10 Best Vacation Rentals in Lower Keys - Holiday Lettings - Cabins

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Vacation rentals Summerland Key
9 properties

Lower Keys

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329 Vacation rentals

33

Vacation home in Lower Keys

Florida Keys / Lower Keys

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 13 mi
  • Child friendly
  • Air conditioning
Welcome to Duck Key Vacation Rentals! Located on a private island in the Florida Keys, our Duplex is the perfect spot for your next vacation! Within walking distance, you’re only minutes away from many outdoor activities like fishing, diving, snorkeling, dolphin encoun …see more

from $200 / night

$1,400 - $2,135 / week

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from $200 / night

24

Vacation home in Little Torch Key

Lower Keys / Little Torch Key

3 7 30 nights min

  • 3 bedrooms
  • Sleeps 7
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This 3 BR, 2 BA home offers so many special features all in one perfect location! Situated around the corner from Dolphin Marina, a quick 60 second trip down the canal puts you directly to open water offering access to both the Gulf and Ocean. The canal has a depth of 8 …see more

from $150 / night

$1,050 / week

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Responds fast!
avg. 31 minutes

from $150 / night

(1) Excellent 

20

Vacation home with swimming pool in Summerland Key

Lower Keys / Summerland Key

3 10 30 nights min

  • 3 bedrooms
  • Sleeps 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Amazing canal front 3 bed 2 bath open concept house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see l …see more

from $159 / night

$1,113 / week

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from $159 / night

(1) Excellent 

50

Summerland Key Vacation home rental

Lower Keys / Summerland Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxurious, but cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands, the most prominent of which is Looe Key reef, a popular diving/snorkeling area. (There is an island, located a few miles out directly in front …see more

from $392 / night

$2,744 / week

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Responds fast!
avg. 3 hours 43 minutes

from $392 / night

19

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
PARADISE LIVING: Enjoy the view from our large porch overlooking a deep, wide, crystal blue clear canal with quick boating access to the Atlantic Ocean. Looe Key Coral Reef is a short distance away by boat for some of the best diving and fishing the keys has to offer. I …see more

from $99 / night

$693 / week

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from $99 / night

29

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Stay in this three-bedroom, two-bath canal front villa for six when you come to Summerland Key and revel in rest and relaxation with your very own private pool and hot tub. And to make your vacation complete, you can bring three dogs along for a small nightly fee! This …see more

from $152 / night

$1,064 / week

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Responds fast!
avg. 24 minutes

from $152 / night

17

Summerland Key Vacation home rental

Lower Keys / Summerland Key

2 8 28 nights min

  • 2 bedrooms
  • Sleeps 8
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a 28 Day MINIMUM Rental, Please do not contact us for less. Thank You. Large Heated POOL with separate bath, 15K Boat lift, Totally remodeled (2017) waterfront home. Will accommodate 6 people very comfortably, with both a fold out and lower overflow room. This …see more

from $150 / night

$1,050 - $1,260 / week

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from $150 / night

13

Home rental in Summerland Key with swimming pool

Lower Keys / Summerland Key

5 8 30 nights min

  • 5 bedrooms
  • Sleeps 8
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
3 Bedroom / 2 Bath Upstairs 1 King Bed, 2 Queen Spacious office with open water views 2 Bedroom/ 1 Bath Down 1 King, 2 twin 2 Separate living room areas, up and down, each with large flat screen TV's and DVD players Large screened porch up and down Heated Pool w/ …see more

from $184 / night

$1,284 / week

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from $184 / night

27

Home rental in Summerland Key

Lower Keys / Summerland Key

5 10 30 nights min

  • 5 bedrooms
  • Sleeps 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
"Casa Manana," the name affectionately assigned this beautiful gated property in Summerland (Ramrod) Key, is a uniquely situated private waterfront venue. Enter through the gates and you will immediately be transported into the tranquil, easygoing and thoroughly relaxi …see more

from $667 / night

$4,667 / week

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from $667 / night

14

Home rental in Summerland Key

Lower Keys / Summerland Key

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning
Stunning Atlantic Ocean views from dining area, living room and both bedrooms. Sunrise on the left, sunset on the right and in between 180 degrees of open ocean. Our vacation home is located in exclusive Summerland Key (mile marker 24.5). Whether you are daring adventu …see more

from $140 / night

$980 / week

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from $140 / night

4

Vacation cottage in Summerland Key

Lower Keys / Summerland Key

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Child friendly
Hidden Hammock Resort is located in Summerland Key, the Florida Keys' best kept secret! Our premium location just 23 miles from Key West allows you to enjoy the festivities and nightlife of Duval Street while still having a nice and quiet retreat to come back to. When y …see more

from $140 / night

$980 / week

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from $140 / night