Summerland Key Holiday Rentals
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5 mi
136 rentals in Summerland Key.
Private Secluded Ocean View & Pool Near Key West
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SEA SHELL COTTAGE UNIT #2
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FLAMINGO COTTAGE UNIT #1
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Beachside * Torchview Waterfront Retreat
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PALM COTTAGE
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Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
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Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
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20 ft from your room to a clean canal full of fish and lobsters and crabs.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
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Love Shack | Charming 2 bed/1 bath cottage on Summerland Key
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock
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Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!
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Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe
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Walk to the Pool - Venture Out Unit 333
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Beach Bliss, Oceanfront with pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunshine 23 | Dog-friendly 2 bed/2 bath canalfront boating home on Cudjoe Key
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Oceanfront house private beach & protected canal dockage for up to 36' boat
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Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Keys cottage, oceanfront, dock, private, great location, fenced backyard
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Dickey's Dockside Retreat
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Waterfront House in the heart of Cudjoe Key.
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Beautiful Lagoon view on canal pool home Summerland
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Home With Large Private Deck with boat dockage
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Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home
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Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Vacation like a local
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November 2024 special rate! Fisherman’s paradise! Ice machine, bait freezer, etc
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Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock
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Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key
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Tarpon Canal | Nearly new 3 bed/2 bath home with canal views on Ramrod Key
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Captain House with Boat Basin & Ramp!
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Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key
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Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple
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Waterfront beach house with boat ramp
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Stylish & Modern Summerland Key Private Retreat!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bungalows at Sugarloaf Beach - Mi Azucar
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September Special Rate! Book Now at this canal front pool home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe
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Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key
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Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28
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Florida Keys Paradise!
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Reel Caribbean Getaway
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
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Oasis - Ocean view with pool and hot tub
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Mariners Cove - The Kraken House
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Great Location , Great Vibes, Great Pool
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Open Water ~ Pool Home in Summerland Key
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Open Water Modern Home 2/2
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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L' archipel | Canalfront 2 bedroom retreat on Ramrod Key with brand new dock!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 136
Frequently Asked Questions about Summerland Key
- Yes, here are some popular holiday rentals in Summerland Key that have a pool:See all holiday rentals with a pool in Summerland Key on Tripadvisor
- Yes, here are some popular holiday rentals in Summerland Key that have internet access:See all holiday rentals in Summerland Key on Tripadvisor
- The best pet friendly rentals in Summerland Key are:See all pet friendly holiday rentals in Summerland Key on Tripadvisor
- Some of the most popular kid friendly rentals in Summerland Key are:See all kid friendly holiday rentals in Summerland Key on Tripadvisor
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