Summerland Key Vacation Rentals
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0+ rooms, 2+ guests
Distance from
1 mi
Price per night
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$1,000+
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38 rentals in Summerland Key.
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Cayo Villa
3 bedrooms
3 bathrooms
Sleeps 6
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Blue Lagoon
3 bedrooms
3 bathrooms
Sleeps 6
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Cove Isles
2 bedrooms
2 bathrooms
Sleeps 4
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Cruikshank
3 bedrooms
3 bathrooms
Sleeps 6
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Casa Turquesa
3 bedrooms
2 bathrooms
Sleeps 6
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Paradise Palms
3 bedrooms
2 bathrooms
Sleeps 6
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1 other traveler has booked this property
Big Torch Retreat
3 bedrooms
2 bathrooms
Sleeps 6
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Family Friendly House In Paradise
5 bedrooms
3 bathrooms
Sleeps 8
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1 other traveler has booked this property
++++PERFECT KEYS POOL HOME, MINUTES TO KEY WEST, CONVENIENT TO EVERYTHING++++
3 bedrooms
4 bathrooms
Sleeps 6
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The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17
2 bedrooms
2 bathrooms
Sleeps 6
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Ocean Front Access - Sunrise View - Fishing - Snorkeling - Pet Friendly - Unit 1
1 bedroom
1 bathroom
Sleeps 3
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30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.
2 bedrooms
2 bathrooms
Sleeps 6
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2 other travelers have booked this property
Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like
5 bedrooms
5 bathrooms
Sleeps 10
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Oceanfront House
3 bedrooms
3 bathrooms
Sleeps 8
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Blue vacation home, water front, boat dock, heated private Pool.
4 bedrooms
2 bathrooms
Sleeps 8
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3 other travelers have booked this property
Gone Fishing
3 bedrooms
2 bathrooms
Sleeps 6
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3/2 on the Water in Paradise Monthly Rental 28 Day min.
3 bedrooms
2 bathrooms
Sleeps 6
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Salty Retreat
3 bedrooms
3 bathrooms
Sleeps 8
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Hogfish Hideout
3 bedrooms
2 bathrooms
Sleeps 8
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Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards
4 bedrooms
3 bathrooms
Sleeps 10
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New listing! Incredible oceanfront home on large lot w/bar, dock & amazing views
4 bedrooms
3 bathrooms
Sleeps 13
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Mariner's Cove In The Florida Keys
5 bedrooms
4 bathrooms
Sleeps 14
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Canal Front - Recently Renovated And Very Clean Throughout :)
3 bedrooms
1 bathroom
Sleeps 6
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Kelly's Kabin private cottage on Summerland Key
1 bedroom
1 bathroom
Sleeps 5
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Oceanfront Sunsets in the Florida Keys
4 bedrooms
6 bathrooms
Sleeps 10
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BRAND NEW WATERFRONT 3/2
3 bedrooms
2 bathrooms
Sleeps 8
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Mermaid's Tale
4 bedrooms
3 bathrooms
Sleeps 8
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Isle Be Back!
4 bedrooms
2 bathrooms
Sleeps 8
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Caribbean Dream
4 bedrooms
3 bathrooms
Sleeps 10
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Keys Life
3 bedrooms
3 bathrooms
Sleeps 8
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Dog-friendly resort community home w/ shared pool, hot tub, & tennis court!
2 bedrooms
2 bathrooms
Sleeps 6
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The Pointe
2 bedrooms
2 bathrooms
Sleeps 4
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Spacious duplex w/ocean views, shared hot tub, furnished deck area, & more!
4 bedrooms
4 bathrooms
Sleeps 12
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Charming waterfront home w/ a shared hot tub, balcony, & boat dock!
2 bedrooms
2 bathrooms
Sleeps 6
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New listing! Canal front home with dock, quick ocean access and a hot tub!
2 bedrooms
2 bathrooms
Sleeps 6
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Sailfish Manor
3 bedrooms
2 bathrooms
Sleeps 9
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Villa and guest house with private pool, central AC, internet, and washer/dryer
6 bedrooms
5 bathrooms
Sleeps 16
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Bright, spacious home with private pool, internet, private washer/dryer, & loft!
4 bedrooms
4 bathrooms
Sleeps 12
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