Best Vacation Homes in Winston Waterways
House
8.4(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
Private Pool
Oceanfront
Hot Tub
Fireplace/Heating
US $853/Night
7 Nights - US $5,969
Apartment
10.0(10 Reviews)
1 Bedroom
2 Baths
6 Guests
1130.21 ft²
- Fireplace/Heating
Pool
Parking
Air Conditioner
US $278/Night
7 Nights - US $1,943
Boat Rental
10.0(2 Reviews)
1 Bedroom
1 Bath
Spa- Fireplace/Heating
Balcony/Terrace
View
US $1,100/Night
7 Nights - US $7,698
New
House
4 Bedrooms
5 Baths
10 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,128/Night
7 Nights - US $7,893
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
947.22 ft²
Private Beach- Oceanfront
- Pool
Ocean View
US $300/Night
7 Nights - US $2,100
House
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $152/Night
7 Nights - US $1,067
New
Cottage
1 Bedroom
1 Bath
3 Guests
797 ft²
- Balcony/Terrace
Pet Friendly
Kitchen- Parking
US $135/Night
7 Nights - US $948
Hotel
10.0(1 Review)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $335/Night
7 Nights - US $2,347
Winston Waterways Luxury Rentals
House
8 Bedrooms
8 Baths
16 Guests
2200 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $8,558/Night
7 Nights - US $59,906
House
5 Bedrooms
5 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
US $2,265/Night
7 Nights - US $15,855
House
9.8(38 Reviews)
8 Bedrooms
2 Baths
16 Guests
4000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,981/Night
7 Nights - US $13,866
House
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $1,875/Night
7 Nights - US $13,125
House
10.0(1 Review)
3 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $1,819/Night
7 Nights - US $12,736
House
10.0(24 Reviews)
4 Bedrooms
4 Baths
10 Guests
3100 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,724/Night
7 Nights - US $12,066
Hotel
9.4(63 Reviews)
3 Baths
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,528/Night
7 Nights - US $10,697
House
4 Bedrooms
5 Baths
10 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $1,426/Night
7 Nights - US $9,980
Winston Waterways Pet Friendly Vacation Rentals
House
10.0(106 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $277/Night
7 Nights - US $1,941
Resort
8.5(17 Reviews)
10 Baths
47 Guests
573.71 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Ocean View
US $353/Night
7 Nights - US $2,470
Apartment
9.2(29 Reviews)
1 Bedroom
1 Bath
7 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $532/Night
7 Nights - US $3,723
Cottage
10.0(85 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $241/Night
7 Nights - US $1,687
Resort
8.1(668 Reviews)
11 Baths
34 Guests
293.56 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $256/Night
7 Nights - US $1,790
House
10.0(84 Reviews)
2 Bedrooms
3 Baths
7 Guests
950 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $942/Night
7 Nights - US $6,594
Villa
10.0(81 Reviews)
2 Bedrooms
2 Baths
7 Guests
1000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $480/Night
7 Nights - US $3,358
Condo
10.0(51 Reviews)
2 Bedrooms
2 Baths
8 Guests
1000 ft²
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
US $445/Night
7 Nights - US $3,117
Winston Waterways Large Vacation Homes
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $309/Night
7 Nights - US $2,166
US $737/Night
7 Nights - US $5,159
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $158/Night
7 Nights - US $1,104
US $389/Night
7 Nights - US $2,723
Villa
9.6(152 Reviews)
2 Bedrooms
2 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $232/Night
7 Nights - US $1,625
House
8.0(1 Review)
2 Bedrooms
2 Baths
10 Guests
Child Friendly
US $193/Night
7 Nights - US $1,348
House
2 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $431/Night
7 Nights - US $3,019
House
10.0(112 Reviews)
5 Bedrooms
3 Baths
12 Guests
3600 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,135/Night
7 Nights - US $7,948
Why Choose Rent By Owner for your Winston Waterways Vacation Rental Homes?
What makes our Vacation Rentals special?
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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.
Popular Areas for Winston Waterways Vacation Rentals
Where are the best neighborhoods to stay in Winston Waterways?
