Title: Windley Key Condominium Resort Rental from CA $148 | Expedia.ca

 

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![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find and Compare Windley Key Condo Resort Rentals

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## Check prices for these dates

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Windley Key Condo Resorts

No exact matches found, but these alternatives could be just right

## Recommended hotels in Windley Key

![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach/ocean view](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/449b99c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9e08c794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/7c261d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Islamorada

8.2/10

Very good

(1010)

"Great experience, highly recommend staying at the Fisher Inn."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Eduardo

CA $104

CA $164 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information)

![Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oceanfront King Suite w/ Kitchen & Private Balcony | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/42d378ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/29680b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oceanfront King Suite w/ Kitchen & Private Balcony](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/d0b4fd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Drop Anchor

8.8/10

Excellent

(1003)

"Beautiful property and the staff was amazing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John

CA $208

CA $284 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information)

![Classic Room, Patio, Garden View | Terrace/patio](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/224c2448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Room, Patio, Garden View](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/5f27ae80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/01400ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Room, Patio, Garden View | Bathroom](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/3fea31a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ocean View Inn & Pub

9.6/10

Exceptional

(7)

"Awesome place to stay, restaurant and bar attached, outside bar and dining area overlooking the bay. Pool also very nice. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rick

CA $222

CA $249 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Islamorada-Hotels-The-Ocean-View-Inn-Pub.h110683445.Hotel-Information)

![Private beach, sun loungers, beach towels, scuba diving](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4dfe75fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 outdoor pools, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/8de2bfdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/c5948ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Resort in Islamorada

9.0/10

Wonderful

(111)

"Beautiful place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jonathan

CA $286

CA $416 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/be3c8b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/b10fe59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor wedding area](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/ca67d5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coconut Cove Resort and Marina

9.0/10

Wonderful

(141)

"Quiet and relaxing. Great place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Edward

CA $189

CA $213 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information)

![Sundeck](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/9bcc8c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, beach towels, kayaking](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/528adcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Cabin, 1 King Bed, Bay View](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/w1498h1001x2y0-11d0c529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rock Reef Resort

9.2/10

Wonderful

(1065)

"Everything was perfect. Very clean great staff beautiful place to relax ."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Miguel

CA $131

CA $148 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information)

![On the beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/f3e504e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/1508fc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/70c7ac71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/0065f64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Drift Hotel

9.0/10

Wonderful

(1005)

"Very nice place enjoyed myself to the fullest"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

BOBBY ROBERTSON

CA $127

CA $159 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.Hotel-Information)

![Room, 1 King Bed, Bay View | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/66659102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden view](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/d369153c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/c604580a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Key Largo Manatee Bay

8.8/10

Excellent

(1017)

"Great resort"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

david

CA $157

CA $176 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information)

![On the beach, kayaking](https://images.trvl-media.com/lodging/4000000/3920000/3911700/3911616/b6383084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aquamarina Deluxe Sea View Suite | Living area](https://images.trvl-media.com/lodging/4000000/3920000/3911700/3911616/9f59701c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor wedding area](https://images.trvl-media.com/lodging/4000000/3920000/3911700/3911616/9f8e24a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Celeste Deluxe Sea View Suite  | Living area](https://images.trvl-media.com/lodging/4000000/3920000/3911700/3911616/b9dfb26d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Azul del Mar

9.0/10

Wonderful

(784)

"Room was spotless and staff was more than accommodating!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Windy

CA $137

CA $154 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Key-Largo-Hotels-Azul-Del-Mar.h3911616.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/4ac8a422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach umbrellas, beach towels, kayaking](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/ac9979c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/eec761cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/aed267ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dove Creek Resort & Marina, Trademark Collection by Wyndham

7.6/10

Good

(1002)

"clean room nice balcony view nice staff nice breakfast"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Manuel

CA $142

CA $205 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/de0ac7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/9d3b800e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio Suite | Private kitchen](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/0f203959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterside Suites & Marina

9.0/10

Wonderful

(1126)

"Great place to stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chad

CA $155

CA $215 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/e12ff0a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/38a88171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool, open 9 AM to 9 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/b15145a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/e0609cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amoray Dive Resort

9.2/10

Wonderful

(1008)

"Great service, spotless room, and the sunsets!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Peter

CA $137

CA $154 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Key-Largo-Hotels-Amoray-Resort.h5311313.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/9a9545cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/19311fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/af88a0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Marina Del Mar Resort and Marina

8.4/10

Very good

(1634)

"Great location and laid back vibe!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert

CA $129

CA $185 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/b5cef261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor wedding area](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/9192d0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, kayaking, rowing, fishing](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/a2a4b9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Pelican Key Largo Cottages

8.8/10

Excellent

(1010)

"We were delighted with everything The Pelican said it was. The staff was friendly and courteous throughout the property. THE VIEWS were stunning! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ramiro

CA $155

CA $174 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/2a78a3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/3dad51c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/cb9ea3a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/e8b845d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Seafarer Key Largo

9.4/10

Exceptional

(126)

"Everything was especially clean and the breakfast was incredible "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

FATIMA

CA $145

CA $184 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-Largo-Hotels-Seafarer-Key-Largo.h111555855.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/46aade65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier One Bedroom Waterfront Suite Bayview with Sofabed](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/dd3dbaaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/8e763282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bayside Inn Key Largo

8.6/10

Excellent

(1610)

"Great location and helpful staff !"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nikki

CA $165

CA $221 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/fcd75612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite | Living area](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/4ae3e8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/396da292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/3c8fb00e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kona Kai Resort and Gallery - Adults Only

9.8/10

Exceptional

(287)

