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Top hotels in Winston Waterways

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$319 nightly
The price is $354 total per night from May 6 to May 7
$354 total
May 6 - May 7
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Family-friendly ...
May kids loved the beach area and staff were very friendly.

Reviewed on May 5, 2026

Opens in a new windowReefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$240 nightly
The price is $270 total per night from May 28 to May 29
$270 total
May 28 - May 29
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
excellent breakfast included. large comfortable rooms

Reviewed on May 5, 2026

Opens in a new windowChesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $164 total per night from May 27 to May 28
$164 total
May 27 - May 28
Total with taxes and fees
A marina and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on ...
We were in a 2 bedroom suite. Thought there was a lounge, but no. So nowhere to sit for 4 except balcony which was ok good view of passing boats .It would have been good if it had been catered for 4 people, ie glasses, cutlery. Kitchen basic but ok, good fridge.

Reviewed on May 4, 2026

Opens in a new windowWaterside Suites & Marina
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2 out of 5
99340 Overseas Highway Key Largo FL
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $159 total per night from May 26 to May 27
$159 total
May 26 - May 27
Total with taxes and fees
This smoke-free hotel's private beach and marina are among the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. ...
Clean and sufficient for our over night stay

Reviewed on May 5, 2026

Opens in a new windowThe Pelican Key Largo Cottages
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

2.5 out of 5
102400 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $152 total per night from May 18 to May 19
$152 total
May 18 - May 19
Total with taxes and fees
A private beach and an outdoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
This is an older hotel. Great beach, bar and breakfast.

Reviewed on May 4, 2026

Opens in a new windowHampton Inn Key Largo Manatee Bay
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$352 nightly
The price is $396 total per night from Jun 2 to Jun 3
$396 total
Jun 2 - Jun 3
Total with taxes and fees
A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
Love it 😍!!! Will come back!

Reviewed on May 5, 2026

Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2 out of 5
527 Caribbean Drive Key Largo FL
$150 nightly
The price is $169 total per night from May 13 to May 14
$169 total
May 13 - May 14
Total with taxes and fees
A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. You'll ...
The property was very clean, comfortable; excellent to enjoy a beautiful and amarizing view, and the staff is really supportive. The front desk ckerk Angie, was really attentive. I am recommend this place for those who hate crowded and noisy places. For sure, I plan to return for another enjoyable ...

Reviewed on May 5, 2026

Opens in a new windowMarina Del Mar Resort and Marina
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $181 total per night from May 6 to May 7
$181 total
May 6 - May 7
Total with taxes and fees
A private beach, a 24-hour gym, and a restaurant are all featured at this hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Enjoy the outdoor ...
It was very good, I will come back for dure

Reviewed on May 5, 2026

Opens in a new windowBayside Inn Key Largo
Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG

3 out of 5
99701 Overseas Hwy Key Largo FL
$170 nightly
The price is $191 total per night from Jun 2 to Jun 3
$191 total
Jun 2 - Jun 3
Total with taxes and fees
A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks ...
Breakfast was delicious, nice staff and great facility.

Reviewed on May 4, 2026

Opens in a new windowHoliday Inn Key Largo by IHG
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Winston Waterways Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Winston Waterways area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Winston Waterways to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Winston Waterways are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Winston Waterways hotel reviews by fellow wanderers