Middlesex Area Rentals
From $206 per night (USD)VRBO
Stylish 2-bedroom townhome with Ocean Views in enchanting Runaway Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover island elegance in this serene, stylish 2BR, 2.5BA retreat with sweeping ocean views. Designed for comfort and ...
From $206 per night (USD)VRBO
From $638 per night (USD)Expedia
exotic beach & villa with WiFi, AC in tranquil Tower Isle with pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
This 5-bedroom house in Tower Isle is perfect for your escape to paradise. With 7 queen beds and 2 twin bed2, guests wil ...
From $638 per night (USD)Expedia
From $128 per night (USD)VRBO
Adventure-Ready Beach Studio in Ocho Rios
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Start your Jamaican adventure from this beachfront studio right in the center of Ocho Rios! Dive into the large pool, hi ...
From $128 per night (USD)VRBO
From $108 per night (USD)Expedia
Glen Sea Inn of St. Mary - Charming 2 Bedroom Beachside Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Glen Sea Inn! Come enjoy a more peaceful side to the land of wood and water. Our home has been in the fam ...
From $108 per night (USD)Expedia
From $125 per night (USD)VRBO
Tandel Ocho Rios Apartment #2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Ocho Rios, this adorable apartment offers a tranquil escape for guests seeking comfort and ease. With one bat ...
From $125 per night (USD)VRBO
From $164 per night (USD)Expedia
Coastal Retreat. Beach life. Luxury 1 BR apartment at the Paradisiac Beach Club.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to your own luxe coastal retreat where comfort meets island elegance. This beautifully styled apartment offers th ...
From $164 per night (USD)Expedia
From $2401 per night (USD)VRBO
Ocean Front Staffed Villa | Lux Resort by Bocobay
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Palm Beach Villas in Runaway Bay, Jamaica is a new ultra-exclusive luxury beachfront villa community set along a stunnin ...
From $2401 per night (USD)VRBO
From $92 per night (USD)Expedia
Cozy 1 Bedroom with full kitchen and bathroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your home away from home! This comfortable and thoughtfully designed bedroom is perfect for solo travelers, c ...
From $92 per night (USD)Expedia
- From $105 per night (USD)
VRBO
Charming 1 or two bedroom apartments with WiFi in Lilly field Bamboo.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Consider this apartment your home away from home while you visit Bamboo. This charming space features 1 cozy bedroom wit ...
From $105 per night (USD)VRBO
From $393 per night (USD)Expedia
Blue Oasis @ Watermill Villas
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Kick back and relax in this calm, stylish space. With a short walk to the beach, this gorgeous two-story townhouse is ...
From $393 per night (USD)Expedia
From $1077 per night (USD)VRBO
Villa Esperanza @ Old Fort Bay, Ocho Rios
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Relax with the whole family at this peaceful place to stay. Villa Esperanza @ Old Fort Bay is a delightful and spacious ...
From $1077 per night (USD)VRBO
From $232 per night (USD)Expedia
Private Villa Paradise - Pool & Mountain Views
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
<p>Escape to Private Villa Paradise in the heart of Jamaica’s Manchester Parish! This spacious 6-bedroom, 4.5-bathroom r ...
From $232 per night (USD)Expedia
From $604 per night (USD)VRBO
Mammee Bay Estates Private Villa. 4 bed/4 bath; private pool. Access to beach.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The house is very spacious and clean with modern furnishings. All 4 bedrooms, living and dining rooms are equipped with ...
From $604 per night (USD)VRBO
From $167 per night (USD)Expedia
Charming studio with AC in picturesque Saint Ann's Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to a cozy studio in Saint Ann's Bay for a relaxing getaway. This awesome property features 1 comfy twin bed, perf ...
From $167 per night (USD)Expedia
From $234 per night (USD)VRBO
Cozy 3BR Villa w/ Poolside Gym, AC & WiFi near Ocho Rios
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover your perfect Jamaican escape in this spacious 3-bedroom, 2-bathroom home right beside the community pool and gy ...
