Long Key Rentals

Updating...

age 0-16
110 Results

Relevance

Price: low to high

Price: high to low

Reviews

110 Houses

Welcome to Paradise

Long Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Dishwasher

All filters match

Price per night from

$206

Luxury beachfront home with pool in Islamorada

Layton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

Match: Dishwasher

All filters match

Price per night from

$589

Responds fast! avg. 2 hours 34 minutes

Match: Dishwasher

All filters match

Price per night from

$172

Great rentals within 20 miles that match your search

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Dishwasher

All filters match

Price per night from

$459

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$287

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$574

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$517

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$458

Windley Key, FL Keys

Islamorada caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Dishwasher

All filters match

Price per night from

$115

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Dishwasher

All filters match

Price per night from

$159

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Dishwasher

All filters match

Price per night from

$655

2 BEDROOM 2 1/2 BATH VILLA WITH PRIVATE PATIO AND PLUNGE POOL

Duck Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 13 minutes

Match: Dishwasher

All filters match

Price per night from

$339

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!

Match: Dishwasher

All filters match

Price per night from

$353

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$230

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. 2 hours 56 minutes

Match: Dishwasher

All filters match

Price per night from

$327

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. 2 hours 52 minutes

Match: Dishwasher

All filters match

Price per night from

$984

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.

Match: Dishwasher

All filters match

Price per night from

$401

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! :-)

Match: Dishwasher

All filters match

Price per night from

$215

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Dishwasher

All filters match

Price per night from

$501

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

Match: Dishwasher

All filters match

Price per night from

$2,295

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$356

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

Match: Dishwasher

All filters match

Price per night from

$1,148

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

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Dishwasher

All filters match

Price per night from

$1,492

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$264

Match: Dishwasher

All filters match

Price per night from

$333

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

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$1,148

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$287

Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Dishwasher

All filters match

Price per night from

$660

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Dishwasher

All filters match

Price per night from

$984

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Dishwasher

All filters match

Price per night from

$1,032

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Dishwasher

All filters match

Price per night from

$327

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

Match: Dishwasher

All filters match

Price per night from

$409

Match: Dishwasher

All filters match

Price per night from

$1,090

Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Dishwasher

All filters match

Price per night from

$1,475

BAYSIDE Villa

Islamorada villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Dishwasher

All filters match

Price per night from

$316

2-Story condo w/ panoramic views and balconies

Marathon condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Dishwasher

All filters match

Price per night from

$373

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Dishwasher

All filters match

Price per night from

$574

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Dishwasher

All filters match

Price per night from

$745

Viewing 38 of 110
rentals in Long Key

×

Also consider