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  •  Pool Home on Tranquil Private Cruikshank Island available for MARCH 2024!!
    From $300 per night (USD)

    VRBO

    Pool Home on Tranquil Private Cruikshank Island available for MARCH 2024!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private is ...

    From $300 per night (USD)

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    Details
  • Kelly's Kabin - Adorable Private Summerland Key Cottage
    From $200 per night (USD)

    Expedia

    Kelly's Kabin - Adorable Private Summerland Key Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...

    From $200 per night (USD)

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    Details
  • Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
    From $175 per night (USD)

    VRBO

    Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Amazing canal front 3 bed 3 bath open concept house located in prestigious community of Summerland Key Cove. It is the ...

    From $175 per night (USD)

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    Details
  • One of the very few beach houses with a daily, rental license in the Keys.
    From $599 per night (USD)

    Expedia

    One of the very few beach houses with a daily, rental license in the Keys.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    This is a newly remodeled four bedrooms elegant house. The property has its own private beach located in the heart of Su ...

    From $599 per night (USD)

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    Details
  • Summerland Cove Paradise Waterfront Deep Water Canal
    From $198 per night (USD)

    VRBO

    Summerland Cove Paradise Waterfront Deep Water Canal

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    3 Bed 2 bath Florida Keys home. In need of a serene getaway with the ocean at arms reach? This 3 bedroom, 2 bathroom hom ...

    From $198 per night (USD)

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  • The Tiki: Canalfront retreat w/ pool
    From $322 per night (USD)

    Expedia

    The Tiki: Canalfront retreat w/ pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy your winter in paradise at this perfectly appointed pool home on a clear, deep boating canal on Summerland Key. Up ...

    From $322 per night (USD)

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    Details
  • Ocean Front Modern Home
    From $426 per night (USD)

    VRBO

    Ocean Front Modern Home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    This luxurious cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands ...

    From $426 per night (USD)

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  • Latitude Adjustment: Canalfront, hot tub
    From $199 per night (USD)

    Expedia

    Latitude Adjustment: Canalfront, hot tub

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    3 bedroom/2 bathroom canalfront home on Summerland Key just a few homes in from open water. Vaulted ceilings, updated an ...

    From $199 per night (USD)

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    Details
  • Kiki’s Casa: Beautifully Updated Canal Front Home, Pool & Dockage, Quick Access to Atlantic or Gulf!
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    Kiki’s Casa: Beautifully Updated Canal Front Home, Pool & Dockage, Quick Access to Atlantic or Gulf!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Kiki's Casa - Your Beautifully Updated Canal Front Retreat in the Florida Keys! Discover the ultimate vacation experienc ...

    Click For Pricing

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  • Forever Summer
    From $289 per night (USD)

    Expedia

    Forever Summer

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Waterfront house with heated pool. Located on the canal of Summerland Ke ...

    From $289 per night (USD)

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  • Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry!
    From $126 per night (USD)

    VRBO

    Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Summerland Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...

    From $126 per night (USD)

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  • Canalfront House with Private Pool, WiFi, Private Washer\/Dryer, and Central AC
    From $223 per night (USD)

    Expedia

    Canalfront House with Private Pool, WiFi, Private Washer\/Dryer, and Central AC

    Bedrooms:
    4
    Bathrooms:
    2
    Sleeps:
    6

    Skyway Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $223 per night (USD)

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  • Summerland Breeze - Three house retreat, perfect for multiple families
    From $1000 per night (USD)

    VRBO

    Summerland Breeze - Three house retreat, perfect for multiple families

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    14

    Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property ...

    From $1000 per night (USD)

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  • Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple Families, Dogs OK!
    From $345 per night (USD)

    Expedia

    Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple Families, Dogs OK!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Welcome to "Anchors Aweigh," your passport to the ultimate oceanfront retreat on the tranquil shores of Summerland Key. ...

    From $345 per night (USD)

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  • Tropical Island Sanctuary
    From $152 per night (USD)

    VRBO

    Tropical Island Sanctuary

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our beautiful tropical island retreat! Enjoy all the the splendor the lower Keys have to offer from our home ...

