799+ Hotel & Resort Deals in Windley Key |
Windley Key Hotels, Resorts, and Rentals
9.2
Exceptional
(24 Reviews)
- Florida
- Islamorada
- 0.52 mi to center
2401.89 ft²
16 Bathrooms
Free Cancellation
Hotel
- Private Beach
- Oceanfront
- Hot Tub
CA $936/Night
For 7 Nights CA $6,549
9.4
Exceptional
(1014 Reviews)
- Florida
- Islamorada
- 1.23 mi to center
1 Bathroom
Ocean View
Hotel
- Fireplace/Heating
- Pool
- Ocean View
CA $597/Night
For 7 Nights CA $4,179
10.0
Exceptional
(166 Reviews)
- Florida
- Islamorada
- 1.34 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Balcony/Terrace
CA $880/Night
For 7 Nights CA $6,163
9.0
Exceptional
(119 Reviews)
- Florida
- Islamorada
- 1.07 mi to center
480.34 ft²
16 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $793/Night
For 7 Nights CA $5,549
9.4
Exceptional
(430 Reviews)
- Florida
- Islamorada
- 1.06 mi to center
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
CA $766/Night
For 7 Nights CA $5,365
8.8
Fabulous
(853 Reviews)
- Florida
- Islamorada
- 0.95 mi to center
607.39 ft²
20 Bathrooms
Ocean View
Hotel
- Private Beach
- Oceanfront
- Pool
CA $372/Night
For 7 Nights CA $2,606
9.2
Exceptional
(1678 Reviews)
- Florida
- Islamorada
- 0.31 mi to center
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- View
CA $415/Night
For 7 Nights CA $2,902
8.6
Fabulous
(1298 Reviews)
- Florida
- Islamorada
- 1.05 mi to center
346.6 ft²
5 Bathrooms
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- View
CA $258/Night
For 7 Nights CA $1,806
9.2
Exceptional
(1307 Reviews)
- Florida
- Islamorada
- 1.53 mi to center
1 Bathroom
Ocean View
Resort
- Hot Tub
- Spa
- Pool
CA $602/Night
For 7 Nights CA $4,213
5 Star Hotels in Windley Key & Windley Key Luxury Resorts
Over 51+ Luxury Hotels, Resorts, Private Villas, and 5 Star Rentals
8.0
Excellent
(1 Review)
- Florida
- Islamorada
- 1.18 mi to center
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $2,175/Night
For 7 Nights CA $15,224
8.0
Excellent
(1 Review)
- Florida
- Islamorada
- 0.96 mi to center
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $1,115/Night
For 7 Nights CA $7,801
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 1.18 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $1,101/Night
For 7 Nights CA $7,704
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 1.18 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $1,003/Night
For 7 Nights CA $7,020
9.0
Exceptional
(166 Reviews)
- Florida
- Islamorada
- 0.91 mi to center
1 Bathroom
Ocean View
Resort
- Pool
- Ocean View
- Balcony/Terrace
CA $946/Night
For 7 Nights CA $6,622
8.0
Excellent
(1 Review)
- Florida
- Islamorada
- 1.61 mi to center
3 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $898/Night
For 7 Nights CA $6,283
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 0.96 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $859/Night
For 7 Nights CA $6,012
8.0
Excellent
(1 Review)
- Florida
- Islamorada
- 0.96 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $623/Night
For 7 Nights CA $4,362
9.0
Exceptional
(238 Reviews)
- Florida
- Islamorada
- 1.47 mi to center
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
CA $603/Night
For 7 Nights CA $4,220
Best Hotels in Windley Key & Best Resorts
Over 781+ Top-Rated Hotels, Resorts, and Rentals in Windley Key
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 0.63 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
CA $521/Night
For 7 Nights CA $3,646
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 0.96 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
CA $462/Night
For 7 Nights CA $3,234
9.2
Exceptional
(1004 Reviews)
- Florida
- Islamorada
- 1.06 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $366/Night
For 7 Nights CA $2,564
9.2
Exceptional
(22 Reviews)
