Title: Windley Key Vacation Rentals from $262: Search Short-Term Rentals | Expedia.com

[Windley Key Travel Guide](https://expedia.com/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.com/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Flights to Windley Key](https://expedia.com/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.com/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Car Rentals in Windley Key](https://expedia.com/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[Windley Key Vacation Packages](https://expedia.com/Windley-Key.d553248635976197663.Destination-Travel-Guides)

![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)

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

## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=553248635976197663&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=553248635976197663&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=553248635976197663&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=553248635976197663&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windley Key vacation rentals

![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/b0169681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/13368841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/17a61bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treasure Harbor

[](https://www.expedia.com/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information)

Islamorada

9.0/10

Wonderful

(134 reviews)

"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"

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

Nick

$322 nightly

$362 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information)

![Private beach, sun loungers](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/6213e965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dock](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/235ba8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Cabin | Private kitchen | Coffee/tea maker](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/4fafaddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Cabin | Private kitchen | Coffee/tea maker](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/2ba1466b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kings Kamp

[](https://www.expedia.com/Key-Largo-Hotels-Kings-Kamp.h78323367.Hotel-Information)

Key Largo

8.4/10

Very Good

(30 reviews)

"Clean room, Beautiful view of the sea from the room window."

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

Serhiy

$266 nightly

$299 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-Kings-Kamp.h78323367.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/dd2c750f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/c244835e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![55-inch Smart TV with digital channels, books](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/96d842c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/ab2c2d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premium Floating Bungalow by Stay Ombi

[](https://www.expedia.com/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information)

Key Largo

10/10

Exceptional

(1 review)

$902 nightly

$1,014 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information)

![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fcc01350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/55a08207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Islands of Islamorada

[](https://www.expedia.com/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

Matecumbe

9.8/10

Exceptional

(70 reviews)

"Amazing stay, can’t wait to stay there again!"

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

Anonymous traveler

$948 nightly

$1,067 total

Feb 26 - Feb 27

Total with taxes and fees

[](https://www.expedia.com/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/19240ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Economy Room | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/f0ed1fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach towels](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/4550dbd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Breezy Palms Resort

[](https://www.expedia.com/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

Matecumbe

8.8/10

Excellent

(623 reviews)

"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "

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

Alexander

$232 nightly

$262 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/0ad9df61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/c854d590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/8d386ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/54000000/53650000/53645500/53645406/3a4de8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serenity In The Sun Condo Fabulous Ocean View

[](https://www.expedia.com/Tavernier-Hotels-Serenity-In-The-Sun-Condo-Fabulous-Ocean-View.h53645406.Hotel-Information)

Tavernier

10/10

Exceptional

(110 reviews)

"Fantastic place to stay! Very clean and great hosts. Will stay again. "

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

Les

$500 nightly

$555 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Serenity-In-The-Sun-Condo-Fabulous-Ocean-View.h53645406.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/27000000/26850000/26840200/26840173/w1024h765x0y3-fb83b9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/27000000/26850000/26840200/26840173/w1024h648x0y33-a679fb72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/27000000/26850000/26840200/26840173/w716h768x155y0-db0c2844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/27000000/26850000/26840200/26840173/w1024h648x0y33-65c69fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean view condo with balcony/marina view

[](https://www.expedia.com/Tavernier-Hotels-Ocean-View-Condo-With-Balconymarina-View.h26840173.Hotel-Information)

Tavernier

8.8/10

Excellent

(42 reviews)

"The condo was renovated, and very nicely decorated, very clean and cozy. We enjoyed our short stay. Community and pool were good too. "

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

Lina

$488 nightly

$542 total

Mar 7 - Mar 8

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Ocean-View-Condo-With-Balconymarina-View.h26840173.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/49000000/48450000/48449600/48449553/19054a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/49000000/48450000/48449600/48449553/30c07ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/49000000/48450000/48449600/48449553/8c96c552.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/49000000/48450000/48449600/48449553/9cb7aefd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

[](https://www.expedia.com/Key-Largo-Hotels-Tiny-House2-On-The-Water-Pool.h48449553.Hotel-Information)

Key Largo

9.6/10

Exceptional

(125 reviews)

"We had a wonderful time host was responsive and the property was perfect for our needs"

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

Mike C.

