20 Best Vacation Rentals in Long Key - Holiday Lettings - Cabins

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24 Vacation rentals

27

Vacation home in Long Key

Florida Keys / Long Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Slip into the beach lifestyle and leave the daily grind behind when you book your stay at this oceanfront Layton cottage. With a dock, expansive deck, and a stunning beach location, you may never want to leave. With historic roots as the home to the 1900's author, Zane …see more

from $185 / night

$1295 / week

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from $185 / night

24

Vacation home in Long Key

Florida Keys / Long Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
Minimum Rental: 28 Days "Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable …see more

from $250 / night

$1750 / week

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from $250 / night

18

Vacation caravan/mobile home in Long Key

Florida Keys / Long Key

1 5 30 nights min

  • 1 bedroom
  • Sleeps 5
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Gated community spacious double wide mobile home, 1 bedroom - with 32' Flat Screen TV, Queen size bed, 2 full baths, Living room with 55 ' Flat Screen . 2 sleeper sofas 1-Double, 1-Queen), well equipped Kitchen, clothes washer & dryer, sleeps 5. 24 hour security, beaut …see more

from $64 / night

$448 / week

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avg. 2 hours 4 minutes

from $64 / night

(1) Excellent 

42

Vacation home in Long Key

Florida Keys / Long Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Discover the very best of the Florida Keys in this charming pet-friendly rental with a dock and beach! The unique home offers the makings of a romantic getaway or intimate retreat with friends. The rental is three miles from town and a few hundred feet from the Long Key …see more

from $180 / night

$1260 / week

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from $180 / night

(12) Very Good 

23

Home rental in Long Key

Florida Keys / Long Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Beautiful 3 bedroom and 2.5 luxury condo located at mile marker 74.5 bayside.  This condo is nicely decorated and very spacious for you and your family. The unit has a great screened in porch off the living room.  The complex has 2 tennis courts, weight room, dockage, p …see more

from $228 / night

$1600 - $2500 / week

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from $228 / night

24

Long Key Vacation townhouse rental

Florida Keys / Long Key

2 5 30 nights min

  • 2 bedrooms
  • Sleeps 5
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Ocean view 2 bedrooms 3 baths right across from heated community pool, convenience store and club house. Location Location Location. 50' TV, golf cart available, all high end appliances, furniture, houseware and kitchenware . All you need to bring is your clothes, bath …see more

from $179 / night

$1250 / week

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from $179 / night

49

Vacation home in Long Key

Florida Keys / Long Key

6 14 28 nights min

  • 6 bedrooms
  • Sleeps 14
  • 28 nights min
  • Child friendly
  • Air conditioning
Fill your days with luxury and relaxation when you book your stay at this top-notch Long Key home. With a swim-up bar, a private pool, a hot tub, and a private beach, you won't have to go far for fun. Two-and-a-half miles from Layton, and 14 miles to Marathon, this quie …see more

from $580 / night

$4060 / week

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from $580 / night

17

Apartment rental in Long Key

Florida Keys / Long Key

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
From the minute you step foot in this luxurious condo, the water dominates your view and your activities. Oceanfront views from living room and master bedroom, 3 balconies... lush gardens, pool, palm trees, the finest sandy beach in the keys and the magnificent Atlantic …see more

from $167 / night

$1167 / week

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from $167 / night

(1) Excellent 

25

Vacation home in Long Key

Florida Keys / Long Key

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
Minimum Rental: 28 Days "Sea Grape" is a serene, quaint part of paradise that the entire family will enjoy at this ultra-charming BEACH HOUSE just footsteps from the SEA. Come and stay in this adorable home located on the crystal clear Atlantic Ocean! The home has p …see more

from $194 / night

$1358 / week

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from $194 / night

11

Vacation apartment in Long Key

Florida Keys / Long Key

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Large 2 bedroom condo in a beautiful setting. Pool, tennis court, boat/fishing dock, tiki bar, BBQs. Quiet complex with only 30 condos total, just past Long Key State Park and next to 2.5 mile bridge. Kayaking, boating, biking or just relaxing. …see more

from $3000 / night

$21000 / week

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from $3000 / night

49

Long Key Vacation home rental

Florida Keys / Long Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Pack your bags!  We've got the perfect vacation home for you and your family!  This adorable 3 bedroom/2 bath home is located on a deep water canal at the 74 mile marker Bayside.  Great yard with room for your boat trailer!  All 3 bedrooms are on one floor.  House is st …see more