- Florida
- Islamorada
- 1.35 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Kitchen
CA $457/Night
For 7 Nights CA $3,201
9.2
Exceptional
(10 Reviews)
- Florida
- Islamorada
- 0.96 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $530/Night
For 7 Nights CA $3,711
9.2
Exceptional
(10 Reviews)
- Florida
- Islamorada
- 0.89 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $485/Night
For 7 Nights CA $3,395
9.0
Exceptional
(1005 Reviews)
- Florida
- Islamorada
- 0.96 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Kitchen
CA $347/Night
For 7 Nights CA $2,429
9.0
Exceptional
(2 Reviews)
- Florida
- Islamorada
- 0.63 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $521/Night
For 7 Nights CA $3,646
8.8
Fabulous
(1000 Reviews)
- Florida
- Islamorada
- 1.72 mi to center
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
CA $538/Night
For 7 Nights CA $3,767
Cheap Hotels in Windley Key, Discounts, & Deals
Over 772+ Cheap Windley Key Hotels, Resorts, and Rentals
7.2
Very Good
(642 Reviews)
581.25 ft²
7 Bathrooms
Hotel
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $279/Night
For 7 Nights CA $1,955
7.7
Very Good
(871 Reviews)
- Florida
- Islamorada
- 1.61 mi to center
388.58 ft²
10 Bathrooms
Free Cancellation
Hotel
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $283/Night
For 7 Nights CA $1,984
8.1
Excellent
(125 Reviews)
461.06 ft²
12 Bathrooms
Hotel
- Oceanfront
- Pool
- Ocean View
CA $336/Night
For 7 Nights CA $2,355
8.4
Excellent
(316 Reviews)
- Florida
- Islamorada
- 1.35 mi to center
247.57 ft²
2 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Pool
- Ocean View
CA $339/Night
For 7 Nights CA $2,373
2.0
Average
(1 Review)
- Florida
- Islamorada
- 0.63 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
CA $344/Night
For 7 Nights CA $2,408
New
- Florida
- Islamorada
- 0.63 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
CA $344/Night
For 7 Nights CA $2,408
New
- Florida
- Islamorada
- 0.63 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
CA $344/Night
For 7 Nights CA $2,408
8.2
Excellent
(1009 Reviews)
- Florida
- Islamorada
- 1.61 mi to center
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
CA $378/Night
For 7 Nights CA $2,643
8.0
Excellent
(2 Reviews)
- Florida
- Islamorada
- 0.63 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $383/Night
For 7 Nights CA $2,680
Hotels Near Windley Key & Other Nearby Resorts
Over 763+ Hotels in Windley Key and Other Resorts & Rentals Nearby
8.3
Excellent
(272 Reviews)
- Florida
- Islamorada
- 1.44 mi to center
279.86 ft²
5 Bathrooms
Ocean View
Hotel
- Oceanfront
- Pool
- Ocean View
CA $417/Night
For 7 Nights CA $2,916
7.6
Very Good
(1008 Reviews)
- Florida
- Islamorada
- 0.63 mi to center
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
CA $402/Night
For 7 Nights CA $2,814
10.0
Exceptional
(2 Reviews)
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
House
- Spa
- Pool
- View
CA $1,331/Night
For 7 Nights CA $9,317
9.8
Exceptional
(72 Reviews)
- Florida
- Islamorada
- 0.52 mi to center
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Oceanfront
- Hot Tub
- Spa
CA $1,314/Night
For 7 Nights CA $9,201
9.6
Exceptional
(19 Reviews)
1550 ft²
6 Guests
2 Bedrooms
2 Bathrooms
House
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $551/Night
For 7 Nights CA $3,858
9.6
Exceptional
(242 Reviews)
- Florida
- Islamorada
- 3.22 mi to center
1 Bedroom
1 Bathroom
Ocean View
House
- Pool
- Ocean View
- Balcony/Terrace
CA $347/Night
For 7 Nights CA $2,429
9.5
Exceptional
(2 Reviews)
1302.43 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Villa
- Private Beach
- Oceanfront
- Pool
CA $682/Night
For 7 Nights CA $4,774
9.0
Exceptional
(139 Reviews)
- Florida
- Islamorada
- 3.28 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Boat Rental
