Best Vacation Homes in Stewart Town
Villa
10.0(93 Reviews)
3 Bedrooms
3 Baths
6 Guests
2800 ft²
Private Pool
Pool
Ocean View
Balcony/Terrace
US $690/Night
7 Nights - US $4,830
House
10.0(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
Private Beach
Oceanfront- Ocean View
View
US $130/Night
7 Nights - US $910
Villa
10.0(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
Hot Tub
Spa
US $2,250/Night
7 Nights - US $15,750
Villa
10.0(56 Reviews)
4 Bedrooms
4 Baths
10 Guests
5500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,283/Night
7 Nights - US $8,981
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
75.35 ft²
- Private Beach
- Oceanfront
- Ocean View
- Balcony/Terrace
US $135/Night
7 Nights - US $945
Villa
10.0(38 Reviews)
6 Bedrooms
6 Baths
14 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,500/Night
7 Nights - US $10,500
Villa
10.0(31 Reviews)
8 Bedrooms
9 Baths
17 Guests
- Pool
- Balcony/Terrace
Kitchen
Air Conditioner
US $2,686/Night
7 Nights - US $18,805
Villa
10.0(8 Reviews)
5 Bedrooms
7 Baths
10 Guests
20000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $1,758/Night
7 Nights - US $12,306
Stewart Town Luxury Rentals
House
10.0(5 Reviews)
7 Bedrooms
7 Baths
14 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $3,800/Night
7 Nights - US $26,600
House
9.6(44 Reviews)
6 Bedrooms
6 Baths
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $2,383/Night
7 Nights - US $16,681
House
4 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,766/Night
7 Nights - US $12,360
Villa
5 Bedrooms
3 Baths
12 Guests
- Air Conditioner
Internet
Child Friendly
Laundry
US $1,500/Night
7 Nights - US $10,500
US $1,452/Night
7 Nights - US $10,164
Villa
9.4(87 Reviews)
6 Bedrooms
3 Baths
14 Guests
4000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,333/Night
7 Nights - US $9,331
House
9.6(34 Reviews)
5 Bedrooms
5 Baths
12 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,330/Night
7 Nights - US $9,310
Villa
9.8(133 Reviews)
5 Bedrooms
5 Baths
10 Guests
5000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,317/Night
7 Nights - US $9,219
Stewart Town Pet Friendly Vacation Rentals
Villa
6 Bedrooms
6 Baths
14 Guests
2153 ft²
Fireplace/Heating- Balcony/Terrace
Pet Friendly- Kitchen
US $596/Night
7 Nights - US $4,170
House
9.0(1 Review)
4 Bedrooms
2 Baths
4 Guests
645.83 ft²
- Oceanfront
- Spa
- Ocean View
- Balcony/Terrace
US $134/Night
7 Nights - US $936
House
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $201/Night
7 Nights - US $1,409
US $434/Night
7 Nights - US $3,035
House
8.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
134.55 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $53/Night
7 Nights - US $369
US $304/Night
7 Nights - US $2,130
New
House
2 Bedrooms
2 Baths
5 Guests
990 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $245/Night
7 Nights - US $1,714
Villa
3 Bedrooms
3 Baths
8 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $217/Night
7 Nights - US $1,519
Stewart Town Large Vacation Homes
House
10.0(1 Review)
5 Bedrooms
5 Baths
12 Guests
6000 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $1,198/Night
7 Nights - US $8,386
Villa
5 Bedrooms
5 Baths
14 Guests
5597.23 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $558/Night
7 Nights - US $3,909
Villa
8.0(1 Review)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
Parking
US $260/Night
7 Nights - US $1,820
Villa
9.8(33 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,238/Night
7 Nights - US $8,666
Villa
6 Bedrooms
6 Baths
14 Guests
2152.78 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $540/Night
7 Nights - US $3,777
Villa
9.8(17 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $842/Night
7 Nights - US $5,894
Villa
6.0(1 Review)
5 Bedrooms
6 Baths
10 Guests
8500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,080/Night
7 Nights - US $7,560
Villa
5 Bedrooms
6 Baths
10 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,215/Night
7 Nights - US $8,505
Why Choose Rent By Owner for your Stewart Town Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Stewart Town
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the region’s shoulder seasons when the weather is pleasant and attractions are less crowded, ensuring an enjoyable vacation experience in this destination.