from $133 / night

$931 / week

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from $133 / night

24

Home rental in Long Key

Florida Keys / Long Key

3 8 28 nights min

  • 3 bedrooms
  • Sleeps 8
  • 28 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Let this picturesque 3-bedroom, 2-bathroom Islamorada vacation rental house serve as the perfect setting for your next trip to Florida! Featuring comfortable sleeping space for 8, top-notch amenities and an unrivaled location near beaches and main attractions - this all …see more

from $133 / night

$933 - $1400 / week

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from $133 / night

24

Vacation home in Long Key

Florida Keys / Long Key

1 2 28 nights min

  • 1 bedroom
  • Sleeps 2
  • 28 nights min
  • Child friendly
  • Air conditioning
This Long Key suite provides the perfect place for your next vacation to the Florida Keys, from the white sand beach right out the back door to a large pool with a swim-up bar! Famous from the Netflix series "Bloodline," Layton is a great combination of small-town tranq …see more

from $122 / night

$854 / week

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from $122 / night

29

Vacation home in Long Key

Florida Keys / Long Key

3 8 28 nights min

  • 3 bedrooms
  • Sleeps 8
  • 28 nights min
  • Child friendly
  • Air conditioning
Luxury will be at your fingertips when you book your next family getaway to this Long Key retreat with amenities like a pool, hot tub, kayaks, a swim-up bar, and access to a beach. Set right on the beach, you'll be just two miles from Long Key State Park and two-and-a-h …see more

from $253 / night

$1771 / week

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from $253 / night

24

Vacation villa with swimming pool in Long Key

Florida Keys / Long Key

2 5 30 nights min

  • 2 bedrooms
  • Sleeps 5
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Ocean view 2 bedrooms 3 baths right across from heated community pool, convenience store and club house. Location Location Location. 50' TV, golf cart available, all high end appliances, furniture, houseware and kitchenware. All you need to bring is your clothes, bathi …see more

from $147 / night

$1029 / week

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from $147 / night

45

Vacation home in Long Key

Florida Keys / Long Key

2 4 28 nights min

  • 2 bedrooms
  • Sleeps 4
  • 28 nights min
  • Child friendly
  • Air conditioning
Everyone wants to leave their worries behind and escape on a soothing beachfront vacation - why not make your next one something special? This top-floor Long Key condo has it all: a gorgeous white sand beach, a shared swimming pool with a swim-up bar, and an amazing sel …see more

from $205 / night

$1435 / week

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from $205 / night

28

Long Key Vacation home rental

Florida Keys / Long Key

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Pelican House, is a 3 bedroom, 2.5 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (h …see more

from $560 / night

$3920 - $5390 / week

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from $560 / night

27

Vacation home in Long Key

Florida Keys / Long Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Stroll along the postcard-perfect beaches as you let the warm tropical breezes swirl around you at this beachfront Islamorada home. The prime seaside setting is the ideal spot to let the stress melt away as you revel in ocean adventures and long walks on the sandy shore …see more

from $111 / night

$777 / week

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from $111 / night

26

Vacation home rental

Florida Keys / Long Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi.  The Bay Harbour Complex comes complete with two tennis courts, weight room, pool, your own dedi …see more

from $228 / night

$1600 - $2500 / week

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from $228 / night

15

Vacation home in Long Key

Florida Keys / Long Key

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Child friendly
Located at MM 73 in Lower Matecumbe, Islamorada - this 3 bedroom and 2.5 bath will sure to be your home away from home.  Nicely decorated and very comfortable.  You can sit outside in the hot tub and enjoy the peaceful canal.  Great home for your next vacation. Near the …see more

from $166 / night

$1162 / week

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from $166 / night

27

Vacation home in Long Key

Florida Keys / Long Key

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Pet friendly
Enjoy a getaway in one of Islamorada's most prestigious neighborhoods when you rent this three-bedroom, three-bathroom home. Located at the end of a cul-de-sac within the Port Antigua neighborhood on Lower Matecumbe Key, the home quickly enchants arriving guests with it …see more

from $150 / night

$1050 / week

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from $150 / night

29

Vacation home with shared pool in Long Key

Florida Keys / Long Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Cozy, canalfront, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The bedrooms are located in a separated, quiet part of the house, while the living, dining, and kitche …see more

from $166 / night

$1162 / week

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from $166 / night

10

Vacation home in Long Key

Florida Keys / Long Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi- …see more

from $100 / night

$700 / week

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from $100 / night

26

Vacation home in Long Key

Florida Keys / Long Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Awesome renovated home in Port Antigua.  The upstairs has 3 bedrooms and 2 baths.  The kitchen has granite counter tops, stainless steel appliances, along with a serving window if you are out on the balcony.  The downstairs has a great tv room with a sectional and a kit …see more

from $180 / night

$1260 / week

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from $180 / night