When planning your stay in Winston Waterways, Key Largo, Florida, you'll find that this charming neighborhood offers a peaceful and scenic environment perfect for relaxing escapes. Known for its convenient access to waterfront activities and tranquil surroundings, Winston Waterways provides an ideal setting for those seeking an authentic Florida Keys experience. Whether you're looking to unwind by the water or enjoy the local community, this area makes it easy to immerse yourself in the natural beauty and laid-back vibe of Key Largo. Booking your vacation rental here ensures a comfortable and memorable visit to one of the most desirable parts of the Florida Keys.
Largo Gardens
This neighborhood offers a tranquil setting perfect for exploring the natural beauty and serene waterways of the region. It’s an ideal spot to find comfortable vacation rentals that provide easy access to local attractions and outdoor activities.
View 1119+ Rentals in Largo GardensBest Times to Visit Winston Waterways
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, allowing you to enjoy the area’s serene waters and coastal charm at their best during the most favorable seasons.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its peak season with warm, inviting weather that appeals to visitors seeking sunshine and outdoor activities.
Average Temperature Daytime: Highs around 78°F (26°C) - Nighttime: Lows around 65°F (18°C)
Spring (March to May)
Spring marks another busy period, with pleasant temperatures and vibrant scenery attracting travelers looking for outdoor adventures in the region.
Average Temperature Daytime: Highs around 82°F (28°C) - Nighttime: Lows around 70°F (21°C)
Off-Season Highlights
Summer (June to August)
While summer can be busy, particularly early on, it tends to slow down later as the heat intensifies, making it a quieter time to visit here.
Average Temperature Daytime: Highs around 89°F (32°C) - Nighttime: Lows around 75°F (24°C)
Fall (September to November)
In fall, the area sees fewer visitors, offering a peaceful atmosphere and comfortable weather, ideal for those looking to avoid crowds.
Average Temperature Daytime: Highs around 83°F (28°C) - Nighttime: Lows around 72°F (22°C)
Weekly Weather Forecast for Winston Waterways
How to Book Your Winston Waterways 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 Winston Waterways
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 outdoor seating areas perfect for relaxing and dining while soaking in the scenic views of the region.
- Take advantage of private pools available at many properties, offering a refreshing escape in the warm Florida sun.
- Benefit from direct access to waterfront spaces, ideal for boating, fishing, or simply enjoying the tranquil water views.
- Make use of outdoor grilling stations to prepare delicious meals while appreciating the pleasant climate here.
- Relax on spacious patios or decks that provide ample space for outdoor gatherings with family or friends.
- Access lush landscaped gardens or courtyards designed to enhance your outdoor experience in this destination.
- Utilize private docks or kayak launches available at select properties for exploring the surrounding waters at your leisure.
Top Attractions Around Winston Waterways
What attractions are nearby?
In this scenic destination, you can enjoy a variety of water-based activities such as snorkeling, fishing, and boating just moments from your vacation rental, offering an ideal setting to explore the natural beauty and vibrant marine life of the region.
Family Activities
- John Pennekamp Coral Reef State Park: Discover the vibrant underwater world through family-friendly snorkeling and glass-bottom boat tours in this renowned park nearby.
- Florida Keys Dive & Surf: Experience exciting water sports such as paddleboarding and kayaking, perfect for creating unforgettable memories on the water.
- Harry Harris Park: Enjoy a relaxing day at this scenic waterfront park with playgrounds, picnic areas, and calm waters ideal for young children to play safely.
- Everglades Alligator Farm: Take an educational airboat tour through the Everglades to see local wildlife, including alligators and native birds, suitable for the whole family.
Adult Activities
- Deep-Sea Fishing: Experience the thrill of deep-sea fishing in the waters nearby, renowned for offering some of the best angling opportunities in the region.
- Snorkeling and Diving Excursions: Explore vibrant coral reefs and marine life through guided snorkeling and diving tours that highlight the area's stunning underwater scenery.
- Boating and Jet Skiing: Rent a boat or jet ski to navigate the picturesque waterways, providing an exciting way to enjoy the scenic surroundings.
- Sunset Cruises: Embark on relaxing sunset cruises that offer breathtaking views of the sky transforming over the calm waters, perfect for unwinding after a day of adventure.
Winston Waterways Travel Tips
How Can You Make the Most of Your Stay?
- Explore local watersports: Take advantage of the region’s renowned waterways by engaging in activities like kayaking or paddleboarding right from your rental and experiencing the scenic beauty firsthand.
- Visit nearby marine parks: Make time to discover the area's vibrant marine life and coral reefs at accessible marine parks, enriching your stay with memorable underwater adventures.
