Vacation Rentals in Summerland Key, Florida

46 Properties Available

Atlantic View Luxury Villa with Pool Villa
Atlantic View Luxury Villa with Pool
$983 / night
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Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West Private vacation home
Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
$960 / night
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WEEKLY Oceanfront Home-Pool, Dock-Available Weekly or Monthly. Private vacation home
WEEKLY Oceanfront Home-Pool, Dock-Available Weekly or Monthly.
$886 / night
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Oasis - Ocean view with pool and hot tub Private vacation home
Oasis - Ocean view with pool and hot tub
$845 / night
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Gorgeous 4 Bedroom 3 Bath Open Water Pool Home with great boating Private vacation home
Gorgeous 4 Bedroom 3 Bath Open Water Pool Home with great boating
$823 / night
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Summerland Breeze - Three house retreat, perfect for multiple families Private vacation home
Summerland Breeze - Three house retreat, perfect for multiple families
$800 / night
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Private Secluded Ocean View & Pool Near Key West Private vacation home
Private Secluded Ocean View & Pool Near Key West
$756 / night
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Starlight Serenity - Hideaway w Stunning Views Private vacation home
Starlight Serenity - Hideaway w Stunning Views
$735 / night
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Beautiful 3 Bedroom 3 Bath Open Water Pool Home With Excellent Boating Private vacation home
Beautiful 3 Bedroom 3 Bath Open Water Pool Home With Excellent Boating
$647 / night
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Open Water ~ Pool Home in Summerland Key Private vacation home
Open Water ~ Pool Home in Summerland Key
$625 / night
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Great Location , Great Vibes, Great Pool Private vacation home
Great Location , Great Vibes, Great Pool
$556 / night
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Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa Private vacation home
Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
$552 / night
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Waterfront House in the heart of Cudjoe Key. Private vacation home
Waterfront House in the heart of Cudjoe Key.
$550 / night
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New 3BR Ocean-Side Home on Little Torch Key, hidden gem - 28 Miles from Key West Private vacation home
New 3BR Ocean-Side Home on Little Torch Key, hidden gem - 28 Miles from Key West
$540 / night
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Sugarloaf Hideaway | Pool, Bikes, Kayaks, Paddleboards & Fishing Gear Private vacation home
Sugarloaf Hideaway | Pool, Bikes, Kayaks, Paddleboards & Fishing Gear
$519 / night
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Sea Glass House of Summerland Key! Pool, 70 feet of Seawall, deep water canal! Private vacation home
Sea Glass House of Summerland Key! Pool, 70 feet of Seawall, deep water canal!
$519 / night
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Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel Private vacation home
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
$482 / night
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Palms & Pina Coladas- 3 BR Waterfront Paradise w/ Private Pool, 80 ft Dockage Private vacation home
Palms & Pina Coladas- 3 BR Waterfront Paradise w/ Private Pool, 80 ft Dockage
$479 / night
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Open water pool home 25miles from Key West Private vacation home
Open water pool home 25miles from Key West
$460 / night
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PARADISE on Sugarloaf Key! 704-650-8105 For current details. Private vacation home
PARADISE on Sugarloaf Key! 704-650-8105 For current details.
$444 / night
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Sugarloaf Sunrise Private vacation home
Sugarloaf Sunrise
$409 / night
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Serene Beautiful Open Water with dockage. Private vacation home
Serene Beautiful Open Water with dockage.
$402 / night
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Sunset Views, oceanfront Private vacation home
Sunset Views, oceanfront
$389 / night
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Large 5 Bedroom Canal Home in Summerland Key, FL with Pool Private vacation home
Large 5 Bedroom Canal Home in Summerland Key, FL with Pool
$378 / night
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NAUTICAL NEST - 3-bedroom canal front tranquil home on Summerland Key with AC Private vacation home
NAUTICAL NEST - 3-bedroom canal front tranquil home on Summerland Key with AC
$358 / night
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Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views! Private vacation home
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
$329 / night
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House, relaxing space,waterfront at Cudjoe Key Private vacation home
House, relaxing space,waterfront at Cudjoe Key
$326 / night
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Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool! Private vacation home
Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool!
$325 / night
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Dickey's Dockside Retreat Private vacation home
Dickey's Dockside Retreat
$316 / night
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Florida keys Waterfront,Forever Summer Private vacation home
Florida keys Waterfront,Forever Summer
$313 / night
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Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water Private vacation home
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
$307 / night
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Sunset Beach, 4 bedroom, 5.5 bath, oceanfront home! Private vacation home
Sunset Beach, 4 bedroom, 5.5 bath, oceanfront home!
$292 / night
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Lower Keys Paradise KW Private vacation home
Lower Keys Paradise KW
$286 / night
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3\/2 on the Water in Paradise Monthly Rental 28 Day min. Private vacation home
3\/2 on the Water in Paradise Monthly Rental 28 Day min.
$272 / night
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Bahama Breeze in the Keys Private vacation home
Bahama Breeze in the Keys
$272 / night
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Oceanfront home with 2 kayaks, 2 bikes, deck, ocean views, grill, washer\/dryer Private vacation home
Oceanfront home with 2 kayaks, 2 bikes, deck, ocean views, grill, washer\/dryer
$255 / night
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2 Bedroom\/3 Bath Waterfront 28 day rental Private vacation home
2 Bedroom\/3 Bath Waterfront 28 day rental
$244 / night
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Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, Dockage & Dog-Friendly Private vacation home
Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, Dockage & Dog-Friendly
$220 / night
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The Bent Anchor-boat lift diving snorkeling fishing key deer 22 miles Key West Private vacation home
The Bent Anchor-boat lift diving snorkeling fishing key deer 22 miles Key West
$209 / night
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Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly Private vacation home
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
$207 / night
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Special Rate Available August 2026 book now Private vacation home
Special Rate Available August 2026 book now
$204 / night
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Kelly's Kabin - Adorable Private Summerland Key Cottage Private vacation home
Kelly's Kabin - Adorable Private Summerland Key Cottage
$200 / night
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Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry Private vacation home
Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
$183 / night
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The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17 Private vacation home
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17
$165 / night
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Gorgeous Canal Front Home! Come stay at 'Casa Key Ramrod' Private vacation home
Gorgeous Canal Front Home! Come stay at 'Casa Key Ramrod'
$150 / night
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Little Palm Island Resort & Spa - A Noble House Resort Hotel resort
Little Palm Island Resort & Spa - A Noble House Resort
$0 / night
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