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Vacation Rentals in Windley Key, Florida

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about Windley Key

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Windley Key, Florida vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Windley Key are added and updated every week!

Compared to hotels, Windley Key vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Windley Key, Florida Vacation Rentals and Tourism

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Windley Key things to do

 

Paddle The Florida Keys

I went back once again last weekend because it's the only place with this friendly and cool of a staff! Scott the owner is a great guy! His staff is very...read more

 

History of Diving Museum

On our way to the keys I spotted this place WOW just take your time and look around it's really interesting. Everybody had a good time museum was well put...read more

 

Theater of the Sea

This place rocks. Had a blast with my wife and 2 kids (under 10). Really a great flow to the shows and you are SO close to all the animals. My daughter...read more

 

Conch Republic Divers

I had to change my review since it's been about 8 years since I started diving with Conch Republic. All of the staff is great and helpful. Brenda has a...read more

 

Anne's Beach

Parking is extremely limited as there is only about 8-9 parking spaces available and one must wait for someone else to leave in order to park. Beach itself...read more

 

Robbie's of Islamorada

The rental boats are in need of serious attention. I understand they are rentals and get abused but it should not take 5-15 mins every time you go to start...read more

 

Grouchy Turtle

My boyfriend and I had a great time on a Sunset Cruise with Grouchy Turtle Tours recently! There is nothing like watching the sunset in the keys from the...read more

 

Islamorada Boat Tours

It's moved across Whale Harbor to the Holiday Isle. Great boat and crew that delivered good viz. and a great time. Crew explained what was going on and...read more

 

Florida Keys Dive Center

If you get seasick, this might not be the trip for you. We went out on a snorkeling trip with a huge group of people - all ages, all fitness levels (it was...read more

 

Islamorada Dive Center

I dove with Islamorada Dive Center on 7/28/14. At first I was worried because the boat held so many people, but then discovered there were many guides and...read more

 

Key Dives

8th time back to Key Dives in as many years. What a terrific group. Happy, pleasant, friendly, professional. My (then) 9 year old daughter earned her open...read more

 

Froggys Fitness

Please note this review is done by a competitive powerlifter. I gave this place a 2 star rating. I feel it's a good place if you are just looking to lift on...read more

 

Bud N' Mary's Fishing Marina

Horrific! I booked a trip for a total of 6 people a year in advance. I called every few months to make sure we were still good to go. I had people flying...read more

 

Aquaholic Adventures

We decided to do the night paddleboarding tour and what an experience! I was a little scared and not sure what to expect but Tyler and Casey put my emotions...read more

 

Indian Key State Historic Site

Pretty fun to kayak to. There is no beach but you can check out tiny fish and hermit crabs while 'snorkeling' around the mangroves. Other than that, it's...read more

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Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
Windley Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $2,800 - $4,200 /wk
 
 
 
 
 

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Islamorada – Simply Beautiful w/ Free Wifi, Hi-Def TV, & Many Extras; Top Rated
Windley Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $170 - $225 /nt
    $1,400 - $1,575 /wk
    $3,200 - $4,500 /mth
 
 
 
 
 

12 reviews write a review

*Offer in September!* Anglers Reef Oceanfront Resort with own Boat Slip
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths
  • rates (USD) $1,500 - $2,100 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

26 reviews write a review

Enjoy Sunrise By The Seashore! Luxuriously Appointed Sanctuary In Angler's Reef
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 5
  • baths
  • rates (USD) $1,800 - $2,250 /wk
 
 
 
 
 

12 reviews write a review

Luxury Waterfront Tropical Sunset Paradise
Windley Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 5
  • rates (USD) $1,000 - $1,250 /nt
    $28,000 /mth
 
 
 
 
 

3 reviews write a review

Upscale Family Friendly Gated Community - Oceanside Paradise
Windley Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,995 /wk
    $6,000 /mth
 
 
 
 
 

12 reviews write a review

Strikingly Beautiful Sunsets
Windley Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

6 reviews write a review

Super Penthouse - Futura Yahct Club #603
Windley Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $995 - $1,395 /wk
 
 
 
 
 

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Oceanfront at Anglers Reef, Steps From Pool and Ocean, Ocean View From All Sides
Windley Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths
  • rates (USD) $2,700 /wk
    $7,500 /mth
 
 
 
 
 

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Luxury Retreat Set In Paradise - 131 At Anglers Reef In Islamorada
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths
  • rates (USD) $1,825 - $2,400 /wk
    $6,000 - $6,500 /mth
 
 
 
 
 

12 reviews write a review

Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS
Windley Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

25 reviews write a review

Boat, Fish, Swim from Your Own Dock! Vr-003
Windley Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

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Anglers Reef, Boat Slips, Heated Pool, Oceanfront, Tommy Bahama Furniture
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $1,995 /wk
    $5,995 /mth
 
 
 
 
 

4 reviews write a review

SPECIAL 7DAY RATE $1450.(9/2/14-10/25/14)
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,575 - $2,100 /wk
 
 
 
 
 

12 reviews write a review

Venetian Waterfront Retreat Guaranteed Best Deal
Windley Key House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $6,500 /mth
 
 
 
 
 

2 reviews write a review

Spacious Islamorada Condo/town Home
Windley Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,250 - $3,750 /mth
 
 
 
 
 

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Rite On Ocean Sleeps 4
Windley Key Bungalow Rental Picture
  • bedrooms 1
  • rental type Bungalow
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

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Your Florida Keys Getaway.....
Windley Key Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 8
  • baths 4
  • rates (USD)
 
 
 
 
 

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The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip
Windley Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $2,450 /wk
    $7,000 /mth
 
 
 
 
 

2 reviews write a review