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Long Key Rentals

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378 Houses

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$328

MY PARADISE

Layton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$275

Bay Harbour A-304- 7 night minimum

Long Key house

3 bedrooms / 3 bathrooms / sleeps 6

“Perfect” Stayed here for over a week to go fishing with the family. I would say its the perfect place to stay if you want to fish the keys. We rented a boat at Bud and Mary's and it was delivered right to the units slip. Bait and fuel is available right across the property from Mr. Lobster. Manatees and tarpon were always right in front of the boat slip too. 304 was also very clean. Its the perfect place to stay in the Keys. We will be back again next year!

Price per night from

$328

Penthouse Paradise | Developer Unit w/ Every ★ Upgrade Possible!!

Layton apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 53 minutes

Price per night from

$2,317

135 Gulfview Drive

Long Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$115

PELICAN LANDING

Layton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$263

2 BDR Penthouse w/ Breathtaking Views ~ Designer Furnished ~

Layton apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 53 minutes

Price per night from

$867

Safety Harbour Canalfront

Layton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$521

Presidential Retreat!!!

Layton house

7 bedrooms / 8 bathrooms / sleeps 16

Responds fast! avg. 51 minutes

Price per night from

$6,742

A Pirates Great Escape ~ 3bed/2baths Ocean View Slip ~LKKB

Layton condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 21 minutes

Price per night from

$618

Welcome to Paradise

Long Key townhouse

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$234

132 Atlantic Lane

Layton house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$172

Superior 4bd Penthouse with gym, movie room, and private rooftop lounge

Layton apartment

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 53 minutes

Price per night from

$4,645

Modern Oceanview Paradise at Islamorada

Layton house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 53 minutes

Price per night from

$4,584

The "Designated Paradise" - let this Bayside Estate take your breath away

Layton house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 53 minutes

Price per night from

$4,136

Luxury beachfront home with pool in Islamorada

Layton house

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 47 minutes

Price per night from

$1,149

Great rentals within 20 miles that match your search

Windley Key, FL Keys

Islamorada caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$131

DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$173

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

“Just what the family needed” The accommodations were just what we needed. Chris was a gracious host; she was available for anything we needed. The location and amenities fit our needs perfectly. We were able to swim and kayak in the channel, hang out in the tiki hut, play cards and share meals in the large kitchen. We were close enough to family members, restaurants, and attractions. The trip to Key West wasn't too bad either. Overall, a perfect rental!

Price per night from

$588

Florida Keys Fishing & Diving, waterfront Home heated pool, deep dock, parking

Marathon house

4 bedrooms / 5 bathrooms / sleeps 10

“PERFECT multi-family” House was great for us, our kids, and another family. It's a split-living type house, and was PERFECT!!! The pool was very nice, not too small. We spend most of the time on the boat, or in the pool. DEFINITELY recommend this house!!!!

Price per night from

$458

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$425

MARATHON MAJIC

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$327

Get out of the cold Feb.5-12, 2018 in Florida Keys at Marathon,The Hammocks

Marathon Shores villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$562

RENOVATED 2 BED MARATHON TOWNHOME w/ DOCK SPACE - WALK TO BEACH!

Marathon Shores townhouse

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$345

Palm Cottage - Upscale, 2BR/2BA, Cabana Club Pool

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$236

Florida Keys Beach Home Pool Fishing Diving

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG

Price per night from

$239

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

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$275

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all the essentials and then even the ones you forgot! It was wonderful to see a manatee swim up past the dock our first morning there. A very magical spot with generous hosts. It had everything we wanted and then some. After a week there and driving around the whole Keys it was 100% the most perfect choice for us. I miss those hammocks!

Price per night from

$261

Executive Bay Club- great unit, great location!,

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$155

Mile Marker 87 - Mina Bay - Oceanfront "Million Dollar View"

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$151

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$797

Key Colony Beach FL - Cay Condo

Key Colony Beach condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$229

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$229

Forever Sunset 5bed/3bath open water views with pool & dockage

Marathon house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$620

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$675

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$346

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,158

Florida Keys Vacation Villas Waterfront Family Friendly Pool Spa Deep Water Dock

Marathon villa

6 bedrooms / 5 bathrooms / sleeps 14

Responds fast! avg. 41 minutes

Price per night from

$1,000

Viewing 38 of 378
rentals in Long Key

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Top Destination reviews

MY PARADISE
My Paradise from architect's perspective

My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the main interior room (dining, den and kitchen) with the oversize teak deck. The deck itself is a marvel. A covered sitting area gets you out of the sun, with six teak sun loungers for warming up and working on your tan. The house is in a turtle nesting area, but is equipped with special yellow lights that give the beach a soft glow at night. The deck itself is fitted with a string of mini lights that give it a romantic glow at night. The entire interior is walled with pickled wood planking with clerestory windows that are complemented by recessed indirect lighting if you experiment with the myriad assortment of light controls. While the just-renovated kitchen can handle a group making meals, the second and third bedrooms, along with the second bath, make a nice mini-suite (the bedroom with the big bed has a private door to the bath, the real gem of the house is the master bedroom. The master suite has a bedroom with three walls of huge windows looking out onto the ocean. If you open the windows, you can fall asleep with the lapping of the waves as your lullaby. The entire house is fitted with motorized hurricane shutters for protection during storms. The master bath is huge and has an amazing walk-in shower that is roomy for two. The master closet, off the bathroom, is cedar lined and easily holds more than enough clothes for a month. The master suite has its own Hvac system, so you can cool it down on a balmy night for snuggling under the covers. The home has four TVs, a stereo system with speakers on the deck, Wi-Fi, cable and phone. There are swim fins, snorkels and masks for exploring the beach waters. My son and I came across a pair of manta rays that swam off as we watched in wonder. The beach is excellent for fishing, the boat dock is handy. Bring kayaks for funsee more
Bay Harbour A-304- 7 night minimum
outstanding, the placewas exactly how described by freewheeler.

This place was very nice and clean and exactly how it was described by Freewheeler. If we go to the keys in the future, we will definitely rent from them again. You don't mind paying as long as there are no surprises or dissapointments. … see more

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