$617 nightly

$685 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-Tiny-House2-On-The-Water-Pool.h48449553.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/43000000/42290000/42281900/42281802/w1052h665x0y34-299237c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/43000000/42290000/42281900/42281802/b09b34f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/43000000/42290000/42281900/42281802/w1052h666x0y34-dd35cbcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42290000/42281900/42281802/f0986046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal comfort in Ocean Pointe Suites. 

[](https://www.expedia.com/Tavernier-Hotels-Warm-Winter-Escape-In-Sunny-Florida-Keys-With-Oceanfront-Private-BeachMarina.h42281802.Hotel-Information)

Tavernier

10/10

Exceptional

(34 reviews)

"Very clean, lots of things to do for the kids on property - large pool and hot tub, tennis and pickle ball courts, and a small beach. "

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

Robert F.

$618 nightly

$686 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Warm-Winter-Escape-In-Sunny-Florida-Keys-With-Oceanfront-Private-BeachMarina.h42281802.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/105000000/104900000/104890400/104890339/7604cab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104900000/104890400/104890339/23d2e5c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/105000000/104900000/104890400/104890339/5ecc1af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104900000/104890400/104890339/f89c793f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flamingo Flats Ocean Pointe 5306 2BR/2BA

[](https://www.expedia.com/Tavernier-Hotels-Marina-View-Ocean-Pointe-5306.h104890339.Hotel-Information)

Tavernier

9.6/10

Exceptional

(7 reviews)

"Great location and prompt support with all questions we had. "

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

Jim I.

$714 nightly

$782 total

Mar 19 - Mar 20

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Marina-View-Ocean-Pointe-5306.h104890339.Hotel-Information)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/106000000/105570000/105563400/105563360/9ed9fba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/106000000/105570000/105563400/105563360/2a4a39d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105570000/105563400/105563360/c0919969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/106000000/105570000/105563400/105563360/954a928d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

[](https://www.expedia.com/Key-Largo-Hotels-Premium-Floating-Bugalow-By-Stay-Ombi-In-The-Keys-With-Stunning-Ocean-Views.h105563360.Hotel-Information)

Key Largo Village

$1,107 nightly

$1,165 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-Premium-Floating-Bugalow-By-Stay-Ombi-In-The-Keys-With-Stunning-Ocean-Views.h105563360.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/28000000/27450000/27440700/27440618/eb6c2974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27440700/27440618/0e4dbd45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27440700/27440618/8a9891f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27450000/27440700/27440618/7f34ca12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LICENSED MGER - MODERN 2/2 OCEANFRONT SUITE! OCEAN & MARINA VIEWS! 2 KING BEDS!

[](https://www.expedia.com/Key-Largo-Hotels-LICENSED-MGER-MODERN-22-OCEANFRONT-SUITE-OCEAN-MARINA-VIEWS-2-KING-BEDS.h27440618.Hotel-Information)

Key Largo

9.6/10

Exceptional

(65 reviews)

"Great location, clean, and comfortable "

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

Christian W.

$722 nightly

$802 total

Mar 13 - Mar 14

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-LICENSED-MGER-MODERN-22-OCEANFRONT-SUITE-OCEAN-MARINA-VIEWS-2-KING-BEDS.h27440618.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/34000000/33500000/33492400/33492389/5addea98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33500000/33492400/33492389/05242623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33500000/33492400/33492389/010f028b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33500000/33492400/33492389/24beca50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sea View Farm Style Ocean front Condo Views

[](https://www.expedia.com/Tavernier-Hotels-Sea-View-Farm-Style-Ocean-Front-Condo-Views.h33492389.Hotel-Information)

Tavernier

10/10

Exceptional

(162 reviews)

"Very clean and quiet location. Beds were comfy and all necessities were provided. Would definately recommend!"

