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Long Key Rentals

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204 Houses

MY PARADISE

Layton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$275

PELICAN LANDING

Layton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$400

2 BDR Penthouse w/ Breathtaking Views ~ Designer Furnished ~

Layton apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 56 minutes

Price per night from

$1,432

Welcome to Paradise

Long Key townhouse

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$205

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

Layton apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 56 minutes

Price per night from

$2,279

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

Layton apartment

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 56 minutes

Price per night from

$4,569

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

Layton house

6 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 56 minutes

Price per night from

$4,867

Modern Oceanview Paradise at Islamorada

Layton house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 56 minutes

Price per night from

$4,569

Luxury beachfront home with pool in Islamorada

Layton house

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 28 minutes

Price per night from

$596

Supreme 7bd Ocean View Penthouse with 2 rooftop lounges, gym, sauna, movie room

Layton apartment

7 bedrooms / 6 bathrooms / sleeps 16

Responds fast! avg. 56 minutes

Price per night from

$5,725

Great rentals within 20 miles that match your search

Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise

Conch Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 34 minutes

Price per night from

$189

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

Studio / 1 bathroom / sleeps 2

“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.

Price per night from

$172

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

$258

Escape to Paradise --2 bedroom oceanfront condo on Coco Plum

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Beautiful location with lots to enjoy!!” This property is exactly as pictured! It was a wonderful vacation with an ideal location.It was right on the ocean so you could watch the sun rise through the screened lanai, along with other various ocean activities.The owners were wonderful to work with and even apologized about parking lot maintenance being completed during our visit, which was no big deal. Please be aware that the property has one of the rare sand beaches in the Keys but seaweed washes up also. Although it can be unsightly, it didn't bother me. The beachcomber does come every few days to clean it up. There was still plenty of sand to the left (North) for me to walk on the beach and search for baby shells. There are so many places to choose for dinners. I recommend Havanna Jack's for oceanfront dining, Florida Keys Steak and Lobster House for lobster, Burdine's for fries and sunset, and Key Colony Inn for early bird special.I truly enjoyed the Dolphin Research Center and also seeing a turtle release from the Turtle Hospital at Sombrero Beach. I enjoyed the heated pool every day because the weather was perfect! If you aren't familiar with the Keys, Marathon is the middle Key. We went to Key West for the day (1 1/2 hr drive) because my friend had never experienced it. The ladies at the Marathon Visitor Center were the best! Great souvenir shop was Marooned in Marathon. You will not believe how many unique gifts they have. I plan to return to this Coco Plum property if/when I am lucky enough to go back to the Keys! I feel we saw alot but there is still so much more to enjoy!

Price per night from

$287

Amazing Ocean View Condo on the Beach!

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

Responds fast! avg. 3 hours 11 minutes

Price per night from

$343

Now booking Spring/Summer 2021! Dock, Bikes, Kayak, 2 beach clubs

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful Place to Stay” Place was exactly as described! Has all of the amenities needed for a relaxing, sun filled vacation! Pool, beach, location is perfect for any stay in the Florida Keys. Central to everything!

Responds fast! avg. 1 hour 28 minutes

Price per night from

$287

Kokomo Cove Boat House

Marathon house

2 bedrooms / 2 bathrooms / sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

Price per night from

$257

Royal Palm House

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful Home in Marathon” We truly loved this place, the home was clean, spacious and very comfortable! My husband still claims to this day that was the best sleep he has had in years and that's a big compliment coming from him! We loved having water access (although we didn't have a boat) it really made for some beautiful sunsets and sunrises! We found a couple of amazing restaurants that we visited on several occasions, the first and our favorite was Tarpon Creek following as a very close second was The Sunset Grill and Raw Bar, also our favorite breakfast spot became Juice Paradise Cuban Cafe (the best coffee). I'm only just now getting around to reviewing this place because we are planning another trip to the Keys in December and I was checking this place out and i didn't see our review and ask my husband about it (I thought he posted it and he thought I posted it), so finally 2 yrs later I'm giving our review!!! Unfortunately I see it's booked for our time frame and we are very disappointed about that but I know whoever booked it WILL NOT be disappointed! Thanks so much for an amazing experience, Gina & Scott PS we actually stayed Sept 2014 but it would only let me go back to Oct 2014! :-)

Price per night from

$214

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 43 minutes

Price per night from

$1,718

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$344

Private Island Rental with 19' Boat, Seabird Key

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“Heaven On Earth!” From the moment you step foot on this beautiful island paradise, you'll feel like you've been transported to your own little private world! Every amenity has been thought of from an outstanding outdoor kitchen, complete with state of the art grill, oven and microwave along with dinnerware, glassware etc. Not to mention the kitchen inside the house comes complete with all you need also. Even spices, just not food! The house itself is amazing and has a awesome stereo system so you can have music in the house, on the decks and on then beach! You can snorkel, swim, fish, sail, canoe, kayak, go tubing walk along the perfectely maintained tropical paths. From sunrise to sunset you day will be filled with beautiful scenerey, The view from the front porch is my favorite, I could sit there all day and have! This was our 7th trip and we had a extended stay of 10 glorious days, also our first trip with friends who loved it as much as we do! We've spent my birthday and our anniversary (back to back) here many of times and there is no place else we would rather be! The island is alive with hermit and land craps and Iguanna's and birds of all sorts. It's so funny to see a hermit crap go by with some sort of object he found as a shell. At night when you turn all the outside lights on it's like a magical transformantion! I can not say enough good things about Seabird Key. The owners and care takers do such a amazing job! Thank you for sharing this tropical paradise with us and we hope to be back again soon!

Price per night from

$1,472

OCEANFRONT LUXURY "Mar Azul"

Marathon house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 15 minutes

Price per night from

$500

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

$287

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$355

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

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$271

OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problems. I would highly recommend this rental

Responds fast! avg. 3 hours 11 minutes

Price per night from

$735

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

$516

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,718

Windley Key, FL Keys

Islamorada caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$115

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$158

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$654

FALL SPECIAL STAY 4 NIGHTS GET 5TH NIGHT FREE $225 NIGHTLY

Duck Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$338

Reef Resort - Peaceful Getaway 204

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

Price per night from

$271

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

Price per night from

$196

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 4 minutes

Price per night from

$206

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 33 minutes

Price per night from

$114

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

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$458

Viewing 38 of 204
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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