15 Best Summerland Key Vacation rentals on Holiday Lettings - House rentals

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120 Vacation rentals

(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

18

Summerland Key Vacation home rental

Lower Keys / Summerland Key

3 9 28 nights min

  • 3 bedrooms
  • Sleeps 9
  • 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. Heated POOL with separate bath, 10K Boat lift, Totally remodeled (2017) waterfront home. Will accommodate 9 people very comfortably. This is a charming way to spend your vacation. A Large de …see more

from $150 / night

$1,050 - $1,260 / week

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from $150 / 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

(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

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

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

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
  • Pet friendly
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

$1,176 / week

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from $168 / 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 two-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 v …see more

from $152 / night

$1,064 / week

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Responds fast!
avg. 2 hours 1 minutes

from $152 / 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

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
  • Pet friendly
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

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

$1,400 / 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
  • Pet friendly
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

$1,867 / week

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from $267 / 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

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

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

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
  • Pet friendly
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

$1,400 / 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
  • Pet friendly
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

$1,447 / week

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from $207 / night

21

Summerland Key Vacation home rental

Lower Keys / Summerland Key

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Vacation home sits behind some mangroves and has a view over Cudjoe Bay to the Atlantic. 4 bedroom and 2 bathrooms. Large deck with water access for a small boat. Water access has a shallow area to and from the deep area the boat would be docked at. Vacation home sits f …see more

from $329 / night

$2,300 - $2,600 / week

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from $329 / 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