- Pool
- Kitchen
- Parking
CA $457/Night
For 7 Nights CA $3,202
9.0
Exceptional
(14 Reviews)
- Florida
- Islamorada
- 1.81 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
CA $632/Night
For 7 Nights CA $4,427
Windley Key Vacation Rentals, Villas, & Hotel Suites
Over 645+ Windley Key Vacation Rentals, Cabins, Cottages, Condos & Holiday Homes
9.1
Exceptional
(136 Reviews)
- Florida
- Islamorada
- 3.20 mi to center
538.19 ft²
39 Guests
12 Bathrooms
Ocean View
Resort
- Oceanfront
- Fireplace/Heating
- Pool
CA $376/Night
For 7 Nights CA $2,636
New
- Florida
- Islamorada
- 1.79 mi to center
1700 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Pool
- Ocean View
- Balcony/Terrace
CA $1,008/Night
For 7 Nights CA $7,053
8.7
Fabulous
(1439 Reviews)
- Florida
- Islamorada
- 1.23 mi to center
436.91 ft²
68 Guests
22 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $979/Night
For 7 Nights CA $6,849
8.6
Fabulous
(862 Reviews)
- Florida
- Islamorada
- 0.31 mi to center
391.64 ft²
75 Guests
19 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $481/Night
For 7 Nights CA $3,366
8.6
Fabulous
(77 Reviews)
- Florida
- Islamorada
- 0.88 mi to center
418.14 ft²
69 Guests
18 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $894/Night
For 7 Nights CA $6,260
8.0
Excellent
(1 Review)
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
House
- Spa
- View
- Breakfast
CA $1,159/Night
For 7 Nights CA $8,111
7.8
Very Good
(361 Reviews)
- Florida
- Islamorada
- 1.70 mi to center
234.85 ft²
43 Guests
11 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $497/Night
For 7 Nights CA $3,480
7.7
Very Good
(3 Reviews)
1582.29 ft²
12 Guests
5 Bedrooms
4 Bathrooms
House
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $248/Night
For 7 Nights CA $1,736
New
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Pool
- View
- Breakfast
CA $1,765/Night
For 7 Nights CA $12,355
Pet Friendly Hotels in Windley Key
Over 275+ Hotels, Inns, Motels, Resorts, & Rentals that Accept Pets
New
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Spa
- Pool
- View
CA $1,105/Night
For 7 Nights CA $7,735
New
1700.7 ft²
7 Guests
3 Bedrooms
3 Bathrooms
House
- Oceanfront
- Pool
- Ocean View
CA $1,053/Night
For 7 Nights CA $7,369
New
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Spa
- Pool
- View
CA $1,015/Night
For 7 Nights CA $7,108
New
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Pool
- View
- Breakfast
CA $850/Night
For 7 Nights CA $5,951
New
18 Guests
6 Bedrooms
6 Bathrooms
House
- Oceanfront
- Spa
- Fireplace/Heating
Unlock the Best Price
New
12 Guests
4 Bedrooms
4 Bathrooms
Apartment
- Oceanfront
- Spa
- Fireplace/Heating
CA $1,514/Night
For 7 Nights CA $10,600
New
12 Guests
4 Bedrooms
3 Bathrooms
House
- Oceanfront
- Spa
- Fireplace/Heating
CA $1,135/Night
For 7 Nights CA $7,947
New
7 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Oceanfront
- Spa
- Fireplace/Heating
CA $758/Night
For 7 Nights CA $5,305
New
6 Guests
1 Bedroom
1 Bathroom
Boat Rental
- Private Beach
- Oceanfront
- Ocean View
CA $471/Night
For 7 Nights CA $3,299
Windley Key Resorts and All Inclusive Hotels
Over 71+ Windley Key All Inclusive Resorts, All Inclusive Hotels, and Full Service Rentals
New
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
House
- Pool
- View
- Breakfast
CA $1,634/Night
For 7 Nights CA $11,439
8.2
Excellent
(1000 Reviews)
- Florida
- Islamorada
- 1.07 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Kitchen
CA $260/Night
For 7 Nights CA $1,822
New
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Pool
- View
- Breakfast
CA $864/Night
For 7 Nights CA $6,047
Last Minute Hotel Deals, Rentals, & Hotels Tonight
Over 165+ Book a Last Minute Hotel in Windley Key and Save 30-50%
New
1280.91 ft²
4 Guests
2 Bedrooms
