Hotels in Winston Waterways
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Where to stay in Winston Waterways?
9.4 out of 10, Exceptional, (294)
9.4/10
Exceptional
(294)
The price is $238
$238
$334 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hampton Inn Key Largo Manatee Bay
Hampton Inn Key Largo Manatee Bay2.5 star property
0.6 km from Winston Waterways
8.8 out of 10, Excellent, (1003)
8.8/10
Excellent
(1003)
The price is $179
$179
$201 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Marina Del Mar Resort and Marina
Marina Del Mar Resort and Marina2.5 star property
3.5 km from Winston Waterways
8.4 out of 10, Very Good, (1655)
8.4/10
Very Good
(1655)
The price is $129
$129
$173 total
includes taxes & fees
Dec 21 - Dec 22
9.0 out of 10, Wonderful, (1163)
9.0/10
Wonderful
(1163)
The price is $151
$151
$198 total
includes taxes & fees
Dec 20 - Dec 21
9.6 out of 10, Exceptional, (468)
9.6/10
Exceptional
(468)
The price is $219
$219
$275 total
includes taxes & fees
Dec 21 - Dec 22
6.6 out of 10, (1001)
6.6/10
(1001)
The price is $149
$149
$168 total
includes taxes & fees
Dec 20 - Dec 21
9.2 out of 10, Wonderful, (1000)
9.2/10
Wonderful
(1000)
The price is $157
$157
$204 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Pelican Key Largo Cottages
The Pelican Key Largo Cottages2.0 star property
4.2 km from Winston Waterways
8.8 out of 10, Excellent, (1002)
8.8/10
Excellent
(1002)
The price is $122
$122
$137 total
includes taxes & fees
Dec 22 - Dec 23
Holiday Inn Key Largo by IHG
Holiday Inn Key Largo by IHG3.0 star property
3.6 km from Winston Waterways
8.6 out of 10, Excellent, (1014)
8.6/10
Excellent
(1014)
The price is $179
$179
$201 total
includes taxes & fees
Dec 21 - Dec 22
8.6 out of 10, Excellent, (1625)
8.6/10
Excellent
(1625)
The price is $164
$164
$210 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.0 out of 10, Wonderful, (799)
9.0/10
Wonderful
(799)
The price is $219
$219
$246 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Premium Floating Bungalow by Stay Ombi
Premium Floating Bungalow by Stay Ombi3.5 star property
2.4 km from Winston Waterways
The price is $1,259
$1,259
$1,417 total
includes taxes & fees
Jan 1 - Jan 2, 2026
9.2 out of 10, Wonderful, (1329)
9.2/10
Wonderful
(1329)
The price is $229
$229
$298 total
includes taxes & fees
Dec 21 - Dec 22
9.4 out of 10, Exceptional, (133)
9.4/10
Exceptional
(133)
The price is $114
$114
$143 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott Key Largo
Courtyard by Marriott Key Largo3.0 star property
3.4 km from Winston Waterways
8.2 out of 10, Very Good, (1000)
8.2/10
Very Good
(1000)
The price is $197
$197
$222 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.0 out of 10, Wonderful, (1001)
9.0/10
Wonderful
(1001)
The price is $221
$221
$249 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.2 out of 10, Wonderful, (1068)
9.2/10
Wonderful
(1068)
The price is $175
$175
$197 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Kona Kai Resort and Gallery - Adults Only
Kona Kai Resort and Gallery - Adults Only2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.8 out of 10, Exceptional, (294)
9.8/10
Exceptional
(294)
The price is $229
$229
$286 total
includes taxes & fees
Dec 21 - Dec 22
8.8 out of 10, Excellent, (125)
8.8/10
Excellent
(125)
The price is $349
$349
$393 total
includes taxes & fees
Dec 23 - Dec 24
Anchorage Resort & Yacht Club
Anchorage Resort & Yacht Club3.0 star property
7.8 km from Winston Waterways
8.6 out of 10, Excellent, (297)
8.6/10
Excellent
(297)
The price is $250
$250
$281 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Lowest 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.
Lowest 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.
When is the best time to visit Key Largo?
When is the best time to visit Key Largo?Our prices for hotels in Key Largo are cheapest in October
When is the best time to visit Key Largo?
When is the best time to visit Key Largo?
Our prices for hotels in Key Largo are cheapest in October
Price trends for hotels in Key Largo
Pricing is based on two traveler single night rates
Currently viewing crowd sizes and weather for December.
Typical weather for Key Largo
December
Moderate crowds
High 24°C / low 21°C. Sunny most days.
View properties in December 24°
December, Moderate crowds, average high temperature 24 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
23°
January, Moderate crowds, average high temperature 23 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
23°
February, High crowds, average high temperature 23 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
24°
March, High crowds, average high temperature 24 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
26°
April, High crowds, average high temperature 26 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
24°
27°
May, Moderate crowds, average high temperature 27 degrees Celsius, average low temperature 25 degrees Celsius. Sunny most days.
25°
29°
June, Low crowds, average high temperature 29 degrees Celsius, average low temperature 27 degrees Celsius. Sunny most days.
27°
30°
July, High crowds, average high temperature 30 degrees Celsius, average low temperature 28 degrees Celsius. Sunny most days.
28°
30°
August, Moderate crowds, average high temperature 30 degrees Celsius, average low temperature 28 degrees Celsius. Sunny most days.
28°
29°
September, Low crowds, average high temperature 29 degrees Celsius, average low temperature 28 degrees Celsius. Sunny most days.
28°
28°
October, Low crowds, average high temperature 28 degrees Celsius, average low temperature 26 degrees Celsius. Sunny most days.
26°
26°
November, Low crowds, average high temperature 26 degrees Celsius, average low temperature 23 degrees Celsius. Sunny most days.
23°
Monthly weather averages (˚C)
Check out reviews of Winston Waterways hotels guests love
Waterside Suites & Marina
10/10 Excellent
"Beautiful place that's off the beaten path. Can't wait to come back for a longer stay. "
Baker's Cay Resort Key Largo, Curio Collection by Hilton
10/10 Excellent
"Beautiful Hotel and Calusa Restaurant was outstanding "
Holiday Inn Key Largo by IHG
10/10 Excellent
"Amenities and staff were excellent. The overall feel of the resort was just what we weee looking for. "
Bayside Inn Key Largo
10/10 Excellent
"The room was clean, the location is directly next to Snooks, an amazing restaurant/bar, and TJ, at Bayside, is friendly, knowledgeable, and kind. This was our second stay here and we'll be back!"
Marina Del Mar Resort and Marina
10/10 Excellent
"Clean room very nice environment.breakfast no good the muffins were very hard like a rock "
Chesapeake Beach Resort
10/10 Excellent
"Idyllic beautiful beach setting, clean comfortable rooms, lovely setting. "
Playa Largo Resort & Spa, Autograph Collection
10/10 Excellent
"Yes"
Hampton Inn Key Largo Manatee Bay
10/10 Excellent
"Clean hotel, convenient location. Nice little beach area with tiki bar. Room was nice. "
Drift Hotel
10/10 Excellent
"Very nice Hotel/motel reminiscent of what I imagine the old Florida Keys were like.
Lovely beach, dock, and environs."
Find out more about Winston Waterways