, where vibrant plants add color. A clear blue sky and clouds fill the backdrop.

Home in St. Ann Parish

Stunning 2 bed 1 bath, Greenwich Estate, Drax Hall

Looking for a home away from home that is not only affordable but is also located within close distance of the many attractions Jamaica has to offer while still being a place where you can kickback, hold a vibes and get the full Jamaican experience. If that is what your seeking then look no further than Little Piece Of Irie which is located in the community of Greenwich Estate, Drax Hall.you'll enjoy the comfort and fun that no stuffy hotel could provide and at a fraction of the cost.

Earthen home in Runaway Bay

A sparkling outdoor swimming pool is surrounded by lush tropical foliage and vibrant flowers. A shaded seating area is visible near the pool, offering a tranquil spot to relax. Blue skies add to the serene atmosphere of this inviting outdoor retreat.

4.94 out of 5 average rating, 77 reviews

Rustic 1BR Cottage | Pool + Minutes Walk to Beach

Escape to our eco cottage where nature meets comfort. Our cozy 1BR cottage offers the perfect mix of rustic charm & modern comfort, complete with A/C, hot water & WiFi. Lounge by the pool, soak in the tropical surroundings, & enjoy the laid-back vibes of our little paradise. Whether you’re craving adventure or pure relaxation, you’ll find it here. Come unwind, explore, & experience the beauty of Jamaica—your island escape awaits! Book now & experience Casas de Tierra Jamaica!

4.96 out of 5 average rating, 112 reviews

A charming outdoor deck features several light blue bar stools, arranged around a raised bar area with an umbrella for shade. The wooden structure of the cabin is visible in the background, surrounded by lush greenery and a clear sky.

Cabin in Runaway Bay

A/C cabin outdoor jacuzzi, access to private beach

Take a visit to the historical city of Runaway Bay, St. Ann. Stay at the Cozy Cabin and experience a piece of this historical city. The cabin is nestled in the cool hills of Runaway bay. It is yet, conveniently located just 5 - 10 minutes drive from world renowned restaurants and excursion experiences. Kick back and relax in comfort and style. Get the best of both worlds: the magical Runaway Bay mountains and the beautiful Caribbean sea. A vacation you will never forget!

4.95 out of 5 average rating, 43 reviews

An outdoor seating area is highlighted by plush chairs arranged around a small table. A vibrant plant with yellow flowers sits in a red pot, adding a touch of color. Lush greenery is visible through large windows, providing a serene backdrop.

Home in Priory

KK'S Elite Escape with private beach/gated/pool

KK's Elite Escape is nested in the middle of paradise. It is located in the prestigious Richmond Estates Community that prides itself of natural beauty and sustainability. The property is beautifully decorated with palms and other flora and is only 6 minutes away from a private beach. It is also within 20 minutes of several attractions such as Chukka, Dolphin and Plantation Cove and Dunn'sRiver. Come relax with the whole family at this peaceful place.

4.97 out of 5 average rating, 140 reviews

An aerial view captures a coastal area featuring vibrant green landscapes, urban structures, and a serene bay. The coastline is dotted with boats, and a variety of buildings, including a hotel, is visible along the shore, highlighting the proximity to both nature and amenities.

Apartment in Ocho Rios

SCH Airbnb Mystic Ridge Resort

Come to SCHAirbnb at Mystic Ridge Resort for a spacious, family friendly atmosphere. Comfortably sleeps up to four people, with kitchen, wifi with TV in bedroom and living room. Access to pool and tennis court. Located 2.4km from Mytic Mountain and about 10 minutes walk from Ochi Rios Bay beach. Close to restaurants and transportation. Excellent picturesque view of the city.

4.85 out of 5 average rating, 391 reviews

Apartment in Ocho Rios

The Coconut Palm Villa ~ Idyllic Ocean View Suite

Escape to this private ocean-view retreat in Ocho Rios. Perfect for couples or solo travelers, this peaceful hillside getaway offers comfort, privacy, and beautiful scenery—just minutes from beaches, restaurants, and attractions. Enjoy air conditioning, fast Wi-Fi, hot water, and a refreshing shared pool. Private airport pickup and tours are also available.

4.99 out of 5 average rating, 551 reviews

A fully refurbished cut stone cottage sits amidst lush tropical greenery, featuring a shaded verandah adorned with colorful cushions. Stone walls complement the natural surroundings, while palm trees and vibrant foliage create a serene retreat atmosphere.

Cottage in Ocho Rios

"Tumbleweed Cottage"

Quiet very private one bedroom fully refurbished cut stone cottage with your own pool. Located less than a mile from Upton (Sandals) Golf Course. Ideal for Golfers, Writers, Painters and Weekend Travelers.