"The Kona Kai Resort was perfect for us. We especially appreciated the small resort with quiet spaces to relax, read and admire the view. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bastianella

CA $315

CA $394 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Key-Largo-Hotels-Kona-Kai-Resort-And-Gallery.h74501641.Hotel-Information)

![Water view](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Two Queen Beds Water View](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/d6bb28b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fishing](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/371bf8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/d461c69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Tavernier

8.0/10

Very good

(1006)

"Awesome staff. Awesòme place!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David

CA $177

CA $199 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information)

![Private beach, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/fa9b6bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/12d77a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chesapeake Beach Resort

9.2/10

Wonderful

(1582)

"Great breakfast very well kept grounds"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James

CA $196

CA $300 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/d330cb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/31d6a642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 2 Queen Beds, Kitchenette, Bay View](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/c0d44f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Jolla Resort

9.0/10

Wonderful

(1003)

"Great place to stay lovely staff Easy to find "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

diane

CA $98

CA $150 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-07&endDate=2025-12-08&regionId=553248635976197663&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=HOUSE_BOAT)

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## Top Windley Key Hotel Reviews

![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg)

### Fisher Inn Resort & Marina

10/10 Excellent

"Great"

[](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information)

![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg)

### Reefhouse Resort & Marina

10/10 Excellent

"Everything!"

[](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information)

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg)

### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent

"Beautiful room, stunning views "

[](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information)

![The Pelican Key Largo Cottages](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg)

### The Pelican Key Largo Cottages

10/10 Excellent

"My husband and I stayed there for a night. The receptionist was very inviting and friendly. The room was clean and the atmosphere was pleasant being in walking distance from the ocean. "

[](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information)

![Playa Largo Resort & Spa, Autograph Collection](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg)

### Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"This resort has it all. I will go back."

[](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information)

![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg)

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

10/10 Excellent

"As always great staff and amenities. I go there as often as I can , always love it. This time it was off season and they upgraded me to an ocean view for my birthday! 😊"

[](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information)

![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg)

### Coconut Cove Resort and Marina

10/10 Excellent

"Quiet and relaxing. Great place"

[](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information)

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg)

### Creekside Inn

10/10 Excellent

"Awesome staff. Awesòme place!!!"

[](https://expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information)

![Holiday Inn Key Largo by IHG](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg)

### Holiday Inn Key Largo by IHG

10/10 Excellent

"I’ve stayed here on multiple dive trips and I’ve never been disappointed. Right next door to Divers Direct. "

[](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information)

## Find out more about Windley Key

## Windley Key Condo Resorts information

| Number of reviews | 17,492 |
| --- | --- |
| Accommodation | 1 Condo Resorts |
| Lowest Price | CA $148 |
| Highest Price | CA $416 |

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-   [Townhomes in Tavernier](https://www.expedia.ca/Tavernier-Townhomes.d10047-aaTownhomes.Travel-Guide-Accommodation)
-   [Vacation Homes in Upper Matecumbe Key](https://www.expedia.ca/Upper-Matecumbe-Key-Private-Vacation-Homes.d553248635975749648-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Resorts in Upper Matecumbe Key](https://www.expedia.ca/Upper-Matecumbe-Key-Resort-Hotels.d553248635975749648-aaResortHotels.Travel-Guide-Accommodation)
-   [Beach Hotel Hotels in Venetian Shores](https://www.expedia.ca/Venetian-Shores-Islamorada-Hotels-Beach-Hotel.0-n553248635976470270-0-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Airport Shuttle in Venetian Shores](https://www.expedia.ca/Venetian-Shores-Islamorada-Hotels-Hotels-With-Free-Airport-Shuttle.0-n553248635976470270-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
-   [Scuba Diving Hotels in Venetian Shores](https://www.expedia.ca/Venetian-Shores-Islamorada-Hotels-Scuba-Diving-Vacations.0-n553248635976470270-0-tscubadivingvacations.Travel-Guide-Filter-Hotels)
-   [Venetian Shores Hotels](https://www.expedia.ca/Venetian-Shores-Islamorada-Hotels.0-n553248635976470270-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Windley Key Fossil Reef Geological State Park](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Hotels.0-l6282211-0.Travel-Guide-Filter-Hotels)

-   [History of Diving Museum](https://www.expedia.ca/History-Of-Diving-Museum-Matecumbe.d6069257.Vacation-Attraction)
-   [Visit Seabreeze Trailer Park](https://www.expedia.ca/Islamorada-Seabreeze-Trailer-Park.dx553248635976480972)
-   [Visit Venetian Shores](https://www.expedia.ca/Islamorada-Venetian-Shores.dx553248635976470270)
-   [Visit Plantation Key](https://www.expedia.ca/Plantation-Key.dx553248635083898347)
-   [Windley Key Fossil Reef Geological State Park](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)

-   [Avis Rental Cars in Plantation Key](https://www.expedia.ca/Avis-Car-Rentals-In-Plantation-Key.d553248635083898347-c41.Car-Rental-Guide-Suppliers)
-   [Mex Rent A Car Rental Cars in Plantation Key](https://www.expedia.ca/Mex-Rent-A-Car-Car-Rentals-In-Plantation-Key.d553248635083898347-c1084.Car-Rental-Guide-Suppliers)
-   [Pickup Car Rentals in Plantation Key](https://www.expedia.ca/Pickup-Car-Rentals-In-Plantation-Key.d553248635083898347-tPickup.Car-Rental-Guide-Class)

-   [Book Condo Resorts in Windley Key on Expedia.com](https://www.expedia.com/Windley-Key-Condominium-Resort.d553248635976197663-aaCondominiumResort.Travel-Guide-Accommodation)