    From $152 per night (USD)

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  • Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
    From $215 per night (USD)

    Expedia

    Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to 'Lake It Easy' – Your Canal Front Oasis on Summerland Key! Indulge in the laid-back Florida Keys lifestyle in ...

    From $215 per night (USD)

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  • Emerald Seas - Florida Keys Ocean Front Paradise!
    From $459 per night (USD)

    VRBO

    Emerald Seas - Florida Keys Ocean Front Paradise!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal ...

    From $459 per night (USD)

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    Details
  • Blue Lagoon paradise. \nRare point house with 230 ft surrounded by water …
    From $415 per night (USD)

    Expedia

    Blue Lagoon paradise. \nRare point house with 230 ft surrounded by water …

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    7

    If you’re looking for a coastal experience with a modern peaceful clean stay this home is for you. Stay comfortably in S ...

    From $415 per night (USD)

    Expedia

    Details
  • Beach Bliss, Oceanfront with pool
    From $550 per night (USD)

    VRBO

    Beach Bliss, Oceanfront with pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beach Bliss has everything you need for a spectacular vacation. The views inside and outside the home are mesmerizing. T ...

    From $550 per night (USD)

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  • LIVING IN BEAUTIFUL PARADISE
    From $189 per night (USD)

    VRBO

    LIVING IN BEAUTIFUL PARADISE

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy the view from the large porch overlooking a deep, wide, crystal blue, clear canal with quick boating access to bot ...

    From $189 per night (USD)

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  • Open water pool home 25miles from Key West
    From $395 per night (USD)

    VRBO

    Open water pool home 25miles from Key West

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Relax by the pool with heater/chiller, jets and sundeck. Over 100' of seawall on deep water. Kayaks on-site. Second flo ...

    From $395 per night (USD)

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    Details
  • Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
    From $578 per night (USD)

    VRBO

    Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to this Florida Keys gem, The Blue Pearl. The Blue Pearl is a beautiful, updated waterfront home with pool in a ...

    From $578 per night (USD)

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    Details
  • Oceanfront house w\/private beach & protected canal dockage for up to 36' boat
    From $250 per night (USD)

    VRBO

    Oceanfront house w\/private beach & protected canal dockage for up to 36' boat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerl ...

    From $250 per night (USD)

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    Details
  • Luxurious, Private, Oceanfront, Gated Home
    From $960 per night (USD)

    VRBO

    Luxurious, Private, Oceanfront, Gated Home

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    12

    Stunning 1 acre oceanfront gated estate with lush landscaping, beach and extreme privacy due to the adjacent wildlife re ...

    From $960 per night (USD)

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    Details
  • Oceanfront Sunsets in the Florida Keys
    From $375 per night (USD)

    VRBO

    Oceanfront Sunsets in the Florida Keys

    Bedrooms:
    6
    Bathrooms:
    4
    Sleeps:
    8

    FOLSOM'S FOLLY... Summerland Key, Florida Interesting architecture with breezy views of the water. All rooms beautiful ...

    From $375 per night (USD)

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    Details
  • Canal Front  (Deep Water)  Tropical Villa
    From $220 per night (USD)

    VRBO

    Canal Front (Deep Water) Tropical Villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in ...

    From $220 per night (USD)

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  • Mariners Cove - The Kraken House
    From $600 per night (USD)

    VRBO

    Mariners Cove - The Kraken House

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Mariner's Cove is a private island oasis. Featuring 5 large guest rooms, 3 full bathrooms and 2 1/2 bathrooms, Gourmet C ...

    From $600 per night (USD)

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    Details
  • Relax at the flying hogfish
    From $175 per night (USD)

    VRBO

    Relax at the flying hogfish

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Located on beautiful Summerland Key, this is the perfect vacation home for any family. Just 20 minutes from Key West an ...

    From $175 per night (USD)

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    Details
  • Spectacular sunsets and open water views at this 3 BR 3 BA
    From $420 per night (USD)

    VRBO

    Spectacular sunsets and open water views at this 3 BR 3 BA

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Spectacular sunsets and open water views at this 3 BR 3 BA home on Summerland Key. Brand new dock for your large boat ...