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

Arielle F.

$474 nightly

$527 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Sea-View-Farm-Style-Ocean-Front-Condo-Views.h33492389.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/67000000/66970000/66963900/66963834/d5a56347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66970000/66963900/66963834/bddeba1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/67000000/66970000/66963900/66963834/4ad3d2c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66970000/66963900/66963834/bffe9f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean View Corner Penthouse Ocean Pointe 5416

[](https://www.expedia.com/Tavernier-Hotels-Ocean-View-Corner-Penthouse-Ocean-Pointe-5416.h66963834.Hotel-Information)

Tavernier

9.8/10

Exceptional

(16 reviews)

"Great place, marina and restaurant on site. "

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

Gay M.

$631 nightly

$691 total

Mar 12 - Mar 13

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Ocean-View-Corner-Penthouse-Ocean-Pointe-5416.h66963834.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68220000/68218400/68218360/58925d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/69000000/68220000/68218400/68218360/5114d9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68220000/68218400/68218360/9a6a9f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/69000000/68220000/68218400/68218360/201003ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boho Style Florida Keys Condo Ocean Views

[](https://www.expedia.com/Tavernier-Hotels-Boho-Style-Florida-Keys-Condo-Ocean-Views.h68218360.Hotel-Information)

Tavernier

9.8/10

Exceptional

(46 reviews)

"Would stay there again."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

jamie g.

$502 nightly

$558 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Boho-Style-Florida-Keys-Condo-Ocean-Views.h68218360.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34150000/34143300/34143275/ee01b3bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34143300/34143275/b96653e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34143300/34143275/cdbcc55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/35000000/34150000/34143300/34143275/237e34eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

[](https://www.expedia.com/Key-Largo-Hotels-Casa-Palma-Live-THE-Lavish-Keys-Life-Vibrant.h34143275.Hotel-Information)

Key Largo

9.8/10

Exceptional

(172 reviews)

"Loved this place and will stay again if we go back to the Keys. Gated community with golf cart to go to the pier with great community resources, grills and sitting areas. Favorite part was the lagoon in the middle of the community not far from the screened in back porch. Full of fish you can swim with and calm beach area that is clean and nice with shade when you need it. We didn’t want to leave this place. Highly recommend!!"

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

Chandler G.

$1,277 nightly

$1,417 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-Casa-Palma-Live-THE-Lavish-Keys-Life-Vibrant.h34143275.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256350/9bc23a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256350/079f8926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256350/w1284h942x0y5-9b978d1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256350/5a93ef3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3212 Across from Pool \* King & Queen/Twin Bunk Bed

[](https://www.expedia.com/Tavernier-Hotels-Modern-Coastal-Renovation.h78256350.Hotel-Information)

Tavernier

9.8/10

Exceptional

(152 reviews)

"Great stay lovely home "

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

Yezenia

$442 nightly

$481 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Modern-Coastal-Renovation.h78256350.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/56000000/55470000/55460200/55460149/w1349h897x0y3-bc517a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/56000000/55470000/55460200/55460149/14f4e0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/56000000/55470000/55460200/55460149/w1349h760x0y38-f861809f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/56000000/55470000/55460200/55460149/230eba13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dazzling Ocean Pointe -OP-Main

[](https://www.expedia.com/Tavernier-Hotels-Dazzling-Ocean-View-Suite-Wheated-Pool.h55460149.Hotel-Information)

Tavernier

9.0/10

Wonderful

(90 reviews)

"Great place to stay. Fantastic property grounds. Amazing pool and spa area. Beach is mediocre at best but there are plenty of other beaches around to visit close by. All in all beautiful place to vibe. "

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

Michael H.

