Vacation Rentals in Summerland Key, FL: Compare 10+ Sites & Save

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586 Best Vacation Rentals in Summerland Key (Starting from $150)

Summerland Canal
Summerland Canal
House
Summerland Key, FL, USA
0.2k from Summerland Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms5 Guests
New to Booking
$160
Average price / night
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Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
House
Summerland Key, FL, 33042, United States
0.2k from Summerland Key center

2 Bedrooms5 Guests
New to Booking
$198
Average price / night
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Skyway Living
Skyway Living
House
Summerland Key, FL, USA
0.5k from Summerland Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

2 Bedrooms6 Guests
New to Booking
$237
Average price / night
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Relax at the flying hogfish
Relax at the flying hogfish
House
Summerland Key, FL, 33042, United States
0.2k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.6

Exceptional

14 reviews

$232
Average price / night
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Love Shack
Love Shack
House
Summerland Key, FL, USA
1.5k from Summerland Key center

Barbecue/Outdoor Cooking, Internet, Security/Safety, Laundry, Child Friendly

2 Bedrooms4 Guests
New to Booking
$150
Average price / night
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Ground Level Home With Deepwater Canal
Ground Level Home With Deepwater Canal
House
Summerland Key, FL, 33042, United States
0.3k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$193
Average price / night
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Turtle Cove Views by Last Key Realty
Turtle Cove Views by Last Key Realty
House
Cudjoe Key, FL, USA
2.5k from Summerland Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
7.0

Good

1 reviews

$513
Average price / night
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Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
House
Summerland Key, FL, 33042, United States
0.4k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$530
Average price / night
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Tidewater Views by Last Key Realty
Tidewater Views by Last Key Realty
House
Cudjoe Key, FL, USA
2.5k from Summerland Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$424
Average price / night
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  Summerland Airport Hangar Home with Pool, Private Runway and deep wide Canal
Summerland Airport Hangar Home with Pool, Private Runway and deep wide Canal
House
Summerland Key, FL, 33042, United States
0.4k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
New to Booking
$359
Average price / night
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Island Oasis ~ YOUR Paradise Awaits!
Island Oasis ~ YOUR Paradise Awaits!
House
Summerland Key, Florida, USA
2.5k from Summerland Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms6 Guests
7.4

Good

5 reviews

$386
Average price / night
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Summerland Serenity  Elevated Waterfront Luxury with Private Elevator & Pool
Summerland Serenity Elevated Waterfront Luxury with Private Elevator & Pool
House
Summerland Key, FL, 33042, United States
0.4k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

5 Bedrooms12 Guests
New to Booking
$508
Average price / night
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OCEANIA. water front cottage retreat ~
OCEANIA. water front cottage retreat ~
Villa
Cudjoe Key, FL, USA
2.6k from Summerland Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms6 Guests
9.4

Superb

16 reviews

$826
Average price / night
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Ocean Front Modern Home
Ocean Front Modern Home
House
Summerland Key, FL, 33042, United States
0.4k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms9 Guests
10.0

Exceptional

18 reviews

$497
Average price / night
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NAUTILUS.ocean front cottage retreat ~
NAUTILUS.ocean front cottage retreat ~
Villa
Cudjoe Key, FL, USA
2.6k from Summerland Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms6 Guests
9.2

Superb

16 reviews

$908
Average price / night
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Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
House
Summerland Key, FL, 33042, United States
0.4k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$291
Average price / night
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Pelican's Roost, Waterfront comfort at Venture Out
Pelican's Roost, Waterfront comfort at Venture Out
House
Cudjoe Key, FL, USA
2.7k from Summerland Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms5 Guests
9.2

Superb

15 reviews

$303
Average price / night
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Waterfront home with boat/canal access, screened lanai, & renovated interior
Waterfront home with boat/canal access, screened lanai, & renovated interior
House
Summerland Key, FL, 33042, United States
0.5k from Summerland Key center

3 Bedrooms6 Guests
New to Booking
$519
Average price / night
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Dock Holiday
Dock Holiday
House
Cudjoe Key, FL, USA
2.7k from Summerland Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay

2 Bedrooms4 Guests
7.6

Good

5 reviews

$293
Average price / night
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Canalfront house with private pool, WiFi, private washer/dryer, and central AC
Canalfront house with private pool, WiFi, private washer/dryer, and central AC
House
Summerland Key, FL, 33042, United States
0.5k from Summerland Key center

2 Bedrooms6 Guests
New to Booking
$302
Average price / night
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Mermaid Magic by Last Key Realty
Mermaid Magic by Last Key Realty
House
Cudjoe Key, FL, USA
2.7k from Summerland Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$875
Average price / night
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Oceanfront Sunsets in the Florida Keys
Oceanfront Sunsets in the Florida Keys
House
Summerland Key, FL, 33042, United States
0.5k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$472
Average price / night
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Sunset Serenity – 3BR Open Water Oasis On Summerland Key Boat Dockage, Stunning Views & Pet Friendly
Sunset Serenity – 3BR Open Water Oasis On Summerland Key Boat Dockage, Stunning Views & Pet Friendly
House
Summerland Key, FL, 33042, United States
0.6k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$441
Average price / night
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Mariners Cove - The Kraken House
Mariners Cove - The Kraken House
House
Summerland Key, FL, 33042, United States
0.6k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
9.8

Exceptional

9 reviews

$698
Average price / night
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Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
House
Summerland Key, FL, 33042, United States
0.6k from Summerland Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms10 Guests
8.0

Good

1 reviews

$374
Average price / night
Check Availability
Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key Cottage
House
Summerland Key, FL, 33042, United States
0.6k from Summerland Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms5 Guests
9.8

Exceptional

123 reviews

$531
Average price / night
Check Availability
Views Views!  Direct Oceanfront, Beautiful Inside!
Views Views! Direct Oceanfront, Beautiful Inside!
House
Summerland Key, FL, 33042, United States
0.7k from Summerland Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$355
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Summerland Key.

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Frequently Asked Questions

You can explore 586 verified vacation rentals in Summerland Key. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Summerland Key vary depending on the season, property size, and location. Rates typically start from around $150 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Summerland Key include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Summerland Key welcome pets. Currently, 42 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Summerland Key often include amenities such as Wellness Facilities, Pool, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.