Peak Season Highlights
December to April
During these months, you can enjoy warm weather and sunny skies, making it an ideal time to explore the area’s natural beauty and local culture.
Average Temperature Daytime: around 85°F (29°C) - Nighttime: around 70°F (21°C)
July to August
This period offers vibrant local events and lively atmospheres, perfect for experiencing the region’s energetic spirit while enjoying pleasant temperatures.
Average Temperature Daytime: about 88°F (31°C) - Nighttime: around 73°F (23°C)
Off-Season Highlights
May to June
With fewer visitors, this shoulder season provides a more relaxed experience and better deals on vacation rentals in the area.
Average Temperature Daytime: approximately 83°F (28°C) - Nighttime: around 68°F (20°C)
September to November
As the region transitions into wetter months, accommodation prices tend to drop, offering a quieter retreat for those seeking tranquility in the area.
Average Temperature Daytime: roughly 80°F (27°C) - Nighttime: about 65°F (18°C)
Weekly Weather Forecast for Stewart Town
How to Book Your Stewart Town Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Stewart Town
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to relax and unwind during your stay in this region.
- Take advantage of spacious patios or verandas perfect for outdoor dining and socializing.
- Make use of well-maintained gardens that add natural beauty to your outdoor experience.
- Benefit from covered outdoor seating areas ideal for enjoying the warm Caribbean climate.
- Experience the convenience of on-site barbecue grills for outdoor cooking with family or friends.
- Explore nearby walking trails and outdoor recreational spaces to immerse yourself in the area's natural scenery.
- Relax in charming courtyards that provide a peaceful retreat amidst the tropical surroundings.
Top Attractions Around Stewart Town
What attractions are nearby?
In this vibrant area, you can enjoy exploring nearby beaches, indulging in local cuisine, or engaging in water activities that showcase the natural beauty of the region surrounding Stewart Town, Jamaica.
Family Activities
- Historical Site Tours: Discover the rich heritage of this region by exploring local historical sites that offer engaging insights into its past.
- Beach Days: Relax and play on the sandy shores nearby, making the most of the family-friendly beaches perfect for both lounging and water activities.
- Local Market Visits: Experience the vibrant culture by browsing through bustling markets where you can find authentic crafts and fresh regional produce.
- Nature Walks and Trails: Enjoy family-friendly hikes in scenic areas surrounding here, providing opportunities to admire lush scenery and local flora and fauna.
Adult Activities
- Snorkeling and Diving Adventures: Explore the vibrant marine life just off the coast, making it a perfect activity for those staying in the area who want to experience Jamaica’s underwater beauty firsthand.
- Cultural Tours and Historic Sites: Discover the rich history and local culture through guided tours that highlight the area's heritage, giving you an authentic Jamaican experience during your stay.
- Fishing Excursions: Enjoy deep-sea fishing trips where you can catch a variety of local species, ideal for anglers seeking a memorable adventure in this region.
- Relaxing Beach Days: Unwind on pristine beaches with stunning ocean views, offering a tranquil escape for adults looking to soak up the sun and enjoy the peaceful surroundings.
Other Places to Stay in Stewart Town
Saint Andrew Parish
Stewart Town Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Research local attractions and outdoor opportunities around Stewart Town, Jamaica to ensure you make the most of your time here.
- Choose the Right Vacation Rental: Opt for accommodations that offer easy access to the region's natural beauty and cultural sites for a more enriching experience.
- Respect Local Culture: Engage with the community respectfully and learn about the area's traditions to deepen your connection during your stay.
- Stay Safe and Prepared: Familiarize yourself with safety tips specific to the region to enjoy a worry-free visit to this destination in comfort and security.
Transportation Options
- Local Bus Service: An affordable and convenient way to explore the area, connecting you to nearby attractions and neighboring towns in Stewart Town, Jamaica.
