Saint Mary, Middlesex Area Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Saint Mary, Middlesex Area on RentalSaver.com!

Saint Mary Rentals

From $89 per night (USD)
VRBO
Cozy 1-bedroom apartment in fantastic St. Mary Parish with AC, WiFi & Oceanviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Escape to this charming apartment in picturesque St. Mary Parish. This gorgeous rental features 1 bedroom with a king be ...
From $89 per night (USD)
VRBO
From $60 per night (USD)
Expedia
Charming studio with AC and WiFi in amazing Oracabessa
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Get ready to relax in this brilliant studio in Oracabessa. This adorable property features 1 cozy bedroom, perfect for u ...
From $60 per night (USD)
Expedia
From $117 per night (USD)
VRBO
Cozy 1 Bedroom Apartment with outside pool 10 minutes from Ocho Rios
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Pimento Apartment is a one bedroom (1 double bed, 1 single), one bathroom apartment with a kitchen and seating area. ...
From $117 per night (USD)
VRBO
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Expedia
Tremendous 7-bedroom estate in Tower Isle with AC, WiFi
Bedrooms:
7
Bathrooms:
7
Sleeps:
15
Your cozy getaway awaits in Tower Isle at this pleasant estate. With 7 welcoming bedrooms, this property is perfect for ...
Click For Pricing
Expedia
From $108 per night (USD)
VRBO
Beyond View Villa/Private Pool/Transportation/Chef Three Hills Tower Isle
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beyond View Villa offers a 360-degree view of lush mountainsides and stunning sea vistas, allowing guests to wake up to ...
From $108 per night (USD)
VRBO
From $207 per night (USD)
Expedia
Whispering seas villa
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Whispering seas a beautiful property with an amazing ocean view with all the amenities for your comfort. Breath taking m ...
From $207 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Crystal Resort. 5 mins from beach, 15 Mins to Ocho Rios Centre , Secure, CCTV.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This luxurious ground floor apartment at the Crystal Resort with infinity pool has breath taking views, only 5 mins fro ...
From $181 per night (USD)
VRBO
From $704 per night (USD)
Expedia
Luxe 7-bedroom villa - WiFi, AC in phenomenal St. Mary Parish min from Ocho Rios
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Discover Paradise at Our Luxury Oceanfront Villa in Ocho Rios, Jamaica Escape to the tropical haven of your dreams at ...
From $704 per night (USD)
Expedia
From $73 per night (USD)
VRBO
Lee By The Sea
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
About this space Keep it simple at this peaceful and centrally-located place. 15 mins away from Ocho Rios and 10 mins fr ...
From $73 per night (USD)
VRBO
From $2266 per night (USD)
Expedia
Luxury Oceanfront Villa~ Fully Staffed~Pool~Jacuzzi~Movie Theatre
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Vista Royale is a luxurious oasis nestled in a beautiful paradise. Vista Royale is a majestic 6 bedroom villa that redef ...
From $2266 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Luxury Villa - Private Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
In the heart of a Jamaican community off the beaten track, a villa offering outstanding luxury with amazing views out ov ...
From $446 per night (USD)
VRBO
From $80 per night (USD)
Expedia
Soothing 1-bedroom studio in Oracabessa
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your Oracabessa adventure begins at this charming studio. This lovely space offers a cozy bedroom and a private bathroom ...
From $80 per night (USD)
Expedia
From $805 per night (USD)
VRBO
Cozy 2-bedroom apartment with AC, WiFi in Pleasant St. Mary Parish
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
St. Mary Parish is waiting for you at this marvelous 2-bedroom apartment. This charming space features 1 queen bed and 1 ...
From $805 per night (USD)
VRBO
From $75 per night (USD)
Expedia
Dad's Place - Where Comfort and Community Meet !
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the best of both worlds at Dad’s Place—a cozy retreat in Annotto Bay, Jamaica, where city life meets country ...
From $75 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Condo in Tower Isle
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to the peaceful haven of Tower Isle, where tranquility meets nature in perfect harmony. Nestled along the coastli ...
From $181 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Unique mosaic 2-b/r eco-friendly open concept space-WiFi, seawater pool, BBQ
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in a remote village in Robins Bay, this delightful apartment offers a welcoming atmosphere for guests. With 2 op ...