From $234 per night (USD)VRBO
From $383 per night (USD)Expedia
Stay Exchange Modern Chill Retreat w/ Private Backyard Oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your laid-back escape in Ocho Rios - a modern, easygoing space designed for pure relaxation. This isn't just ...
From $383 per night (USD)Expedia
From $254 per night (USD)VRBO
New Cool Water Ocean Breeze Retreat Safe n Serene in Drax Hall
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the peaceful New Fairway Estate—just 10 minutes from nightlife, dining & shopping! Enjoy stunning mountain, ...
From $254 per night (USD)VRBO
From $190 per night (USD)VRBO
Cool Water Ocean Breeze in Serene Secure Community w/ Multiple Ensuite Bathrooms
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Drax Hall is waiting for you at this 1-bedroom 2-full bath villa. This awesome property features high ceilings. Enjoy 1 ...
From $190 per night (USD)VRBO
From $303 per night (USD)VRBO
A King-Queen Garden Escape Near Ocho Rios - Private 2-BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay a while and escape to this peaceful community to enjoy the beauty of nature and modern, here in the central part of ...
From $303 per night (USD)VRBO
From $131 per night (USD)Expedia
Relaxing modern 1-bedroom condo with pool in a gated Portmore Community.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Located at Bayfront Portmore, this condo is a dream. With 1 bedroom and a pull out sofa bed, guests can enjoy a cozy and ...
From $131 per night (USD)Expedia
From $88 per night (USD)VRBO
Peaceful 1-bedroom apartment with AC in charming Priory
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Priory, enjoy what this 1-bedroom apartment has to offer. This quaint space features a comfortable king bed, ...
From $88 per night (USD)VRBO
From $702 per night (USD)Expedia
Exotic 4-bedroom Villa at the beach in Ocho Rios
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This St. Ann Parish townhome boasts 4 inviting bedrooms. Each room is equipped with AC, a hair dryer, and an iron for yo ...
From $702 per night (USD)Expedia
From $172 per night (USD)VRBO
The View@ Sky Castles, Ocho Rios - cozy 1-bedroom w/views of Ocean & Ochi Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience Ocho Ros in this beautifully renovated 1-bedroom apartment with all amenities needed for a relaxing and comfo ...
From $172 per night (USD)VRBO
From $114 per night (USD)VRBO
Cozy Escapes 876: Secure 2BR with AC, Parking & near Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Cozy Escapes, a modern home in the newly constructed, gated community of Phoenix Park Village 2 in Portmore. ...
From $114 per night (USD)VRBO
From $140 per night (USD)VRBO
Sun-Filled Cozy House Near Beautiful Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The house is situated in a unique gated community and will comfortably accommodate a family, couple, a few friends or ju ...
From $140 per night (USD)VRBO
From $154 per night (USD)Expedia
Cozy 1-bedroom Bayfront Apartment in Portmore with Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Discover this 1-bedroom apartment in Portmore. The fabulous space features two queen beds and a cozy living room with a ...
From $154 per night (USD)Expedia
From $400 per night (USD)VRBO
Studio with private deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Keep it simple at this peaceful, family friendly and centrally-located place with its private deck. our guest can relax ...
From $400 per night (USD)VRBO
From $153 per night (USD)Expedia
2-bedroom bungalow in beautiful Ocho Rios gated community with AC.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to paradise in Ocho Rios at this beautiful bungalow. Guests will find two queen bedrooms and a living room with a ...
From $153 per night (USD)Expedia
From $306 per night (USD)VRBO
Charming 4-bedroom bungalow with WiFi, AC in lovely St. Ann Parish close to Ochi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Unwind in St. Ann Parish at this fabulous bungalow. With 4 bedrooms including 2 queen beds, 1 king bed, and 1 futon, gue ...
From $306 per night (USD)VRBO
From $108 per night (USD)Expedia
Cozy 1-bedroom apartment in Portmore with AC
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Your Portmore adventure begins at this 1-bedroom apartment. Inside, guests find a queen bed and a cozy living room with ...