[](https://www.expedia.com/Tavernier-Hotels-Dazzling-Ocean-View-Suite-Wheated-Pool.h55460149.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/396e03e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/w1078h802x1y198-a3a83b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/0915fdf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/3bdab314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

[](https://www.expedia.com/Key-Largo-Hotels-Marvelous-2-Bedroom-House-With-AC-In-Key-Largo.h120624610.Hotel-Information)

Key Largo

10/10

Exceptional

(49 reviews)

"Good location. Lagoon and pool right outside door. "

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

Debra C.

$687 nightly

$763 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Key-Largo-Hotels-Marvelous-2-Bedroom-House-With-AC-In-Key-Largo.h120624610.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256364/bc4eb34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256364/f5a9e2a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256364/96107825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256364/52ff82ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lazy Daze Double King Suite Ocean Pointe 2310

[](https://www.expedia.com/Tavernier-Hotels-Lazy-Daze-Double-King-Suite-Ocean-Pointe-2310.h78256364.Hotel-Information)

Tavernier

9.8/10

Exceptional

(26 reviews)

"Everything was exceptionally nice. Would definitely book again."

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

Sharon

$514 nightly

$561 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Tavernier-Hotels-Lazy-Daze-Double-King-Suite-Ocean-Pointe-2310.h78256364.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.com/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09&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.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=CONDO)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=VILLA)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=HOUSE_BOAT)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=COTTAGE)

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## Top Windley Key Hotel Reviews

![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

"Absolutely loved ALL the service and extra attention to detail! Alicia, Maria with cleaning the room, to Kady and Mona with food service and smiles!!! "

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

![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg)

### Waterside Suites & Marina

10/10 Excellent

"Great place to stay, clean, quiet. Recommend!"

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

![Sunset Cove Beach Resort](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/fe271bae_y.jpg)

### Sunset Cove Beach Resort

10/10 Excellent

"Well-manicured, friendly staff. "

[](https://expedia.com/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information)

![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg)

### Drop Anchor

10/10 Excellent

"We were so lucky to find this little hidden gem in Islamorada. We needed a room for 1 night on our way back to Miami, but didn’t need all the frills. Drop Anchor was the perfect place for us. "

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

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg)

### Chesapeake Beach Resort

10/10 Excellent

"Clean room..staff qaa qond"

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

![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg)

### Marina Del Mar Resort and Marina

10/10 Excellent

"Clean room, easy breakfast, and great location for diving."

[](https://expedia.com/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.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

"Staff very friendly and helpful, beach area was amazing and clean. I would suggest not getting a room on the road side as it is very busy and loud. Kayaks were free to use which was also great. The room we had was very small, not much room for unpacking, could use a little more counter space, but good for 2 people, also nice that there was a fridge and microwave in the room. (Included coffee pot and hair dryer as well) walking distance to great restaurants and shopping. "

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg)

### Cheeca Lodge & Spa

10/10 Excellent

"Room was very nice and plenty of room. First time visitor. Tub on the balcony was unexpected bonus"

[](https://expedia.com/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.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

"Excellent stay ! Highly recommend this place. "

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

## Find out more about Windley Key

**Everything you need to know about Windley Key vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windley Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windley Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Windley Key vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Windley Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windley Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $262 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Windley Key rentals**