From $229 per night (USD)
Expedia
From $900 per night (USD)
VRBO
Oceanfront, Cook, 15min OchoRios, Butler, Housekeeper, Kayaks and Snorkels, Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Villa Hestia is your private oceanfront villa in Boscobel — just 15 min from Ocho Rios and opposite Ian Fleming Internat ...
From $900 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Spacious Oceanview Home: The Perfect Venue for Special Events & Large Groups
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Our country-style 6-bedroom house is ideal for large groups or families, featuring 5 full beds, 2 king beds, and 2 twin ...
From $331 per night (USD)
Expedia
From $80 per night (USD)
VRBO
Jireh's Place - Charming 1-bedroom apartment in peaceful Whitehall Estate
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Get ready to relax in this 1-bedroom apartment in Whitehall Estate, Saint Mary. This serene retreat features 1 queen bed ...
From $80 per night (USD)
VRBO
From $295 per night (USD)
Expedia
The Idyll - Fully Renovated 3-bed 3.5 Bath Condo in Ocho Rios with AC & Wi-Fi
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Don't worry about a thing at this tropical oasis. 15 minutes away from Ocho Rios in the gated Tranquility Cove Developme ...
From $295 per night (USD)
Expedia
From $129 per night (USD)
VRBO
Bleu Haven oceanfront 6 bedroom in Tower isle
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
About this space One room in a six bedroom apartment located on the elegant corridor in Boscobel The space Tastefully de ...
From $129 per night (USD)
VRBO
From $14750 per night (USD)
Expedia
The Tropical Nest, Ocho Rios, Jamaica
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Tropical Nest is a charming private beachfront oasis located at Chrisann’s Beach Resort, 7 -10 minutes away from the ...
From $14750 per night (USD)
Expedia
From $114 per night (USD)
VRBO
Chic Modern 1BR at Milan The Manor – Cozy and Stylish Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Experience the best of Ocho Rios from Milan the Manor 6A, a centrally located retreat just minutes from top attractions. ...
From $114 per night (USD)
VRBO
Click For Pricing
Expedia
3 bedroom beachfront apartment, Tower Isle, 24hrs security, beach, pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Escape to this adorable beach front apartment in picturesque Tower Isle, it has 24hrs security and free parking. With 3 ...
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Expedia
From $69 per night (USD)
VRBO
6-bedroom studio in welcoming Ocho Rios with WiFi, AC Escape to Tranquility
Bedrooms:
6
Bathrooms:
6
Sleeps:
2
Stay comfortably in Ocho Rios at this marvelous 6-bedroom studio. Each room features either a queen or king bed, ensurin ...
From $69 per night (USD)
VRBO
From $157 per night (USD)
Expedia
NEW BUILT | 3BR | Ocho Rios 15mins | Beach 10mins | 24HR Gated | Family Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
***** FALL 2025 PROMO ***** FALL 2025 STAY BOOKINGS OF 7+ DAYS WILL BE GIVEN 1 DAY COMPLIMENTARY BEACH ACCESS TO PLEASUR ...
From $157 per night (USD)
Expedia
From $80 per night (USD)
VRBO
Grace Garden Guesthouse - 1 queen Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
At Grace Garden Guest House One Love is everything. We're perfectly located in Ocho Rios Jamaica, We accommodate both bu ...
From $80 per night (USD)
VRBO
From $88 per night (USD)
Expedia
Grace Garden Guesthouse - 2 Queen studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
At Grace Garden Guest House One Love is everything. We're perfectly located in Ocho Rios Jamaica, We accommodate both bu ...
From $88 per night (USD)
Expedia
From $80 per night (USD)
VRBO
Grace Garden Guesthouse -2 King duplex studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
At Grace Garden Guest House One Love is everything. We're perfectly located in Ocho Rios Jamaica, We accommodate both bu ...
From $80 per night (USD)
VRBO
From $340 per night (USD)
Expedia
4-bedroom house in lovely Tower Isle with pool, fitness room, AC, WiFi
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Are you looking for a place to relax and unwind? Get ready to be enchanted in this beautiful, quiet 4-bedrooms, 3-baths ...
From $340 per night (USD)
Expedia
From $95 per night (USD)
VRBO
Grace Garden Guesthouse -1 BR Studio 3
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
At Grace Garden Guest House One Love is everything. We're perfectly located in Ocho Rios Jamaica, We accommodate both bu ...
