Find Vacation Rentals in Summerland Key

Summerland Key
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Popular Summerland Key Vacation Rentals

Find the perfect Summerland Key vacation rental

Cottage Summerland Key
e.g. 6/17 - 6/24 (Fri - Fri)
$629 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
4.0
"Very good" (1 rating)
Summerland Key, Monroe County, Florida, United States
Details
Vacasa
Details
House Summerland Key
e.g. 1/21 - 1/28 (Sat - Sat)
$804 per night
House ∙ 8 guests ∙ 3 bedrooms
Summerland Key, Monroe County, Florida, United States
Free cancellation
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FlipKey
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House Summerland Key
e.g. 10/15 - 10/22 (Sat - Sat)
-30%
$534
$372 per night
House ∙ 4 guests ∙ 2 bedrooms
Summerland Key, Monroe County, Florida, United States
Free cancellation
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FlipKey
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House Summerland Key
e.g. 8/27 - 9/3 (Sat - Sat)
$909 per night
House ∙ 14 guests ∙ 5 bedrooms
4.8
"Excellent" (12 ratings)
Summerland Key, Monroe County, Florida, United States
Free cancellation
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FlipKey
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House Summerland Key
e.g. 8/27 - 9/3 (Sat - Sat)
$680 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (1 rating)
Summerland Key, Monroe County, Florida, United States
Free cancellation
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FlipKey
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House Summerland Key
e.g. 4/22 - 4/29 (Sat - Sat)
$758 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (3 ratings)
Summerland Key, Monroe County, Florida, United States
Details
FlipKey
Details
House Summerland Key
e.g. 9/10 - 9/17 (Sat - Sat)
-38%
$2,084
$1,290 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
"Excellent" (1 rating)
Summerland Key, Monroe County, Florida, United States
Details
Vacasa
Details
Motel Summerland Key
e.g. 8/27 - 9/3 (Sat - Sat)
$213 per night
Motel ∙ 4 guests ∙ 1 bedroom
Summerland Key, Monroe County, Florida, United States
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HomeToGo
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House Summerland Key
e.g. 5/21 - 5/28 (Sat - Sat)
$784 per night
House ∙ 12 guests ∙ 5 bedrooms
4.8
"Excellent" (10 ratings)
Summerland Key, Monroe County, Florida, United States
Details
Florida Rental By Owners
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Vacation rentals and apartments with air conditioning

House Aircondition Summerland Key
e.g. 12/3 - 12/10 (Sat - Sat)
-31%
$1,003
$694 per night
House ∙ 10 guests ∙ 5 bedrooms
4.5
"Outstanding" (1 rating)
Summerland Key, Monroe County, Florida, United States
Aircondition
Details
Vacasa
Details
House Aircondition Summerland Key
e.g. 1/14 - 1/21 (Sat - Sat)
-57%
$6,306
$2,710 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (17 ratings)
Summerland Key, Monroe County, Florida, United States
Aircondition
Details
Vacasa
Details
House Aircondition Summerland Key
e.g. 8/20 - 8/27 (Sat - Sat)
-43%
$3,976
$2,261 per night
House ∙ 20 guests ∙ 8 bedrooms
4.3
"Very good" (7 ratings)
Summerland Key, Monroe County, Florida, United States
Aircondition
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Vacasa
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Apartments and vacation rentals with a kitchen

House Kitchen Summerland Key
e.g. 10/8 - 10/15 (Sat - Sat)
$295 per night
House ∙ 6 guests ∙ 1 bedroom
4.2
"Very good" (23 ratings)
Summerland Key, Monroe County, Florida, United States
Kitchen
Details
Vacasa
Details
House Kitchen Summerland Key
e.g. 9/10 - 9/17 (Sat - Sat)
-42%
$651
$380 per night
House ∙ 4 guests ∙ 2 bedrooms
4.4
"Very good" (5 ratings)
Summerland Key, Monroe County, Florida, United States
Kitchen
Details
Vacasa
Details
House Kitchen Summerland Key
e.g. 5/21 - 5/28 (Sat - Sat)
$756 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (10 ratings)
Summerland Key, Monroe County, Florida, United States
Kitchen
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FlipKey
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Vacation homes and cottages with a garden

Motel Yard Summerland Key
e.g. 9/10 - 9/17 (Sat - Sat)
-55%
$448
$203 per night
Motel ∙ 14 guests ∙ 1 bedroom
4.4
"Very good" (2025 ratings)
Summerland Key, Monroe County, Florida, United States
Free cancellation
Yard
Details
Expedia
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Motel Yard Summerland Key
e.g. 8/27 - 9/3 (Sat - Sat)
$213 per night
Motel ∙ 2 guests ∙ 1 bedroom
Summerland Key, Monroe County, Florida, United States
Yard
Details
HomeToGo
Details
House Yard Summerland Key
e.g. 8/27 - 9/3 (Sat - Sat)
$917 per night
House ∙ 14 guests ∙ 6 bedrooms
4.5
"Outstanding" (16 ratings)
Summerland Key, Monroe County, Florida, United States
Yard
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FlipKey
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Frequently Asked Questions

What is the price of vacation rentals in Summerland Key?

Usually, a stay in Summerland Key starts at $167 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 64 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

What are the trendiest neighborhoods Summerland Key?

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