Vacation rentals with outdoor seating near Doctor's Cave Beach

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Top-rated outdoor seating rentals near Doctor's Cave Beach

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Guest favorite

A serene view is captured from a pool area, showcasing lush tropical plants and a glimpse of the ocean in the distance during sunset. The sky is adorned with soft hues, reflecting on the water's surface, creating a calming atmosphere.

Home in Reading

5 out of 5 average rating, 12 reviews

Whiterock Montego Bay Bou Villa

Spend memorable moments at our quiet oasis with Royal Palm trees, gardens, Jerk grills for outdoor cooking or just sit in the garden and enjoy the wind chime as it's soothing melody chimes as the winds blow. View of the Courtyard and open skies. Take a stroll down hill then up our spiral stairs to our elevated pool. Enjoy stunning ocean, mountain and city views from the pool deck. Or watch the sunset from the Floating Deck. Whatever your choice, you will enjoy the natural beauty. Whiterock.

Guest favorite

A pair of lounge chairs is positioned on a wooden deck, overlooking a lush green landscape. The infinity pool can be seen at the edge of the deck, with a backdrop of rolling hills under a cloudy sky.

Condo in St. James Parish

4.89 out of 5 average rating, 133 reviews

Luxury In Paradise: Pool, Jacuzzi, Gated, 3rd Flr

Whether you’re in Jamaica for work or vacation, this condo will check all your boxes. Located in Ironshore, one of Montego Bay’s most prominent communities, sits Dream 36. A luxury condominium complex that’s close to entertainment, beaches, restaurants, and airport (12 mins). This one bedroom condo is extremely spacious at 900 sq ft. It boasts modern furnishings with a warm feel. You can truly relax with amazing amenities such as gated 24/7 security, lounge, pool, and rooftop views. Book now 😁

Top guest favorite

A serene pool area is visible, featuring lounge chairs arranged beside a clear blue pool. Palm trees and lush greenery frame the space, while a covered gazebo is provided in the background, enhancing the outdoor relaxation experience.

Townhouse in Montego Bay

4.98 out of 5 average rating, 178 reviews

2BR Townhouse with staff, gym, pool & beach access

Escape@20 is a lovely townhome that guarantees a truly relaxing and memorable experience. A friendly housekeeper/cook is included at NO EXTRA COST!! You just need to purchase the groceries. The townhome has an open floor plan with living and dining room opening out to a covered patio and a backyard. Guests can enjoy breathtaking views of the neighboring yacht docking area, swimming pool, gazebo/bbq grill space, gym, playground for kids, 24 hour security and complimentary beach access nearby.

Guest favorite

An expansive view of the Caribbean Sea is captured from the rooftop patio, highlighting the serene blue water and sandy beach. Lush greenery borders the shoreline, while distant hills provide a picturesque backdrop under an overcast sky.

Condo in Montego Bay

4.82 out of 5 average rating, 144 reviews

Panoramic Studio with Ocean & Mountain Views

Wah Gwan, a.k.a "What's going on? " Come and stay at my newly updated condo!! It is in a great spot, close to all the action and Harmony Beach! It has a great view on the private 3rd floor, it is a good size & can accommodate 4 people with a mini separate bedroom area, blocked off by curtains. I love the full size fridge, the night views, (especially down by the pool area). I love that you can get a beer or a meal anytime. We also have a Mini Mart on the property!! You will enjoy your stay:)

Guest favorite

A cozy sleeping area features a spacious bed with dark bedding, complemented by red and black curtains. A modern glass shower is visible in the corner, surrounded by stone walls. Soft lighting from a bedside lamp creates a relaxing ambiance.

Apartment in Montego Bay

4.9 out of 5 average rating, 10 reviews

A & G Peace & Serenity

Discover the perfect blend of comfort and convenience in this stylish Studio apartment! Ideal for couples, business travelers, or solo explorers, this inviting space is close to the city, and within walking distance of restaurants, entertainment, and other amenities. Whether you're here for a quick getaway or an extended stay, this one-bedroom apartment offers all the comforts of home in an unbeatable location. Transportation is available at a cost for your excursions and entertainment.

Top guest favorite

A tranquil outdoor swimming pool is set amidst lush tropical landscaping, featuring sun loungers with cushions positioned around the water. A wooden deck extends into the pool, offering direct access. Behind, large windows of the condominium reflect the serene bay views under a clear blue sky.

