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Price: high to low
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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
Responds fast! avg. 1 hour 51 minutes
Price per night from
$201
Great rentals within 20 miles that match your search
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
“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
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
Price per night from
$257
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
Responds fast! avg. 3 hours 28 minutes
Price per night from
$200
Price per night from
$1,221
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
Price per night from
$228
“Amazing Sunset Water Views” from this Bayfront Summer Sea Condo in Islamorada
Islamorada condo
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$114
“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
Price per night from
$285
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
“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
“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