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

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Vacation rentals Summerland Key
19 properties

Lower Keys

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21 Vacation rentals

12

Vacation home in Summerland Key

Lower Keys / Summerland Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This lovely 2 bedroom, 2 bath residence is located on Summerland Key at mile marker 24 just north of Key West for sightseeing, great restaurants or just take in the color of the local history in our southernmost most city. The home is comfortably furnished in tropical c …see more

from $84 / night

$584 / week

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from $84 / night

14

Vacation home in Summerland Key

Lower Keys / Summerland Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining ar …see more

from $110 / night

$770 / week

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from $110 / night

15

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Summerland Place is just what the doctor ordered. Fabulous weather, boating and diving every day plus a sweet place to call home. Located at mile marker 25 with some of the best boating access in the area. The main level has 2 bedrooms, a bathroom, kitchen and living ro …see more

from $117 / night

$817 / week

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from $117 / night

10

Lower Keys Vacation home rental

Florida Keys / Lower Keys

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all that great, fresh fish you're gonna catch. Easy ride under some bridges …see more

from $86 / night

$601 / week

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from $86 / night

35

Summerland Key Vacation home rental

Lower Keys / Summerland Key

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • 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 $300 / night

$2100 / week

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from $300 / night

24

Vacation home in Lower Keys

Florida Keys / Lower Keys

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Ask about pets
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 $433 / night

$2200 - $2410 / week

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from $433 / night

12

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42" Sony flat-screen, hi-def TV with surround sound makes you feel like you are right in the middle of the action. Kit …see more

from $200 / night

$1400 / week

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from $200 / night

13

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
The open porch catches the breeze and sun with this Florida Keys vacation rental! Sit back and relax in this clean, airy, and spacious vacation home. Located on a canal and equipped with all the comforts of home. This tropical setting will set your mind at ease in a tru …see more

from $100 / night

$700 / week

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from $100 / night

14

Home rental in Summerland Key

Lower Keys / Summerland Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $200 / night

$1400 / week

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from $200 / night

13

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Enjoy this large oceanfront home on Summerland Beach. This expansive 3 bedroom, 2 bathroom home is just perfect for large families and big boats. Over 2,500 square feet of living space with lots of room for everyone to spread out. The kitchen has plenty of room for ever …see more

from $234 / night

$1634 / week

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from $234 / night

18

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Enjoy many peaceful days and evenings at Cruikshank Isle, situated right on the tip of Cruikshank Island on Summerland Key where astounding sunsets and ocean vistas will be yours. The grounds are very shady and groomed with a nice Tiki hut at the waters edge. Plenty of …see more

from $168 / night

$1176 / week

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from $168 / 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 $119 / night

$833 / week

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from $119 / night

18

Vacation villa in Summerland Key

Lower Keys / Summerland Key

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Melody Key is probably the best kept secret in the magnificent Florida Keys. The Florida Keys are totally unique and the locals are probably the friendliest on the planet. The Keys are famous for their natural beauty and nature: One hundred and thirteen miles of …see more

from $1250 / night

$9625 / week

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from $1250 / night

12

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Just imagine...Balmy southeast winds are blowing with a perfect Florida Keys sunset right in front of you, while relaxing in your comfy lawn chair with a frozen margarita. This could be you if you choose Ocean Breeze for your next Florida Keys adventure. Located on Summ …see more

from $164 / night

$1144 / week

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from $164 / night

13

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys. This stylish home is outfitted in Florida tropical style with cool and …see more

from $207 / night

$1447 / week

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from $207 / night

22

Vacation home in Summerland Key

Lower Keys / Summerland Key

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. This beautiful home has three stories including a super play room off the pool area with a ping-pong table and a big screen TV for the kids. The 2n …see more

from $200 / night

$1400 / week

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from $200 / night

24

Vacation home rental

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef's dream with top of the line stainless appliances, cook top, built in ovens and gorgeo …see more

from $267 / night

$1867 / week

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from $267 / 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

$1284 / 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

$4667 / week

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from $667 / night

18

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Enjoy the ultimate peace and quiet offered on Big Torch Key. Located just 5 miles off the Overseas Highway. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishing. The shady screen …see more

from $100 / night

$700 / week

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from $100 / night

20

Vacation home in Summerland Key

Lower Keys / Summerland Key

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Located at mile marker 27 just across from the famous restaurant Boondocks,this is truly a rare find with all of these features. Breath taking view from every advantage point. Weather your looking out the front porch of the master bedroom at the salt water flat as the s …see more

from $300 / night

$2100 / week

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from $300 / night

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