Find Vacation Rentals in Summerland Key

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Popular Summerland Key Vacation Rentals

Find the perfect Summerland Key vacation rental

House Summerland Key
from $250 per night
House ∙ 8 guests ∙ 3 bedrooms

149 m² House

4.8
Outstanding(62 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
Cottage Summerland Key
from $265 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

45 m² Cottage

5.0
Outstanding(52 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
House Summerland Key
from $365 per night
8 guests ∙ 4 bedrooms

House

4.5
Excellent(8 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
House Summerland Key
from $769 per night
12 guests ∙ 4 bedrooms

House

4.6
Excellent(65 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
House Summerland Key
from $1,080 per night
House ∙ 20 guests ∙ 8 bedrooms

316 m² House

5.0
Outstanding(82 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
House Summerland Key
from $217 per night
4 guests ∙ 1 bedroom

House

4.9
Outstanding(54 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
House Summerland Key
from $231 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(8 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
House Summerland Key
from $877 per night
14 guests ∙ 7 bedrooms

House

4.5
Excellent(4 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
Cottage Summerland Key
from $350 per night
Cottage ∙ 8 guests ∙ 2 bedrooms

139 m² Cottage

4.7
Excellent(28 ratings)
Summerland Key, Monroe County, Florida, United States
Vrbo
Details
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Recommended Rentals With Pools

House  Summerland Key
from $543 per night
House ∙ 9 guests ∙ 4 bedrooms

158 m² House

5.0
Outstanding(4 ratings)
Summerland Key, Monroe County, Florida, United States
Pool
Vrbo
Details
House  Summerland Key
from $499 per night
House ∙ 9 guests ∙ 4 bedrooms

257 m² House

5.0
Outstanding(26 ratings)
Summerland Key, Monroe County, Florida, United States
Pool
Vrbo
Details
House  Summerland Key
from $576 per night
14 guests ∙ 6 bedrooms

House

5.0
Outstanding(8 ratings)
Summerland Key, Monroe County, Florida, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Summerland Key
from $484 per night
6 guests ∙ 3 bedrooms

House

4.8
Outstanding(67 ratings)
Summerland Key, Monroe County, Florida, United States
Pet-friendly
Vrbo
Details
House  Summerland Key
from $322 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(15 ratings)
Summerland Key, Monroe County, Florida, United States
Pet-friendly
Vrbo
Details
Cottage  Summerland Key
from $199 per night
2 guests ∙ 1 bedroom

Cottage

4.7
Excellent(20 ratings)
Summerland Key, Monroe County, Florida, United States
Pet-friendly
Vrbo
Details
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Vacation rentals with a balcony

House  Summerland Key
from $326 per night
House ∙ 6 guests ∙ 2 bedrooms

120 m² House

5.0
Outstanding(5 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
Vacasa
Details
House  Summerland Key
from $371 per night
House ∙ 8 guests ∙ 4 bedrooms

149 m² House

5.0
Outstanding(36 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
Vrbo
Details
House  Summerland Key
from $334 per night
House ∙ 8 guests ∙ 4 bedrooms

144 m² House

Summerland Key, Monroe County, Florida, United States
Balcony
Vrbo
Details
Show more

Frequently Asked Questions

What is the price of vacation rentals in Summerland Key?

Usually, a stay in Summerland Key starts at $168 per night.

Are there any vacation rentals available to book in Summerland Key?

Our large collection of vacation homes makes it easy to filter and compare 259 offers in Summerland Key.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Summerland Key

Find the best Summerland Key vacation rentals on Tripping.com. With over 77 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Summerland Key range from $71 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 73 homes in Summerland Key offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 38 rentals with pool or jacuzzi, or relax with the family in one of the 75 homes with cable TV. For all those pet owners with dogs or cats, Summerland Key offers 31 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 5 vacation rental sites in Summerland Key where the top providers in that area are HomeAway, TripAdvisor, and VacationRentals. There are 45 HomeAway rentals, 22 TripAdvisor short term rentals and 4 VacationRentals vacation rentals.

Popular Day Trips Near Summerland Key

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