- Plan outdoor dining experiences: Enjoy the mild climate by choosing accommodations with waterfront views, perfect for relaxing meals that let you savor the fresh ocean air.
- Book in advance during peak season: Secure your preferred vacation rentals early to ensure access to the best accommodations and enjoy a stress-free getaway by the water.
Transportation Options
- Car Rentals: Renting a car here gives you the flexibility to explore the surrounding waters and nearby attractions at your own pace.
- Boat Charters: Experience the region’s waterways firsthand by booking a boat charter, offering a unique way to enjoy the ocean and local marine life.
- Taxi Services: Local taxi services provide convenient transportation options for quick trips around the area and to nearby points of interest.
- Public Transit: Public buses serve the region, offering an economical way to navigate this idyllic destination without a vehicle.
Local Customs Options
- Respect for Marine Life: During your stay, you'll notice that locals value preserving the vibrant marine ecosystem that makes this destination unique.
- Celebrating Local Fishing Traditions: Engaging in or observing fishing practices is a common way to connect with the area's heritage and community spirit.
- Embracing Island Hospitality: Visitors often experience warm welcomes and friendly interactions as part of the region's laid-back lifestyle.
- Environmental Conservation Efforts: Participating in or supporting eco-friendly initiatives reflects the community’s commitment to maintaining the area's natural beauty.
Frequently Asked Questions About Winston Waterways?
1. What are the top vacation rentals in Winston Waterways?
There are a lot of options in Winston Waterways. If you plan on staying in the Winston Waterways area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winston Waterways:
- Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
- Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car
- Key Largo Ocean Shore Villa 2 with pool & boat slip
- Historic Jewel of Key Largo With Two Houses on private two Acres
- Private Bay Front House In Key Largo
- Amazing Sunset View in Key Largo
- Sunset Serenity at Moon Bay! Amazing Waterfront condo with Spectacular Sunsets!
- Beautiful Condo - Moon Bay - Waterfront - Spectacular Views in Key Largo
- 2 bedroom & 25' Boat Dock ~ Waterfront Atlantic Side & PrivateTiki dining, bikes
- Bay Sunsets Free Kayaks/Paddleboard Jacuzzi
2. How many vacation rentals have private pools in Winston Waterways?
There are 139 vacation rentals with private pools near Winston Waterways. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Winston Waterways are best for families?
If you are looking for a family-friendly vacation home in Winston Waterways, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winston Waterways:
4. How many Rentbyowner vacation rentals are available in Winston Waterways?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1012 in the Winston Waterways 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 Winston Waterways.
5. What is the cancellation policy for vacation rentals in Winston Waterways?
Cancellation policies vary depending on the individual property listing. It’s best to review the specific rental’s policy directly on the listing or contact the property owner for detailed information.
6. Are there any fees associated with booking a vacation rental in this area?
Additional fees such as service fees, cleaning charges, or security deposits can apply. You should check the listing details or communicate with the owner to understand all potential costs before confirming your reservation.
7. How do I ensure my reservation is confirmed securely?
Reservations are secured through verified listings, and payment is processed through secure channels. It’s recommended to follow the booking instructions outlined on the property page and confirm your reservation promptly.
8. Can I get help if I encounter issues during my stay or booking process?
Yes, support is available through the platform’s customer service team. You can reach out with questions about your reservation, payment, or any issues during your stay by contacting the support center or the property owner directly.
9. What amenities are typically included with vacation rentals near this region?
Most rentals include basic amenities such as Wi-Fi, kitchen facilities, and parking. For specific features or additional services, review the property listing or contact the owner for detailed information.
Winston Waterways Top Rated Vacation Rentals
House
10.0(205 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $484/Night
7 Nights - US $3,386
Apartment
10.0(115 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $480/Night
7 Nights - US $3,363
Condo
10.0(100 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $343/Night
7 Nights - US $2,400
Condo
10.0(99 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
US $372/Night
7 Nights - US $2,602
Condo
10.0(88 Reviews)
2 Bedrooms
1 Bath
6 Guests
947 ft²
- Oceanfront
- Spa
- Pool
- Ocean View
US $271/Night
7 Nights - US $1,894
Condo
10.0(81 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $262/Night
7 Nights - US $1,831
Condo
10.0(77 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $263/Night
7 Nights - US $1,838
House
10.0(73 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $296/Night
7 Nights - US $2,071
