Vacation Rentals in Winston Waterways, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  Florida
  5.  Key Largo
  6.  Winston Waterways

Refine your search

Price per night

Amenity Filter

Rating

870 Best Vacation Rentals in Winston Waterways (Starting from $113)

Islander Retreat
Islander Retreat
House
Key Largo, FL, USA
0.1k from Winston Waterways center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$287
Average price / night
Check Availability
Seaside Serenity: Your Ultimate Getaway Awaits in Key Largo
Seaside Serenity: Your Ultimate Getaway Awaits in Key Largo
House
Key Largo, FL, 33037, United States
0.0k from Winston Waterways center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms14 Guests
New to Booking
$1285
Average price / night
Check Availability
Corner Kay
Corner Kay
House
Key Largo, FL, USA
1.4k from Winston Waterways center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms10 Guests
New to Booking
$251
Average price / night
Check Availability
Waterfront home with amazing views, boat dock, screened porch & water sport gear
Waterfront home with amazing views, boat dock, screened porch & water sport gear
House
Key Largo, FL, 33037, United States
0.1k from Winston Waterways center

3 Bedrooms8 Guests
New to Booking
$283
Average price / night
Check Availability
Bay Therapy
Bay Therapy
House
Key Largo, FL, USA
1.5k from Winston Waterways center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

3 Bedrooms8 Guests
New to Booking
$583
Average price / night
Check Availability
%OFF LUXURY HOME, WATERFRONT, 5 MINS FROM OCEAN, 80FT DOCK, HOT TUB
%OFF LUXURY HOME, WATERFRONT, 5 MINS FROM OCEAN, 80FT DOCK, HOT TUB
House
Key Largo, FL, 33037, United States
0.1k from Winston Waterways center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

49 reviews

$428
Average price / night
Check Availability
Key Largo Home with Dock and Private Beach Access
Key Largo Home with Dock and Private Beach Access
House
Key Largo, FL, USA
1.5k from Winston Waterways center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Beach

3 Bedrooms8 Guests
New to Booking
$232
Average price / night
Check Availability
New oceanside Florida Keys canal home with pool minutes from the ocean Key Largo
New oceanside Florida Keys canal home with pool minutes from the ocean Key Largo
House
Key Largo, FL, 33037, United States
0.1k from Winston Waterways center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$174
Average price / night
Check Availability
White Palm
White Palm
House
Key Largo, FL, USA
1.6k from Winston Waterways center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$113
Average price / night
Check Availability
Spacious 4-bedroom vacation home minutes to John Pennekamp Coral Reef State Park
Spacious 4-bedroom vacation home minutes to John Pennekamp Coral Reef State Park
House
Key Largo, FL, 33037, United States
0.2k from Winston Waterways center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$803
Average price / night
Check Availability
Canal-Front Key Largo Retreat with Community Beach!
Canal-Front Key Largo Retreat with Community Beach!
House
Key Largo, FL, USA
1.8k from Winston Waterways center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$300
Average price / night
Check Availability
Keys Harbor 20% OFF: Waterfront, Private Boat Dock, Outdoor Oasis
Keys Harbor 20% OFF: Waterfront, Private Boat Dock, Outdoor Oasis
House
Key Largo, FL, 33037, United States
0.2k from Winston Waterways center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
New to Booking
$286
Average price / night
Check Availability
Little slice of heaven right in key largo
Little slice of heaven right in key largo
Apartment
Key Largo, FL, USA
2.0k from Winston Waterways center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom6 Guests
8.9

Fabulous

11 reviews

$175
Average price / night
Check Availability
NEW & BEAUTIFUL HOME WATERFRONT WITH HEATED POOL AND FULL OUTDOOR KITCHEN
NEW & BEAUTIFUL HOME WATERFRONT WITH HEATED POOL AND FULL OUTDOOR KITCHEN
House
Key Largo, FL, 33037, United States
0.2k from Winston Waterways center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$451
Average price / night
Check Availability
350A Waterfront Oasis with hot tub
350A Waterfront Oasis with hot tub
Apartment
Key Largo, FL, USA
2.0k from Winston Waterways center