From $95 per night (USD)
VRBO
From $86 per night (USD)
Expedia
Grace Garden Guesthouse -1 BR Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
At Grace Garden Guest House One Love is everything. We're perfectly located in Ocho Rios Jamaica, We accommodate both bu ...
From $86 per night (USD)
Expedia
From $95 per night (USD)
VRBO
Grace Garden Guesthouse -1 BR Studio 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
At Grace Garden Guest House One Love is everything. We're perfectly located in Ocho Rios Jamaica, We accommodate both bu ...
From $95 per night (USD)
VRBO
From $119 per night (USD)
Expedia
The Willow Apartment
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
About this space The Willow Apartment is located 15 minutes from the town of Ocho Rios. Nestled in the beautiful hills o ...
From $119 per night (USD)
Expedia
From $470 per night (USD)
VRBO
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 $470 per night (USD)
VRBO
From $72 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 $72 per night (USD)
Expedia
From $141 per night (USD)
VRBO
Beachfront 2-bedroom Apartment in Tower Isle
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Tower Isle apartment boasts 2 inviting bedrooms. The charming decor and lovely ambiance make guests feel right at h ...
From $141 per night (USD)
VRBO
From $365 per night (USD)
Expedia
Island Getaway
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Why be trapped in a hotel when you can stay here! This stylish place to stay is perfect for group trips. Conveniently lo ...
From $365 per night (USD)
Expedia
From $359 per night (USD)
VRBO
Two Bedroom Island Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Forget your worries in this spacious, modern, and serene space. This beautiful and exclusive property is located in a 2 ...
From $359 per night (USD)
VRBO
From $67 per night (USD)
Expedia
Villa on the Ridge
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Modern 4 bedroom villa located within an exclusive 24 hour gated community. Centrally located within 15 minutes of Ocho ...
From $67 per night (USD)
Expedia
From $890 per night (USD)
VRBO
Serai's Island Villa
Bedrooms:
6
Bathrooms:
6
Sleeps:
10
This beautiful and exclusive property is located in a 24 hour gated community with an ocean view. This villa is located ...
From $890 per night (USD)
VRBO
From $242 per night (USD)
Expedia
3-bedroom townhome in amazing Ocho Rios with Pool access, Private Gazebo,Balcony
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Located in Ocho Rios, enjoy what this 3-bedroom townhome has to offer. This superb property features 1 king bed and 2 qu ...
From $242 per night (USD)
Expedia
From $232 per night (USD)
VRBO
Charming 3-bedroom house with AC, WiFi in wonderful Tower Isle
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in the tranquil, gated community of Battle Site—the historic location of the final clash between the British and ...
From $232 per night (USD)
VRBO
From $1250 per night (USD)
Expedia
Private Luxury Oceanview 8BR/8BA Villa/Wi-Fi/Jacuzzi/Backyard BBQ/Gym/Staff/AC
Bedrooms:
8
Bathrooms:
8
Sleeps:
18
Welcome to Adina Villa Your private sanctuary on Jamaica’s North Coast Adina Villa is more than just a place to stay—i ...
From $1250 per night (USD)
Expedia
From $1196 per night (USD)
VRBO
Adina View: Oceanview 8BR, Pool, Jacuzzi, Chef, Gym, WiFi, AC, Backyard BBQ
Bedrooms:
7
Bathrooms:
8
Sleeps:
18
Welcome to Adina Your private sanctuary on Jamaica’s North Coast Adina is more than just a place to stay. It’s a luxur ...
From $1196 per night (USD)
VRBO
From $140 per night (USD)
Expedia
The Rumpanion
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Rumpanion, your perfect getaway in St. Ann! Our 2-bedroom, 2-bathroom home is designed for comfort and re ...
From $140 per night (USD)
Expedia
From $948 per night (USD)
VRBO
Spacious 6-bedroom house with WiFi and AC in charming St. Mary Parish
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Your home away from home in St. Mary Parish with 6 brilliant bedrooms, including 2 queen beds and 4 king beds. This quai ...
From $948 per night (USD)
VRBO
From $570 per night (USD)
Expedia
Luxury Farm House Villa at The Cedars Estate
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
The Cedars Estate –Love Grows Here The Cedars Estate is a historic 100+ acre farm and vintage Great House thoughtfully ...
