Owner Direct Vacation
Rentals in Winston Waterways

The Best Owner Direct Vacation Rentals in Winston Waterways. Explore thousands of vacation home rentals, large cabins, and villas near Winston Waterways

Explore the Best Winston Waterways Vacation Homes

Looking for the perfect place to stay in Winston Waterways? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Winston Waterways character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos
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10 (3 Reviews)
Apartment
Serenity at Moon Bay!
  • Air Conditioner
  • Parking
  • Pool
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9.1 (172 Reviews)
Resort
Dolphin Point Villas
  • Air Conditioner
  • Parking
  • View
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10 (3 Reviews)
Apartment
Serenity at Moon Bay!
  • Air Conditioner
  • Parking
  • Pool
US
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9.6 (27 Reviews)
Apartment
Key Largo Cottages
  • Air Conditioner
  • Pet Friendly
  • TV
US
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9.6 (27 Reviews)
Apartment
Key Largo Cottages
  • Air Conditioner
  • Pet Friendly
  • TV
US
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9.2 (4 Reviews)
House
Keys Paradise!
  • Air Conditioner
  • Parking
  • Pet Friendly
US
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8.8 (1271 Reviews)
Resort
Reefhouse Resort and Marina
  • Air Conditioner
  • Parking
  • Pet Friendly
US
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Why Travelers Love Using
Owner Direct to
Find Winston Waterways Vacation Rentals

What makes our vacation homes stand out?

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Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

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Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Saturday Jan 24

Winston Waterways, Key Largo

Sat
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20.8°C
Sun
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21.3°C
Mon
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21.1°C
Tue
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16.3°C
Wed
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18.8°C
Thu
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16.8°C
Fri
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19.7°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Winston Waterways vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.

Indoor Amenities

  • indoor-amenities-kitchenFully equipped kitchens
  • indoor-amenities-living-areaSpacious living areas with streaming TVs
  • indoor-amenities-wifiComplimentary Wi-Fi
  • indoor-amenities-acAir conditioning and heating
  • indoor-amenities-washerIn-unit washer and dryer
  • indoor-amenities-bedPlush bedding and comfortable furniture

Outdoor Amenities

  • outdoor-amenities-balconyBalconies or patios with coastal views
  • outdoor-amenities-poolPrivate or shared pools
  • outdoor-amenities-bbqBBQ grills and outdoor dining areas
  • outdoor-amenities-parkingOn-site parking
  • outdoor-amenities-beachEasy access to beaches and attractions

How to Reserve Your Winston Waterways Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

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SEARCH PROPERTIES

Use filters for location, amenities, and budget.

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VIEW DETAILS

Check photos, reviews, and features for your top picks.

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BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

Winston Waterways Vacation Rental FAQs

1. What are the top vacation rentals in Winston Waterways?

2. How many vacation rentals have private pools in Winston Waterways?

There are 130 vacation rentals with private pools near Winston Waterways. Top-rated 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 vacation rentals are available in Winston Waterways?

Currently, the total number of properties listed in 2026 is over 944 in the Winston Waterways area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winston Waterways.