Apartments, Accommodations, Pet-friendly, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$296
Average price / night
Check Availability
Paradise on the Canal with Ocean Access including Pool & Spa
Paradise on the Canal with Ocean Access including Pool & Spa
House
Key Largo, FL, 33037, United States
0.2k from Winston Waterways center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms8 Guests
8.8

Fabulous

3 reviews

$757
Average price / night
Check Availability
Waterfront Key Largo Oasis with Boat Dock and Swim Spa
Waterfront Key Largo Oasis with Boat Dock and Swim Spa
House
FL, USA
2.0k from Winston Waterways center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

2 Bedrooms5 Guests
New to Booking
$311
Average price / night
Check Availability
Cozy Coastal Villa. Newly renovated private home w/ HEATED pool.
Cozy Coastal Villa. Newly renovated private home w/ HEATED pool.
House
Key Largo, FL, 33037, United States
0.2k from Winston Waterways center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$444
Average price / night
Check Availability
Keys Paradise!
Keys Paradise!
House
Key Largo, FL, USA
2.0k from Winston Waterways center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom6 Guests
9.5

Superb

2 reviews

$198
Average price / night
Check Availability
The Newly Renovated  Couples  Retreat in Key Largo , Pool  beach , and Marina
The Newly Renovated Couples Retreat in Key Largo , Pool beach , and Marina
House
Key Largo, FL, 33037, United States
0.3k from Winston Waterways center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

1 Bedroom4 Guests
10.0

Exceptional

7 reviews

$187
Average price / night
Check Availability
138 RV Vacation Rental in Key Largo Kampground, FL
138 RV Vacation Rental in Key Largo Kampground, FL
House
Key Largo, FL, 33037, United States
0.3k from Winston Waterways center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom5 Guests
10.0

Exceptional

3 reviews

$247
Average price / night
Check Availability
SPECTACULAR HOME IN Key Largo, Florida WITH EXCELLENT VIEWS
SPECTACULAR HOME IN Key Largo, Florida WITH EXCELLENT VIEWS
House
Key Largo, FL, 33037, United States
0.3k from Winston Waterways center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms9 Guests
9.4

Superb

11 reviews

$282
Average price / night
Check Availability
Enjoy the warm sunny Florida Keys with all the extras included @ Arrhouse!
Enjoy the warm sunny Florida Keys with all the extras included @ Arrhouse!
House
Key Largo, FL, 33037, United States
0.3k from Winston Waterways center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms12 Guests
10.0

Exceptional

9 reviews

$287
Average price / night
Check Availability
Cozy RV perfect for a family in tropical Key Largo
Cozy RV perfect for a family in tropical Key Largo
House
Key Largo, FL, 33037, United States
0.4k from Winston Waterways center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$208
Average price / night
Check Availability
Stay in Paradise
Stay in Paradise
House
Key Largo, FL, 33037, United States
0.4k from Winston Waterways center

AC, Dryer, Extra Bed, Internet, Kitchen, Laundry, Washer

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$174
Average price / night
Check Availability
Key Largo Oasis.
Key Largo Oasis.
House
Key Largo, FL, 33037, United States
0.4k from Winston Waterways center

AC, Balcony, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space, Patio

3 Bedrooms4 Guests
New to Booking
$230
Average price / night
Check Availability
Key Largo home with breathtaking water views
Key Largo home with breathtaking water views
House
Key Largo, FL, 33037, United States
0.4k from Winston Waterways center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

2 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$266
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Winston Waterways.

Stay Near Winston Waterways's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Winston Waterways Vacation Rentals on the Map

Frequently Asked Questions

You can explore 870 verified vacation rentals in Winston Waterways. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Winston Waterways vary depending on the season, property size, and location. Rates typically start from around $113 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Winston Waterways include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Winston Waterways welcome pets. Currently, 25 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Winston Waterways often include amenities such as View, Laundry, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.