Summerland Key Vacation Rentals
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116 rentals in Summerland Key.
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Kelly’s Kabin - Adorable Private Summerland Key Cottage
Rental Home
1 bedroom
1 bathroom
Sleeps 5
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Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
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Ocean Front Modern Home
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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Oceanfront Sunsets in the Florida Keys
Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
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Banana Cabana, Canal Front Home Sugarloaf Key Mm 17
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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LIVING IN BEAUTIFUL PARADISE
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Acreage Beach House w/ Pool & Billiards
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Canal Front With Easy Access To Atlantic Or Gulf
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Pool Home on Tranquil Private Cruikshank Island
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Ocean Front Access - Sunrise View - Fishing - Snorkeling - Pet Friendly - Unit 1
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Charming and Private
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
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Cudjoe Gardens Estate With Ocean View & Pool
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
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Blue Pearl of Summerland Key
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers
Rental Home
8 bedrooms
7 bathrooms
Sleeps 20
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Blue vacation home, water front, boat dock, heated private Pool.
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Blackbeard`s Hideaway
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Reel Caribbean Getaway
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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2 Bedroom/3 Bath Waterfront 28 day rental
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
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2 bedroom accommodation in Summerland Key
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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Salty Retreat
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Casa Turquesa
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Hogfish Hideout
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Waterfront, two-story house w/private outdoor pool, poolside grill, boat access
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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TARPON RANCH - Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock
Rental Home
6 bedrooms
8 bathrooms
Sleeps 14
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New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa
Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
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Blue Lagoon
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
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Villa Cayo
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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The Helms House
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Keys Life
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Cruikshank
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Sailfish Manor
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
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Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
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The Pointe
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Paradise in the Keys
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Cove Isles
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Reel Paradise
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Lower Keys Waterfront Getaway
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Summerland Nest - Oceanfront with pool
Rental Home
7 bedrooms
5 bathrooms
Sleeps 12
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BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do
Rental Home
2 bedrooms
2 bathrooms
Sleeps 13
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Sunny Lei is a home with lots of amenities and great location.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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TARPON RANCH - Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock
Rental Home
7 bedrooms
7 bathrooms
Sleeps 14
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THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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