Condo in Montego Bay

4.95 out of 5 average rating, 141 reviews

1br Lux Oceanfront Apt Pool Beach Gym Pickleball

Discover the ultimate tropical retreat at the Soleil Residences, where luxury meets serenity. This elegant oceanfront one-bedroom condominium features a stunning balcony with 180-degree views of the Bay, inviting you to bask in the beauty of Jamaica's coastline. Highlights - Lge Waterfront Pool & Pool Deck * Private Beach Access * Gym * Tennis/Pickleball* Kids Play Area * Gated Community * Fast Fibre WiFi* Chef on request * Spa Services * Concierge Services * Full Time Driver Upon Request

Guest favorite

A spacious living area features elegant bamboo furniture, including a two-seat sofa and comfortable chairs. Natural light floods in through large windows, highlighting decorative elements like a starburst mirror and potted greenery. A textured rug anchors the space, with a coffee table positioned centrally.

Apartment in Montego Bay

4.94 out of 5 average rating, 127 reviews

2BR Getaway w/Pool, Near Beach in Montego Bay

This gorgeous apartment has been furnished to feel like a true getaway. It’s the ideal retreat for an adventurous & up-scale stay, located in a gated community that is close to the absolute heart of Montego Bay. We believe it’s the ultimate location to experience this part of the island. At only 10 minutes walking distance from Doctor's Cave Beach and the main Hip Strip, you will be very close to all the action. Settle in by zoning out with family or friends and enjoy your getaway.

Guest favorite

A cozy sitting area features a blue, modern sofa positioned against a wall. Light-colored flooring complements the neutral walls, while a small doorway with a wooden frame adds depth. An abstract artwork hangs above the sofa, providing a splash of color to the serene space.

Apartment in Montego Bay

4.94 out of 5 average rating, 31 reviews

Apartment 5 @ Top Bay Apartments

Welcome to Apartment 5 at Top Bay Apartments—a cozy and stylish retreat in the heart of Montego Bay. This charming space offers all the comforts you need for a relaxing stay, including a fully equipped kitchen, comfortable living area, and a peaceful atmosphere that feels like a true home away from home. Located in a quiet, friendly neighborhood on Upton Hill, Apartment 5 puts you just minutes from Montego Bay’s beautiful beaches, vibrant markets, and popular local restaurants.

Top guest favorite

A charming two-story pink house is surrounded by lush green grass and tropical plants. Tall palm trees provide shade, and a walkway leads to the front entrance. A water tank is visible on the roof, enhancing the functional aspect of the property.

Guesthouse in Montego Bay

4.97 out of 5 average rating, 104 reviews

Always Home

This cozy and private hideaway is located in Bogue Village Montego Bay minutes away from Sangster International Airport, restaurants and shopping center. Although off the beaten path you'll want for nothing. Fantastic for first time or returning vacationers. The outdoor area is equipped with seasonal fruits, BBQ area, swing,hammock, green area, outdoor dining and privacy. The chirping birds, awesome sun rise and sunset add tranquility and peace of mind to each day.

Superhost

A clear blue pool reflects the sky, surrounded by lush palm trees and verdant foliage. A covered bar area with seating is located nearby, providing a shaded space for relaxation. The calm atmosphere of the gated community is evident in this inviting outdoor setting.

Apartment in Montego Bay

4.8 out of 5 average rating, 205 reviews

Seawind On The Bay Montego Bay Studio

Seawind On The Bay is a safe gated community. The property has a pool and shared bar and grill with a covered community centre. The beach is a short distance away beside Secrets Hotel. A spectacular view of Montego Bay Harbor with cruise ships awaits you. Montego Bay Yacht Club is next door with great food and bar. Also, within walking distance is Secrets Wild Orchid, Breathless Resorts and Spa. Montego Bay Cruise Ship terminal less than 2 miles away.

Guest favorite

A bright and airy studio space features a spacious bed with patterned pillows, complemented by a cozy seating area adorned with decorative cushions. Natural light filters through a large window, showcasing lush greenery outside. A stylish light fixture adds a modern touch to the ambiance.

Apartment in Montego

4.94 out of 5 average rating, 140 reviews

SERENITY ON THE BAY

Serenity On The Bay is located on the exclusive Freeport Peninsula, nestled between The Secrets and Sunscape Resorts. This is a safe community. The Montego Bay Yacht Club offers fine dining and an excellent bar, property borders the club. Along the Peninsula, there is a jogging trail, for your early morning or sunset run. At Serenity On The Bay one can take opportunity to visit the attractions/adventures as well as relaxation at every turn.

Guest favorite

A screened-in patio area features an outdoor dining table with black metal chairs. Potted plants add greenery, and a gentle view of the Caribbean Sea is visible through the large windows, allowing natural light to fill the space.

Condo in Montego Bay

4.94 out of 5 average rating, 111 reviews

1 Bdrm. Ocean view Condo, Sea Castles, Montego Bay

Light, airy condo caressed by the cool breeze from the Caribbean Sea. The Condo boast as breathtaking view of the Caribbean Sea the area is quiet and peaceful and allows for relaxation for the busy traveller. The condo is fully contained with all the amenities needed to keep you comfortable throughout your stay.