At Expedia, we put the best Windley Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windley Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windley Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windley Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Windley Key ](https://expedia.com/Windley-Key-Private-Vacation-Homes.d553248635976197663-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Windley Key ](https://expedia.com/Windley-Key-Condos.d553248635976197663-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Windley Key ](https://expedia.com/Windley-Key-Apartments.d553248635976197663-aaApartments.Travel-Guide-Accommodation)
- [Villas in Windley Key ](https://expedia.com/Windley-Key-Villas.d553248635976197663-aaVillas.Travel-Guide-Accommodation)
- [Cottages in Windley Key ](https://expedia.com/Windley-Key-Cottages.d553248635976197663-aaCottages.Travel-Guide-Accommodation)
- [Houseboats in Windley Key ](https://expedia.com/Windley-Key-Houseboats.d553248635976197663-aaHouseboats.Travel-Guide-Accommodation)
- [Aparthotels in Windley Key ](https://expedia.com/Windley-Key-Apart-Hotels.d553248635976197663-aaApartHotels.Travel-Guide-Accommodation)
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- [Cabin Rentals in Windley Key ](https://expedia.com/Windley-Key-Cabins.d553248635976197663-aaCabins.Travel-Guide-Accommodation)
- [Lodges in Windley Key ](https://expedia.com/Windley-Key-Lodges.d553248635976197663-aaLodges.Travel-Guide-Accommodation)
- [Condo Resorts in Windley Key ](https://expedia.com/Windley-Key-Condominium-Resort.d553248635976197663-aaCondominiumResort.Travel-Guide-Accommodation)

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- [Lido Key Beach Hotels](https://expedia.com/Lido-Key-Hotels-Beach-Hotel.0-0-d6138897-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Bahia Honda Key](https://expedia.com/Bahia-Honda-Key-Hotels.d553248635083902001.Travel-Guide-Hotels)
- [Amelia Island Oceanfront Hotels](https://expedia.com/Amelia-Island-Hotels-Oceanfront-Hotels.0-0-d10814-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Amelia Island All-inclusive Resorts](https://expedia.com/Amelia-Island-Hotels-All-Inclusive-Hotel.0-0-d10814-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Amelia Island](https://expedia.com/Amelia-Island-Hotels.d10814.Travel-Guide-Hotels)
- [Hotel Rooms in Stock Island](https://expedia.com/Stock-Island-Hotels.d180166.Travel-Guide-Hotels)
- [Hotel Rooms in Manasota Key](https://expedia.com/Manasota-Key-Hotels.d3000431268.Travel-Guide-Hotels)
- [Hotel Rooms in Sugarloaf Key](https://expedia.com/Sugarloaf-Key-Hotels.d183126.Travel-Guide-Hotels)
- [Florida Keys Brewing Co. hotels](https://expedia.com/Florida-Keys-Brewing-Co-Hotels.0-l553248635997958830-0.Travel-Guide-Filter-Hotels)

Flights

- [Flights to JAX](https://expedia.com/Cheap-Flights-To-Amelia-Island.d10814.Travel-Guide-Flights)

Cars

- [Car rentals in Amelia Island](https://expedia.com/Car-Rentals-In-Amelia-Island.d10814.Car-Rental-Guide)

Activities

- [Things to do in South Tampa](https://expedia.com/Things-To-Do-In-South-Tampa.d6321582.Travel-Guide-Activities)
- [Things to do in Cudjoe Key](https://expedia.com/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities)
- [Things to do in Boca Chica Key](https://expedia.com/Things-To-Do-In-Boca-Chica-Key.d553248635083916609.Travel-Guide-Activities)

Packages

- [Holiday in Amelia Island](https://expedia.com/Amelia-Island.d10814.Destination-Travel-Guides)
- [Sunset Drive Beach](https://expedia.com/Sunset-Drive-Beach-Matecumbe.d672757825479704576.Vacation-Attraction)
- [Anne's Beach](https://expedia.com/Annes-Beach-Matecumbe.d6282204.Vacation-Attraction)

Vacation Rentals

- [Amelia Island Vacation Rental](https://expedia.com/Amelia-Island-Vacation-Rentals.d10814.Travel-Guide-VacationRentals)

General

- [Visit Honeymoon Island State Park](https://expedia.com/Honeymoon-Island-State-Park.dx6160046)
- [Visit Shell Island](https://expedia.com/Shell-Island.dx6312110)
- [Visit Sugarloaf Key](https://expedia.com/Sugarloaf-Key.dx183126)
- [Visit Amelia Island](https://expedia.com/Amelia-Island.dx10814)
- [Visit Upper Matecumbe Key](https://expedia.com/Upper-Matecumbe-Key.dx553248635975749648)