    From $420 per night (USD)

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    Details
  • Views Views!  Direct Oceanfront, Beautiful Inside!
    From $280 per night (USD)

    VRBO

    Views Views! Direct Oceanfront, Beautiful Inside!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    View, views, views! Totally beautiful modern home has a very large balcony which provides an opportunity for endless d ...

    From $280 per night (USD)

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  • Beautiful Lagoon view on canal pool home Summerland
    From $334 per night (USD)

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    Beautiful Lagoon view on canal pool home Summerland

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Home has high vaulted ceiling and 30 feet of sliding glass windows which over looks the canal, lagoon and ocean. On quie ...

    From $334 per night (USD)

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    Details
  • Florida Keys Waterfront House w\/Pool & Spectacular Ocean Views\/Minimum 28 Nights
    From $430 per night (USD)

    VRBO

    Florida Keys Waterfront House w\/Pool & Spectacular Ocean Views\/Minimum 28 Nights

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Beautiful new home on the oceanside of Summerland Key on a protected deep water canal one lot in from the ocean. 45' do ...

    From $430 per night (USD)

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    Details
  • WEEKLY Oceanfront  Home-Pool, Dock-Available Weekly or Monthly.
    From $886 per night (USD)

    VRBO

    WEEKLY Oceanfront Home-Pool, Dock-Available Weekly or Monthly.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,000 square foot custom built home set ...

    From $886 per night (USD)

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    Details
  • THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
    From $199 per night (USD)

    Expedia

    THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The Green Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...

    From $199 per night (USD)

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    Details
  • Mad Mahi - Deep Water Canal
    From $358 per night (USD)

    VRBO

    Mad Mahi - Deep Water Canal

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atl ...

    From $358 per night (USD)

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    Details
  • Ocean View Splendor on Summerland Key
    From $280 per night (USD)

    Expedia

    Ocean View Splendor on Summerland Key

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy the beautiful waterfront elevated home in the Florida Keys overlooking the Atlantic Ocean. Relax in the screened ...

    From $280 per night (USD)

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  • ~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!
    From $900 per night (USD)

    VRBO

    ~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    14

    Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings t ...

    From $900 per night (USD)

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    Details
  • Relaxing 2\/2 Get Away in the Lower Keys! by RedAwning
    From $354 per night (USD)

    Expedia

    Relaxing 2\/2 Get Away in the Lower Keys! by RedAwning

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spacious Canal Front Home with Fast WiFi, Central AC, & Private Hot Tub Chill at a spacious and recently renovated hom ...

    From $354 per night (USD)

    Expedia

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  • Florida Keys Paradise!
    From $303 per night (USD)

    VRBO

    Florida Keys Paradise!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Looking for the ultimate vacation experience? Our vacation home has everything you need to relax and have fun. We are lo ...

    From $303 per night (USD)

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    Details
  • Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
    From $250 per night (USD)

    VRBO

    Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    5

    Newly renovated 2 bedroom, 2.5 bath canal front home with pool in quite, safe neighborhood 25 miles from Key West. House ...

    From $250 per night (USD)

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    Details
  • OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS
    From $299 per night (USD)

    VRBO

    OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Ocean Breeze is the largest of our 5 cottages at 1500 square feet. It's perfect for your family vacation, sleeping 7 pe ...

    From $299 per night (USD)

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    Details
  • SEA SHELL COTTAGE UNIT #2
    From $150 per night (USD)

    Expedia

    SEA SHELL COTTAGE UNIT #2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink and microwave oven. Enjoy the communal outdoor ...

    From $150 per night (USD)

    Expedia

    Details
  • WINTER 2024 DISCOUNT! Large 5 Bedroom Canal Home in Summerland Key, FL w\/ Pool
    From $305 per night (USD)

    VRBO

    WINTER 2024 DISCOUNT! Large 5 Bedroom Canal Home in Summerland Key, FL w\/ Pool

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    11

    Welcome to Palm Mansion! This large family home with 5 bedrooms and 3 full baths is located on a wide, deep canal suited ...