2 Bathrooms
House
- Oceanfront
- Fireplace/Heating
- Pool
CA $347/Night
For 7 Nights CA $2,431
New
1280.91 ft²
4 Guests
2 Bedrooms
2 Bathrooms
House
- Oceanfront
- Hot Tub
- Spa
CA $284/Night
For 7 Nights CA $1,987
New
- Florida
- Islamorada
- 3.89 mi to center
1345.49 ft²
8 Guests
1 Bedroom
2 Bathrooms
Ocean View
Apartment
- Private Beach
- Fireplace/Heating
- Pool
CA $278/Night
For 7 Nights CA $1,948
New
- Florida
- Islamorada
- 3.85 mi to center
1345.49 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $182/Night
For 7 Nights CA $1,273
New
1280.91 ft²
4 Guests
2 Bedrooms
2 Bathrooms
House
- Oceanfront
- Hot Tub
- Spa
CA $265/Night
For 7 Nights CA $1,852
CA $353/Night
For 7 Nights CA $2,469
CA $284/Night
For 7 Nights CA $1,987
CA $271/Night
For 7 Nights CA $1,900
CA $259/Night
For 7 Nights CA $1,813
Book a Last Minute Place to Stay in Windley Key
About Windley Key Vacation Rentals
There are more than 799 places to stay in Windley Key that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Windley Key.
Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Windley Key, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Windley Key. Places to stay near Windley Key are 660.73 ft² on average, with prices averaging CA $1,121 a night.
Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Windley Key with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.
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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Windley Key
| Type | Count |
|---|---|
| Vacation Homes | 499 |
| Holiday Apartments | 87 |
| Villas | 38 |
| Others | 12 |
| Cottages | 10 |
| Unique Vacation Rentals | 6 |
Use these Quick Filters to Find a Vacation Rental in Windley Key
★ Pro Tip: Hotala.ca has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Windley Key.
Weather in Windley Key, FL
View the weather forecast for Windley Key before booking your Windley Key Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Stay Near Windley Key's Top Attractions
Hotala.ca can help you find hotels, resorts, and rentals near many of Windley Key's top attractions, neighborhoods, and points of interest.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods
Frequently Asked Questions About Windley Key?
What are the top hotels or resorts in Windley Key?
You have a lot of choices in or near Windley Key. If you need a hotel in the Windley Key area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Windley Key:
- The Caribbean Resort
- Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea
- Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed
- The Cove, Age 21 Plus, Junior Suite, 1 King, Ocean view, Balcony
- Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!
- Guest Room, 1 King: Resort w/Marina and 3 Outdoor Pool | Free Parking
- Islander Resort
- Casa Morada
- Chesapeake Beach Resort
- Cheeca Lodge & Spa
Which hotel or resort in Windley Key is best for families?
If you are looking for a family-friendly hotel, resort, or vacation home in Windley Key, check out one of the following places to stay as all are highly-rated accommodation choices with excellent reviews for families or groups staying in Windley Key:
- Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
- Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
- Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
How many hotels, resorts, or rentals are available in Windley Key?
At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2026 is over 799 in the Windley Key area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Windley Key.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Venetian Shores Hotel & Resort Deals in Florida | 41 |
People Also Ask
Finding the best prices in Windley Key
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