From $108 per night (USD)Expedia
From $260 per night (USD)VRBO
Royal Escape Where Elegance Meets Comfort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Royal Escape- your Home away from Home. At Royal Escape, comfort meets elegance. The perfect blend of lu ...
From $260 per night (USD)VRBO
From $251 per night (USD)Expedia
Beautiful 2-bedroom house with AC in charming St. Ann Parish
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of St. Ann Parish from this enchanting 2-bedroom house. Inside, guests find two cozy queen beds and ...
From $251 per night (USD)Expedia
From $958 per night (USD)VRBO
Tropical Private Oasis Home in Tower Isles St Mary
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to this wonderful house in picturesque Tower Isle. With five spacious bedrooms and seven bathrooms, guests enjoy ...
From $958 per night (USD)VRBO
From $144 per night (USD)Expedia
Welcome to Spring Dash,2BR POOL&BEACH ACCESS+VIEW,FREE PARKING,BAR&Grill, &AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This relaxing 2-bedroom retreat offers stunning beach views and the perfect blend of comfort and Caribbean charm. Wake u ...
From $144 per night (USD)Expedia
From $149 per night (USD)VRBO
WECOME TO SPRING DASH 2BR POOL&BEACH ACCESS. BAR& GRILL, FREE PARKING&AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your island escape in beautiful Discovery Bay, Jamaica! This relaxing 2-bedroom retreat offers stunning beac ...
From $149 per night (USD)VRBO
From $100 per night (USD)VRBO
Welcome to Island Breeze Retreat. Comfort meets the warm spirit of Jamaica.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step inside and enjoy a clean, cozy apartment cooled by the natural island breeze. Relax in a comfortable living area, s ...
From $100 per night (USD)VRBO
From $108 per night (USD)VRBO
The Scarlett Escape: Charming 3BRD Oasis house Edgewater Portmore with AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 3-bedroom Portmore house. The beautiful bedrooms feature a queen bed, a full bed, and a tw ...
From $108 per night (USD)VRBO
From $182 per night (USD)Expedia
Aurelia- 1BR Luxury Beachfront Condo at Paradasiac Beach Club
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked into a peaceful coastal setting at the Paradisiac Beach Club, this calm retreat offers a thoughtfully designed on ...
From $182 per night (USD)Expedia
From $174 per night (USD)VRBO
Sun, Sea & Serenity 2 BR Stay at Sun Haven Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Forget your worries in this spacious and serene space. This 2-bedroom, 2-bathroom suite at Sun Haven Villa offers a cozy ...
From $174 per night (USD)VRBO
From $86 per night (USD)VRBO
Sun, Sea & Serenity 1 BR Stay at Sun Haven Retreat
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this calm, stylish space. Lower Level – 1 Bedroom / 1 Bathroom Enjoy privacy and comfort in this ...
From $86 per night (USD)VRBO
From $360 per night (USD)VRBO
Sun, Sea & Serenity 5 BR Stay at Sun Haven Retreat
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Sun Haven Villa Retreat! Escape to island-style luxury at Sun Haven Villa Retreat, a modern and spacious va ...
From $360 per night (USD)VRBO
From $239 per night (USD)VRBO
Sun, Sea & Serenity 3 BR Stay at Sun Haven Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Forget your worries in this spacious and serene space. Relax in the upper level or lower level of Sun Haven Villa, featu ...
From $239 per night (USD)VRBO
From $155 per night (USD)VRBO
Cozy Haven
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful designed chic townhouse nestled in a secure gated community offers a luxurious escape with bold interiors ...
From $155 per night (USD)VRBO
From $158 per night (USD)Expedia
Cozy 2-bedroom apartment in enchanting Spanish Town with AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Get ready to relax in this 2-bedroom apartment in Spanish Town. The space offers a pleasant atmosphere with air conditio ...
From $158 per night (USD)Expedia
From $94 per night (USD)VRBO
Cozy 1-bedroom bungalow in pleasant Greater Portmore with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to this charming bungalow in Greater Portmore. This cozy retreat features one bedroom with a comfortable queen b ...
From $94 per night (USD)VRBO