From $570 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Modern Island Escape w/ Pool, Gym & Patio
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
🌴 Welcome to Serenity Palms JA – Ocho Rios Your peaceful, stylish retreat in the heart of Ocho Rios. Whether you're rel ...
From $152 per night (USD)
VRBO
From $2799 per night (USD)
Expedia
Panoramic Cliffside Luxe Villa
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Perched on a lush hilltop, the vibrant Caribbean Sea sprawls just beyond this impressive 6 bedroom villa. The sleek inte ...
From $2799 per night (USD)
Expedia
From $3002 per night (USD)
VRBO
Luxury Oceanfront Villa in Tower Isle
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Discover Fortune Villas - Villa De La Vista, a luxurious oceanfront retreat in Tower Isle, St. Mary. Perched on a seasid ...
From $3002 per night (USD)
VRBO
From $384 per night (USD)
Expedia
Coastal Escape in Riviera, Tower Isle~Beach Nearby
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to Paradise on Riviera Blvd in Tower Isle –Your Ideal Getaway in just 10 minutes outside of the bustling tourist ...
From $384 per night (USD)
Expedia
From $2579 per night (USD)
VRBO
Luxury Oceanfront Villa~ Fully Staffed~Pool~Jacuzzi~Movie Theatre
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Vista Royale is a luxurious oasis nestled in a beautiful paradise. Vista Royale is a majestic 6 bedroom villa that redef ...
From $2579 per night (USD)
VRBO
From $365 per night (USD)
Expedia
Island Getaway
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Why be confined to a hotel when you can stay here? This stylish, spacious villa is perfect for group trips, just 15-2 ...
From $365 per night (USD)
Expedia
From $668 per night (USD)
VRBO
Villa on the Ridge
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Modern 4 bedroom villa located within an exclusive 24 hour gated community. Centrally located within 15 minutes of Ocho ...
From $668 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Two Bedroom Island Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Forget your worries in this spacious, modern, and serene space. This beautiful and exclusive property is located in a 2 ...
From $334 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Enjoyable 3-bedroom house with AC in Tower Isle
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to this charming house in Tower Isle. This fabulous property boasts 3 bedrooms, including 2 queen beds and 1 twi ...
From $515 per night (USD)
VRBO
From $690 per night (USD)
VRBO
Vista Del Mar 4 Bedroom by Paradise Listing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This charming house in Mary Parish is an excellent choice for guests looking for a cozy retreat. With 4 bedrooms and 3 b ...
From $690 per night (USD)
VRBO
From $690 per night (USD)
VRBO
Vista Del Mar 4 Bedroom by Paradise Listing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Mary Parish is waiting for you at this 4-bedroom house. Step into this awesome, beautiful, and soothing retreat with 3 b ...
From $690 per night (USD)
VRBO
From $970 per night (USD)
Expedia
Adina View Villa
Bedrooms:
7
Bathrooms:
8
Sleeps:
16
"Experience the epitome of luxury at ADINA Luxe. Nestled in a prime location, Chef & Maid (9 - 5pm except Sabbath) inclu ...
From $970 per night (USD)
Expedia
From $2781 per night (USD)
VRBO
Fortune Villa La Vista By Paradise Listing
Bedrooms:
7
Bathrooms:
6
Sleeps:
13
Villa De La Vista is a spacious 6 Bedroom, 6.5 bathroom, Hot Tub, and Large infinity swimming pool master peace at the e ...
From $2781 per night (USD)
VRBO
From $3305 per night (USD)
Expedia
Tu Vista By Paradise Listing
Bedrooms:
9
Bathrooms:
8
Sleeps:
14
Breakfast every morning is Free and welcome Cocktails are on us. Vista is a unique & Stylish 8 Bedrom 9 Bed 8.5 Bathroom ...
From $3305 per night (USD)
Expedia
From $2086 per night (USD)
VRBO
Heavenly Oasis by Paradise Listing
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Just minutes from the beach and nestled in the exotic hills of Oracabessa, Olive Branch Villa sits on beautifully landsc ...
From $2086 per night (USD)
VRBO

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Saint Mary Rentals

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Results: 363 Rentals