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

Summerland Key Vacation Rentals

Browse 154 available vacation homes and compared across 7 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
Starfish Cottage - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
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Cabin Summerland Key
FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
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House Summerland Key
House with barbeque, garden & patio | Nature view
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House Summerland Key
House with patio, garden & barbecue
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House Summerland Key
Vacation home with patio, BBQ & private pool
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Cabin Summerland Key
SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!
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House Summerland Key
House with patio, barbecue & private 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 barbeque & terrace
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House Summerland Key
House with private pool, terrace & BBQ | Suitable for remote work
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House Summerland Key
New pool & Huge master suite! Open water views, 2 stories of wrap around decks
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House Summerland Key
House with garden, private pool & hot tub
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House Summerland Key
Family-oriented big house with terrace, private pool & garden | Good for workation | Pets are welcome
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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 154 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Summerland Key
House ∙ 10 guests ∙ 3 bedrooms

100 m² House

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 10 guests and features a private pool for a relaxing getaway.
from $196
per night
(2)
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House Summerland Key
16 guests ∙ 7 bedrooms

House

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 $1,091
per night
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House Summerland Key
6 guests ∙ 2 bedrooms

House

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 6 guests and features a private pool for relaxation and enjoyment.
from $161
per night
(2)
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House Summerland Key
House ∙ 14 guests ∙ 5 bedrooms

331 m² House

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 14 guests and features a private pool for a relaxing getaway.
from $795
per night
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House Summerland Key
4 guests ∙ 2 bedrooms

House

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 $403
per night
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House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

76 m² House

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 $244
per night
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House Summerland Key
12 guests ∙ 4 bedrooms

House

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 $931
per night
(83)
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House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

232 m² House

Summerland Key, Monroe County, Florida, United States
Spacious house rental in Summerland Key accommodates 6 guests and features a private pool for relaxation and enjoyment.
from $238
per night
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House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

104 m² House

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 8 guests and features a waterfront location with a family-friendly atmosphere.
from $494
per night
(30)
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