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Long Key Rentals

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204 Results

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204 Houses

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. 1 hour 38 minutes

Price per night from

$1,379

Welcome to Paradise

Long Key townhouse

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$198

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

Layton apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 38 minutes

Price per night from

$1,349

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

Layton apartment

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

Price per night from

$2,810

Modern Oceanview Paradise at Islamorada

Layton house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 38 minutes

Price per night from

$1,517

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

Layton house

6 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 1 hour 38 minutes

Price per night from

$3,259

Luxury beachfront home with pool in Islamorada

Layton house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 23 minutes

Price per night from

$842

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

Layton apartment

7 bedrooms / 6 bathrooms / sleeps 16

Responds fast! avg. 1 hour 38 minutes

Price per night from

$3,371

Responds fast! avg. 2 hours 38 minutes

Price per night from

$172

Great rentals within 20 miles that match your search

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

$552

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. 2 hours 45 minutes

Price per night from

$330

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

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 5

“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 48 minutes

Price per night from

$248

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Price per night from

$243

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$342

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

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$261

SANCTUARY IN PARADISE

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 3 hours 28 minutes

Price per night from

$945

CARIBBEAN SOUL SAILING CHARTER Bayfront 2 BR cottage w/ 23 foot Sailboat or dock

Conch Key cottage

2 bedrooms / 1 bathroom / sleeps 6

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

Responds fast! avg. 3 hours 58 minutes

Price per night from

$315

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

$206

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

$206

Bayside Condo, marina, pool and beach

Islamorada condo

3 bedrooms / 2 bathrooms / sleeps 6

“The Best Keys Location” My family stayed at this lovely Futura Yacht Club Condo for three weeks this July. We have stayed at many other units in this complex over the years but this unit was one of the nicest we have seen. The unit has been remodeled and it has everything you would need for a great Keys vacation. Futura Yacht club has a big heated pool, tennis courts and if you are a boater a great marina with its own boat ramp which made it easy for us to enjoy our boat and jet ski's. It is a gated complex with security, centrally located to all the activities & restaurants in the area. We found the owner most helpful, accommodating and easy to deal with. We are looking forward to our next stay!!

Responds fast! avg. 2 hours 24 minutes

Price per night from

$244

the private & secluded PENINSULARHOUSE off Grassy Key harbor in Marathon.

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

“Nice get away” Beautiful and relaxing. Did alot of snorkeling right off the deck. Enjoyed the paddle boats and the kayaks. When we make it down that way again I would definitely stay here.

Price per night from

$482

OCEANFRONT LUXURY "Mar Azul"

Marathon house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$481

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

$276

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

$497

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$331

Executive Bay Club- great unit, great location!,

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 28 minutes

Price per night from

$189

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$552

Keys Kottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$260

Islamorada cottage on deep water canal

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

Price per night from

$276

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$552

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$147

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

Price per night from

$3,970

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

$938

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,970

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$440

Windley Key, FL Keys

Islamorada caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$111

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

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$153

Viewing 38 of 204
rentals in Long Key

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Top Destination reviews

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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