Find Vacation Rentals in Summerland Key

We have 444 properties to choose from
Summerland Key

Popular Summerland Key Vacation Homes and Apartments

Find the perfect Summerland Key vacation accommodation

House ∙ 3 guests ∙ 1 bedroom
Summerland Key, Monroe County, Florida, United States
from $244
VRBO
4.2
Details
House ∙ 4 guests ∙ 2 bedrooms
Summerland Key, Monroe County, Florida, United States
from $251
VRBO
4.5
Details
House ∙ 6 guests ∙ 3 bedrooms
Summerland Key, Monroe County, Florida, United States
from $547
VRBO
5.0
Details
House ∙ 4 guests ∙ 2 bedrooms
Cudjoe Key, Monroe County, Florida, United States
from $213
VRBO
4.2
Details
House ∙ 4 guests ∙ 2 bedrooms
Cudjoe Key, Monroe County, Florida, United States
from $209
VRBO
4.9
Details
House ∙ 6 guests ∙ 2 bedrooms
Cudjoe Key, Monroe County, Florida, United States
from $265
VRBO
4.6
Details
House ∙ 8 guests ∙ 4 bedrooms
Summerland Key, Monroe County, Florida, United States
from $638
VRBO
5.0
Details
House ∙ 8 guests ∙ 3 bedrooms
Summerland Key, Monroe County, Florida, United States
from $566
VRBO
4.7
Details
House ∙ 6 guests ∙ 2 bedrooms
Cudjoe Key, Monroe County, Florida, United States
from $394
VRBO
4.9
Details
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Recommended Rentals With Pools

Pool
House ∙ 6 guests ∙ 2 bedrooms
Summerland Key, Monroe County, Florida, United States
from $143
VRBO
4.4
Details
Pool
House ∙ 10 guests ∙ 3 bedrooms
Summerland Key, Monroe County, Florida, United States
from $828
VRBO
5.0
Details
Pool
House ∙ 8 guests ∙ 4 bedrooms
Summerland Key, Monroe County, Florida, United States
from $369
Airbnb
5.0
Details
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Vacation Properties for Fishing

Fishing
House ∙ 8 guests ∙ 3 bedrooms
Cudjoe Key, Monroe County, Florida, United States
from $673
VRBO
5.0
Details
Fishing
House ∙ 6 guests ∙ 2 bedrooms
Cudjoe Key, Monroe County, Florida, United States
from $193
VRBO
4.0
Details
Fishing
House ∙ 8 guests ∙ 3 bedrooms
Cudjoe Key, Monroe County, Florida, United States
from $160
VRBO
5.0
Details
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Pet-Friendly Homes and Apartments

Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
Summerland Key, Monroe County, Florida, United States
from $120
VRBO
5.0
Details
Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
Summerland Key, Monroe County, Florida, United States
from $585
VRBO
5.0
Details
Pet-friendly
House ∙ 6 guests ∙ 2 bedrooms
Summerland Key, Monroe County, Florida, United States
from $121
Airbnb
5.0
Details
View more
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.

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