- Taxis and Private Transfers: Reliable and comfortable options for direct travel within the region, ensuring a seamless journey from your vacation rental to key destinations.
- Car Rentals: Ideal if you prefer the flexibility to explore at your own pace, with several rental agencies available near Stewart Town for easy access to vehicles.
- Water Taxis or Ferries: Available for scenic transportation along the coast, offering a unique perspective of the surrounding waters and coastline here.
Local Customs Options
- Greetings with Respect: In this destination, it is customary to show respect through polite greetings, often accompanied by a friendly smile, reflecting the warm hospitality of the region.
- Local Music and Dance: Participating in or appreciating traditional music and dance is an important aspect of the area's culture, offering you an authentic experience of local celebrations.
- Sharing Confections and Drinks: When visiting here, sharing food and beverages during social interactions signifies friendship and community spirit, a cherished custom of the region.
- Attire for Religious and Cultural Events: Dressing modestly and respectfully when attending local religious or cultural gatherings demonstrates your appreciation for the community’s traditions.
Stewart Town Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Stewart Town?
There are a lot of options in Stewart Town. If you plan on staying in the Stewart Town area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Stewart Town:
- Seahorse- - A Slice Of Caribbean Paradise On A Private Beach, Gated Community
- SeaEsta at Bengal ; Cool Chic and all Caribbean.
- Villa FANTASY - ON PRIVATE BEACH IN A GATED COMMUNITY
- 8Br, 7Ba, fully staffed Jamaica Villa for rent with Chef and Butler
- An Ultra-Luxurious Resort Style Ocean View Villa. Optional Yacht, Fully Staffed!
- Modern Townhouse with beach/pool access which offers peace, quiet and relaxation
- Osmax Oasis 2 bedrooms near Puerto Seco Beach
- AMANOKA PROMISES A LUXURIOUS AND TRULY ENJOYABLE VACATION.
- Jamaica Coastal Getaway
- Lux Sea View Camelot Village Discovery Bay
2. How many vacation rentals have private pools in Stewart Town?
There are 15 vacation rentals with private pools near Stewart Town. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Stewart Town are best for families?
If you are looking for a family-friendly vacation home in Stewart Town, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Stewart Town:
4. How many Rentbyowner vacation rentals are available in Stewart Town?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 245 in the Stewart Town area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Stewart Town.
5. What is the cancellation policy for vacation rentals in Stewart Town, Jamaica?
The cancellation policy varies by property; please review the specific listing details or contact the owner directly to understand the applicable terms and any potential fees.
6. How do I find available dates and secure my stay at a vacation rental here?
You can check availability and book your preferred dates through the listing page. If you have special requests or need assistance, reaching out to the property owner can ensure a smooth reservation process.
7. Are there any additional fees or charges when booking a vacation rental in this region?
Additional fees such as cleaning, service charges, or security deposits may apply. These are detailed in the listing, or you can ask the owner for clarification before confirming your booking.
8. What amenities are typically included with vacation rentals in this destination?
Most properties offer essential amenities like Wi-Fi, kitchen facilities, and air conditioning. To ensure the property meets your needs, review the listing description carefully or contact the owner for specific details.
9. Is it possible to make special requests or modifications to my booking in the area?
Yes, many owners are willing to accommodate special requests, subject to availability. It's best to communicate your needs directly with the property owner during the booking process.
Stewart Town Top Rated Vacation Rentals
House
10.0(8 Reviews)
2 Bedrooms
3 Baths
4 Guests
1275 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $105/Night
7 Nights - US $733
US $108/Night
7 Nights - US $753
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $72/Night
7 Nights - US $502
House
9.8(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $132/Night
7 Nights - US $922
House
9.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $123/Night
7 Nights - US $861
House
9.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
Breakfast- Parking
US $87/Night
7 Nights - US $609
House
8.6(49 Reviews)
3 Bedrooms
3 Baths
7 Guests
301.39 ft²
- Oceanfront
- Spa
- Pool
- Ocean View
US $89/Night
7 Nights - US $624
Apartment
8.0(1 Review)
3 Bedrooms
4 Baths
6 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $450/Night
7 Nights - US $3,150
