Summerland Key Vacation Rentals - HolidayHomes base64Hash Summerland Key Vacation Rentals - HolidayHomes

Summerland Key Vacation Rentals

Browse 133 available vacation homes and compared across 6 trusted partners

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Top-Rated Vacation rentals in Summerland Key

Book the highest-rated Summerland Key vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Summerland Key

Waterfront Beach Houses with Dock & Heated Pool!

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House Summerland Key

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

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Cabin Summerland Key

SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing and Lobster

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House Summerland Key

House with barbeque, garden & patio

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House Summerland Key

House with patio, garden & barbecue

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Cabin Summerland Key

FLAMINGO COTTAGE summer fun. Pool, boating, fishing lobster season.

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Cabin Summerland Key

Cottage with BBQ & pool

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House Summerland Key

Family-friendly pleasant house with barbecue & terrace | Perfect for remote work | Pet-friendly

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House Summerland Key

Vacation home with hot tub & barbecue

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House Summerland Key

Vacation home with private pool, garden & BBQ | Nature view

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House Summerland Key

Vacation home with private pool, terrace & barbeque | Perfect for remote work

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House Summerland Key

House with private pool, terrace & BBQ | Suitable for remote work

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House Summerland Key

Views Views! Direct Oceanfront, Beautiful Inside!

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House Summerland Key

House with garden, private pool & hot tub

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House Summerland Key

Private and Exclusive Beach Getaway

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Top 15 most Recommended Vacation Rentals in Summerland Key

Discover your ideal Summerland Key vacation rental with real-time comparisons of 133 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Summerland Key
House ∙ 16 guests ∙ 7 bedrooms

Vacation home with hot tub

Summerland Key, Monroe County, Florida, United States
Spacious house rental in Summerland Key accommodates 16 guests and allows pets for a perfect family getaway.
from $1,018
per night
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House Summerland Key
House ∙ 4 guests ∙ 2 bedrooms

House with hot tub, pool & barbecue

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 4 guests and features a hot tub for relaxing after a day of adventure.
from $444
per night
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House Summerland Key
House ∙ 12 guests ∙ 4 bedrooms

Family-friendly beautiful house with garden, barbeque & private pool | Nature view | Good for workation | Dogs allowed

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 12 guests and features a private pool for a relaxing stay.
from $777
per night
(86)
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Cabin Summerland Key
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with yard, patio & BBQ

Summerland Key, Monroe County, Florida, United States
This cozy cabin in Summerland Key accommodates 6 guests and features a waterfront view for a perfect getaway.
from $359
per night
(6)
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House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped house with yard & barbeque

Summerland Key, Monroe County, Florida, United States
Charming house rental in Summerland Key for 6 with a spacious yard perfect for outdoor activities and relaxation.
from $258
per night
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House Summerland Key
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, heated pool & jacuzzi

Summerland Key, Monroe County, Florida, United States
Charming house rental in Summerland Key for 6 guests featuring a waterfront view and a relaxing hot tub.
from $313
per night
(10)
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House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

House with BBQ, yard & private pool

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 6 guests and features a private pool for a relaxing getaway.
from $302
per night
(6)
View deal
House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly lovely vacation home with grill, private pool & terrace | Nature view | Suitable for remote work | Dogs allowed

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 8 guests and features a pool for relaxation and enjoyment.
from $456
per night
(6)
View deal
House Summerland Key
House ∙ 9 guests ∙ 3 bedrooms

Family-oriented house with yard, pool & patio | Suitable for remote work | Pets are welcome

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 9 guests and features a family-friendly kitchen for enjoyable meals together.
from $450
per night
(2)
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