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

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346 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 $300 / night

$2,100 / week

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avg. 1 hour 28 minutes

from $300 / night

(1) Excellent 

22

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 $75 / night

$525 / week

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Responds fast!
avg. 3 hours 11 minutes

from $75 / night

26

Vacation home rental

Florida Keys / Long Key

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 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

$2,000 - $2,750 / week

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from $228 / night

(1) Excellent 

5

Vacation home in Long Key

Florida Keys / Long Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
MINIMUM STAY: 28 DAYS FABULOUS BEACH HOUSE located directly on a mile long sandy beach. Minimum Rental is 1 month. The original "Sea Grape" was destroyed by Hurricane Irma in September 2017. The decision was made to tear down and rebuild. The new Sea Grape is cu …see more

from $193 / night

$1,351 / week

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from $193 / 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 $3,000 / night

$21,000 / week

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from $3,000 / night

(1) Excellent 

37

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
  • Pet friendly
Discover the very best of the Florida Keys in this charming dog-friendly (for an additional fee) 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 hundr …see more

from $300 / night

$2,100 / week

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Responds fast!
avg. 1 hour 28 minutes

from $300 / 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 qu …see more

from $580 / night

$4,060 / week

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Responds fast!
avg. 1 hour 28 minutes

from $580 / night

(12) Very Good 

29

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 bath luxury penthouse condo located at mile marker 74.5 bayside.  This condo is nicely decorated, fully appointed, and very spacious for you and your family. The unit has a beautiful screened-in lanai off the living room and master bedroom wi …see more

from $229 / night

$2,000 - $2,750 / week

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from $229 / 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 …see more

from $253 / night

$1,771 / week

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avg. 1 hour 28 minutes

from $253 / 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

$1,435 / week

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Responds fast!
avg. 1 hour 24 minutes

from $205 / night

22

Vacation home with shared pool in Long Key

Florida Keys / Long Key

3 4 28 nights min

  • 3 bedrooms
  • Sleeps 4
  • 28 nights min
  • 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 downstairs only of this house is rented.  Super cute 2 bedroom.  No one would be in the upstairs w …see more

from $133 / night

$931 / week

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from $133 / night

27

Vacation home in Long Key

Florida Keys / Long Key

3 7 28 nights min

  • 3 bedrooms
  • Sleeps 7
  • 28 nights min
  • 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

$1,050 / week

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from $150 / 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

$1,167 / week

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from $167 / night

38

Vacation home in Layton

Long Key / Layton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
A true beach bungalow with a slice of private shoreline and a dock to boot, this full duplex is perfect for a relaxing getaway. Gather the whole family, including your canine pals (for a small nightly fee), and head to the land of sunshine and shorelines. One dog is als …see more

from $600 / night

$4,200 / week

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avg. 1 hour 34 minutes

from $600 / night

13

Layton Vacation home rental

Long Key / Layton

2 6 28 nights min

  • 2 bedrooms
  • Sleeps 6
  • 28 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Looking for your next Home away from Home? You can not go wrong in this recently renovated 2 bedroom and 2 bath canal home in Lower Matecumbe at the 76 Mile Marker . This home has everything you need for your next get-away in Islamorada. Only one property away from t …see more

from $133 / night

$931 / 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 tran …see more

from $122 / night

$854 / week

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Responds fast!
avg. 1 hour 43 minutes

from $122 / 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

$1,250 / week

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from $179 / night

24

Home rental in Long Key

Florida Keys / Long Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

Pricing unknown

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Responds fast!
avg. 31 minutes

Pricing unknown

26

Vacation home in Long Key

Florida Keys / Long Key

3 8 28 nights min

  • 3 bedrooms
  • Sleeps 8
  • 28 nights min
  • 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

$1,260 / week

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from $180 / night

10

Vacation home in Long Key

Florida Keys / Long Key

2 4 28 nights min

  • 2 bedrooms
  • Sleeps 4
  • 28 nights min
  • 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

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

$3,920 - $5,390 / week

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from $560 / night