Hotels in Winston Waterways
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Featured Hotels in Winston Waterways

Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
1.82 mi from Winston Waterways
$389 nightly
The price is $433 total per night
$433 total
Feb 22 - Feb 23
Total with taxes and fees
Reefhouse Resort & Marina features a private beach, a marina, and a full-service spa. You can put free parking to good use if you drive. The 24-hour front desk has multilingual staff ready to assist with concierge services, securing valuables, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include an outdoor pool, a 24-hour gym, and WiFi in public areas.
On private beach
Pool

Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Free Cancellation
Reserve now, pay when you stay
2 mi from Winston Waterways
$253 nightly
The price is $285 total per night
$285 total
Mar 4 - Mar 5
Total with taxes and fees
Guests staying at Waterside Suites & Marina enjoy access to a marina, an outdoor pool, and free WiFi in public areas. Limited parking is available. The 24-hour front desk has staff standing by to help with luggage storage, concierge services, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include free newspapers, a terrace, and laundry facilities.
Pool
Pet friendly

Marina Del Mar Resort and Marina
527 Caribbean Drive Key Largo FL
Free Cancellation
Reserve now, pay when you stay
2.15 mi from Winston Waterways
$220 nightly
The price is $248 total per night
$248 total
Feb 22 - Feb 23
Total with taxes and fees
Guests of Marina Del Mar Resort and Marina enjoy a marina, an outdoor pool, and a gym. If you drive, take advantage of free parking. The front desk has multilingual staff that can help secure valuables, and offer advice about sights and eateries nearby. Additional amenities include free WiFi in public areas, a hot tub, and conference space.
Pool
Hot Tub

Bayside Inn Key Largo
99490 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
2.45 mi from Winston Waterways
$262 nightly
The price is $291 total per night
$291 total
Feb 22 - Feb 23
Total with taxes and fees
Guests of Bayside Inn Key Largo enjoy a private beach, an outdoor pool, and a 24-hour gym. The front desk has multilingual staff on hand 24/7 to help with luggage storage, securing valuables, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a business center, coffee/tea in a common area, and a computer station.
On private beach
Pool

Sunset Cove Beach Resort
MM 99.5 Key Largo FL
2.57 mi from Winston Waterways
$236 nightly
The price is $266 total per night
$266 total
Feb 22 - Feb 23
Total with taxes and fees
At Sunset Cove Beach Resort, guests have access to a private beach, a marina, and free WiFi in public areas. If you plan to drive, free parking is available. The front desk has multilingual staff that can answer questions about the accommodations, services, and more. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include free use of bicycles, free newspapers, and laundry facilities.
On private beach
Breakfast included

The Pelican Key Largo Cottages
99340 Overseas Highway Key Largo FL
Free Cancellation
Reserve now, pay when you stay
2.61 mi from Winston Waterways
$233 nightly
The price is $262 total per night
$262 total
Mar 22 - Mar 23
Total with taxes and fees
At The Pelican Key Largo Cottages, guests have access to a private beach, a marina, and free WiFi in public areas. You can take advantage of free parking if you drive. The front desk has multilingual staff that can help with concierge services and luggage storage. Other amenities at this beach hotel include meeting rooms, a computer station, and free newspapers.
On private beach
Parking included

Playa Largo Resort & Spa, Autograph Collection
97450 Overseas Highway Key Largo FL
Free Cancellation
Reserve now, pay when you stay
4.46 mi from Winston Waterways
$498 nightly
The price is $560 total per night
$560 total
Feb 25 - Feb 26
Total with taxes and fees
Guests of Playa Largo Resort & Spa, Autograph Collection have access to a marina, a full-service spa, and an outdoor pool. Valet parking is offered for USD 39.38 per night. Multilingual staff at the 24-hour front desk can assist with securing valuables, concierge services, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, free WiFi in public areas, and a hot tub.
Pool
Hot Tub

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
5.14 mi from Winston Waterways
$536 nightly
The price is $603 total per night
$603 total
Feb 26 - Feb 27
Total with taxes and fees
Guests of Baker's Cay Resort Key Largo, Curio Collection by Hilton have access to a private beach, 2 outdoor pools, and a gym. Valet parking is available for USD 35 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a hot tub, a conference center, and a 24-hour business center.
On private beach
Pool

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
17.75 mi from Winston Waterways
$373 nightly
The price is $420 total per night
$420 total
Mar 22 - Mar 23
Total with taxes and fees
Chesapeake Beach Resort features a private beach, a marina, and 2 outdoor pools. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and free use of bicycles.
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View all propertiesLowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Winston Waterways hotels essential information
Accommodation | 2,300 hotels |
|---|---|
Lowest Price | $248 |
Highest Price | $603 |
Popular hotels | Reefhouse Resort & Marina, Chesapeake Beach Resort, Marina Del Mar Resort and Marina, Bayside Inn Key Largo, Waterside Suites & Marina, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Playa Largo Resort & Spa, Autograph Collection, The Pelican Key Largo Cottages, Sunset Cove Beach Resort |
Recent Reviews

Bayside Inn Key Largo
5/5 Excellent
"Clean room, good location. Lovely pool and beach access "
A verified traveler stayed at Bayside Inn Key Largo
Posted 1 day ago
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