Pigeon Key Rentals

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355 Houses

NEW LISTING! Dog-friendly retreat w/ patio & wrap-around deck - near the water!

Pigeon Key caravan/mobile home

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 49 minutes

Price per night from

$73

NEW LISTING! Dog-friendly oasis with pier, multiple living spaces & water views!

Pigeon Key house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 34 minutes

Price per night from

$261

NEW LISTING! Cozy home w/ community boat ramp, walk to bay, near attractions

Pigeon Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 6 minutes

Price per night from

$114

NEW LISTING! Comfy retreat w/ separate cottage, patio, & pier

Pigeon Key house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$129

NEW LISTING! Charming & inviting beachside getaway-close to dive shops & marina

Pigeon Key house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 52 minutes

Price per night from

$36

NEW LISTING! Dog-friendly house w/dock & cleaning station - near canals & parks

Pigeon Key house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 12 minutes

Price per night from

$133

FISHERMANS PARADISE IN THE MIDDLE KEYS1

Pigeon Key house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 51 minutes

Price per night from

$201

Great rentals within 20 miles that match your search

Paradise at Islamorada

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$162

Newly updated cottage in the heart of Key Largo

Tavernier cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$104

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 55 minutes

Price per night from

$200

Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$521

Best Value at OceanPointe & FL Keys+Family Friendly Ocean Front & Mangrove Views

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful location & great facilities on the ocean.” Our unit had a cool view of mangroves & the ocean. Great pool & hot tub. Excellent restaurants near & only 2 hrs. to Key West. Only needed 1 day in Key West.

Price per night from

$200

Our Kozy Key - Paradise FUN at your door.

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Cozy and Convenient” The townhouse was located right outside the pool and private lagoon which was perfect for traveling with small children. The place was clean and fresh smelling and the decor is bright and inviting as a beach house. There were more than expected amenities which made our stay as comfortable as being at home.

Responds fast! avg. 2 hours 32 minutes

Price per night from

$143

Enjoy the Florida Keys!

Tavernier condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$183

Fabulous and Spacious HOME!!

Ocean Reef house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$145

Tropical 3-level, End-unit Condo With 3 Bedrooms, 3 Bathrooms Water View#

Key Largo townhouse

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$285

CASA MAR WATERFRONT VILLA! CHIC COASTAL STYLE! VOTED BEST RENTAL IN KEY LARGO!

Key Largo townhouse

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 16 minutes

Price per night from

$505

Oceanfront Condo at Ocean Pointe Resort

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

Gorgeous updated Bayview condo

Key Largo condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 10 minutes

Price per night from

$163

Good Times and Tan Lines - (New Listing) Deluxe Renovated Ocean View 2B/2B Condo

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$244

Ocean pointe island retreat

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 28 minutes

Price per night from

$200

Key Largo Waterfront Estate

Key Largo house

10 bedrooms / 8 bathrooms / sleeps 20

Price per night from

$1,221

Premier Condo in Upper Florida Keys

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$244

Gorgeous Ocean Side Home! Pool, Tiki Hut, 65' Dock, Ice Maker, Fishermans Dream

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 13

Price per night from

$248

Margarita Beach House at The Keys

Tavernier house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$228

Price per night from

$114

Key Largo Paradise Point ! CALL FOR SPECIALS!!!

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

“LOVE! LOVE! LOVE!” I really loved this place for my family! We saw a ton of manatees right from the dock. We loved having coffee and breakfast and watching them from the deck. The house was perfect...comfortable and clean with all the amenities. And even though we brought our kayaks, they had great ones there. Can't wait to go back!

Responds fast! avg. 3 hours 6 minutes

Price per night from

$371

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$285

Oceanfront Therapy. Relax and enjoy the Ocean

Tavernier house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$160

Great Catch for Fisherman and Boaters in Key Largo

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

Price per night from

$200

Beautiful Sunsets On A 2 Acre Estate With Water Views From Almost Every Room !!!

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$513

Sep 3-Dec 1 Open! EZ Ocean Access*Boat Slip*Roof Top Deck*Hot Tub*28 nt min

Key Largo house

3 bedrooms / 4 bathrooms / sleeps 6

“Great Key Largo Rental” We rent homes on the water in the Keys frequently. By far this is the best home we have rented. House is immaculate, fully equipped,and only a short ride to the ocean. On water gas super close. Restaurants within walking distance. Management company is awesome, very responsive and prompt.

Responds fast! avg. 2 hours 24 minutes

Price per night from

$182

LIVE THE LAVISH KEYS LIFE! CONTEMPORARY VIBRANT, AIRY AND BEACHY! FREE GOLF CART

Key Largo townhouse

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 16 minutes

Price per night from

$313

Private Hotel Rm 2 -Beach-Marina

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 2

“Great place to stay” If your looking for a place to just stay the night this place is perfect. Comfy, clean, and updated!

Responds fast! avg. 2 hours 5 minutes

Price per night from

$100

3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$269

Tropical Cottage with Sandy Beach

Key Largo cottage

2 bedrooms / 2 bathrooms / sleeps 6

“Key Largo” Our stay was great. The house was awesome and we would go swimming and fishing right off the dock. Its a great place for the family to have a vacation.

Price per night from

$229

San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 24 minutes

Price per night from

$818

Fabulous 2 level home - 3/2 each Level - Waterfront Pool Home in Islamorada!

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 44 minutes

Price per night from

$287

Viewing 38 of 355
rentals in Pigeon Key

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