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295 Houses
NEW LISTING! Comfy retreat w/ separate cottage, patio, & pier
Pigeon Key house
1 bedroom / 1 bathroom / sleeps 2
Responds fast! avg. 3 minutes
Price per night from
$157
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. 3 minutes
Price per night from
$137
Canal front home w/ Gulf views, WiFi, balcony, access to open water - dogs ok!
Pigeon Key house
3 bedrooms / 3 bathrooms / sleeps 7
Responds fast! avg. 1 hour 51 minutes
Price per night from
$157
Sunny home w/ firepit, private pool, private gas grill, & tiki bar!
Pigeon Key house
2 bedrooms / 2 bathrooms / sleeps 4
Responds fast! avg. 3 minutes
Price per night from
$119
NEW LISTING! Dog-friendly oasis with pier, multiple living spaces & water views!
Pigeon Key house
5 bedrooms / 4 bathrooms / sleeps 12
Responds fast! avg. 3 minutes
Price per night from
$306
Dog-friendly house w/dock & cleaning station - near canals & parks
Pigeon Key house
3 bedrooms / 3 bathrooms / sleeps 6
Responds fast! avg. 3 minutes
Price per night from
$141
Charming & inviting beachside getaway w/ free Wi Fi-near dive shops & marina
Pigeon Key house
1 bedroom / 1 bathroom / sleeps 2
Responds fast! avg. 3 minutes
Price per night from
$76
Price per night from
$202
Two-story waterfront house w/water views, dock, central AC, free WiFi - Dogs ok!
Pigeon Key house
4 bedrooms / 4 bathrooms / sleeps 9
Responds fast! avg. 3 minutes
Price per night from
$228
Great rentals within 20 miles that match your search
“Amazing Sunset Water Views” from this Bayfront Summer Sea Condo in Islamorada
Islamorada condo
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$128
Price per night from
$179
“Relaxing atmosphere.” The house is great. Very clean, comfortable and cozy. As fishermen, we especially loved the location due to the easy access to Gulf. The only problem we had was the weather!! Definitely recommend this home!!
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$214
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$358
Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach
Islamorada house
2 bedrooms / 3 bathrooms / sleeps 6
Price per night from
$586
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$257
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$166
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$963
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$275
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$90
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$142
Come relax in Islamorada, the tropical jewel of the Florida Keys!!
Islamorada apartment
1 bedroom / 1 bathroom / sleeps 4
Responds fast! avg. 1 hour 49 minutes
Price per night from
$225
$2500 A MONTH FOR OCTOBER AND NOVEMBER. OCEANFRONT 2 BEDROOM/2 BATH CONDO
Islamorada condo
2 bedrooms / 2 bathrooms / sleeps 5
“Amazing view! Absolutely gorgeous!” My two teenage daughters and I stayed at this condo and it worked out perfect for us! The view is stunning, and I loved to just sit in the living room and look out at the ocean. The condo was very clean, and really nicely decorated. There were some beach chairs on the balcony that we used at the beach which was nice to have since we had flown to Florida. There were also beach towels to use. The kitchen was cute with everything you would need to cook, although we mainly just ate breakfast there. It is located away from traffic so nice and quiet. I swam in the pool once and it was warm like a bathtub. Felt good after a day at the beach. This was our first trip to the Keys, and I liked that we were centrally located. We were a couple hours from Fort Lauderdale where we flew in from, and a couple hours from Key West where we went for a day trip. We loved John Pennekamp State Park which is only about 20 minutes away, and swam with a manatee at Canon Beach. We also snorkeled with Robbie's in Islamorada which is 20 min. the other way from us. I would definitely stay there again if I return to the keys.
Responds fast! avg. 1 hour 47 minutes
Travelers’ Choice award
Price per night from
$139
Price per night from
$129
DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140
Islamorada apartment
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$170
“Wonderful way to start a new year” We truly enjoyed our stay in Key Largo. The house had everything we needed. We enjoyed fishing in the canal and there were even manatees two different days in the canal. The location of this property is excellent and allows for many great choices of restaurants. Alex was very responsive and helped us answer a lot of questions before and during our visit. We would love to return again.
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$154
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$641
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$899
Meagan's Beach House - Bayfront Home with Spectacular Sunrise and Sunsets
Key Largo house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$321
“Great place for a family” Wonderful place to stay! My family of 5 enjoyed the clean rooms and full kitchen. Easy access to private beach, restaurants, grocery store. Very safe neighborhood. The house was fully provided for our stay, Great access to John Pennycamp and the Everglades. We would definitely stay here again. Daniel A. was very easy to work with. We enjoyed coming home after a busy day of snorkeling to make supper and lounge on our own deck or wander down to the private beach to enjoy the evening. Having this home made our vacation very relaxing and enjoyable.
Price per night from
$77
Seas the Day in this Waterfront Home on Oceanside MM90
Tavernier house
5 bedrooms / 3 bathrooms / sleeps 14
Price per night from
$225
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$162
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$163
Islamorada - PARADISE FOUND 3 bedroom/2 bath
Islamorada townhouse
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$163
Responds fast! avg. 2 hours 31 minutes
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$184
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$222
“Awesome! Will stay there again and again.” What a great place in Key Largo. Plenty of room and a great location. Right across from Publix and near all of the fun. We rented a boat from Pennicamp which was a short ride away. This place is perfect for a family. Each kid had their own bedroom and my daughter loved the trundle! There is a boat ramp and beach area that is perfect for relaxing or having a picnic. The owner was so nice and always responded to my questions. Can't wait to go back. We will be adding this to our annual vacation. Way better than a hotel!
Price per night from
$146