    From $305 per night (USD)

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    Details
  • Super Nice 3 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool!
    From $250 per night (USD)

    Expedia

    Super Nice 3 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Summerland Key House! This amazing 2 bedroom home on Summerland Key is a perfect Keys vacation home! It has e ...

    From $250 per night (USD)

    Expedia

    Details
  • Boat Dock \/ Private Airstrip
    From $258 per night (USD)

    VRBO

    Boat Dock \/ Private Airstrip

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to your Canal Front Oasis on Summerland Key! Dock your boat along the sea wall, offering convenient access to wo ...

    From $258 per night (USD)

    VRBO

    Details
  • Waterfront home with boat\/canal access, screened lanai, & renovated interior
    From $246 per night (USD)

    Expedia

    Waterfront home with boat\/canal access, screened lanai, & renovated interior

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Endless Summerland Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...

    From $246 per night (USD)

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    Details
  • Come relax at Sandy Bottom Beach Cottage!!!!!
    From $450 per night (USD)

    VRBO

    Come relax at Sandy Bottom Beach Cottage!!!!!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Beautiful Summerland Key!! Two houses from the Atlantic Ocean. Enjoy boating, kayaking, swimming in the 28' x 9' swim s ...

    From $450 per night (USD)

    VRBO

    Details
  • Waterfront villa with pool, outdoor areas, home gym, & fillet station
    From $2502 per night (USD)

    Expedia

    Waterfront villa with pool, outdoor areas, home gym, & fillet station

    Bedrooms:
    8
    Bathrooms:
    6
    Sleeps:
    14

    Tarpon Ranch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...

    From $2502 per night (USD)

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  • PEACEFUL PARADISE DEEP WATER CANAL 5 MINUTES TO OCEAN Fishing and Lobster season
    From $395 per night (USD)

    VRBO

    PEACEFUL PARADISE DEEP WATER CANAL 5 MINUTES TO OCEAN Fishing and Lobster season

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Location Location Location! Welcome to our very special community Summerland Key. Summerland is one of the best fishi ...

    From $395 per night (USD)

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  • Open Water ~ Pool Home in Summerland Key
    From $625 per night (USD)

    VRBO

    Open Water ~ Pool Home in Summerland Key

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Prime Oceanfront Tropical Gem & The Ultimate in Luxury Waterfront Living! Florida Keys luxury deep water oceanfront pool ...

    From $625 per night (USD)

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  • Newly Renovated Ocean Estate- Relax and enjoy this magnifecent
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    Newly Renovated Ocean Estate- Relax and enjoy this magnifecent

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Magnificent Ocean Front Estate! Enjoy breathtaking views of the ocean from the large screened in porch. Prepare freshly ...

    Click For Pricing

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  • Reel Caribbean Getaway: Amazing pool, boating
    From $367 per night (USD)

    Expedia

    Reel Caribbean Getaway: Amazing pool, boating

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Fantastic deep-water boating from this spacious, gated, 4 bedroom / 2.5 bath home on Summerland Key's Caribbean Drive Ea ...

    From $367 per night (USD)

    Expedia

    Details
  • Key house on canal 5-minutes to ocean with 75’ of dockage
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    Key house on canal 5-minutes to ocean with 75’ of dockage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    This rustic home offers open beamed ceilings and peek-a-boo views of the ocean from the top living area. Complete with 7 ...

    Click For Pricing

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  • Beautiful Oceanfront Villa with Pool and near Key West, Florida
    From $540 per night (USD)

    VRBO

    Beautiful Oceanfront Villa with Pool and near Key West, Florida

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Make some memories at this unique and family-friendly place. Beautiful, custom designed concrete waterfront pool home wi ...

    From $540 per night (USD)

    VRBO

    Details
  • Luxury Retreat in Summerland Key - Book Today!
    From $1000 per night (USD)

    VRBO

    Luxury Retreat in Summerland Key - Book Today!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Stay in this one-of-a-kind home right in the Channal of Summerland Key. Only 25 min from KeyWest in one of the most soug ...

    From $1000 per night (USD)

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    Details
  • Peaceful ocean front cottage.
    From $250 per night (USD)

    Expedia

    Peaceful ocean front cottage.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breath taking sun ...

    From $250 per night (USD)

    Expedia

    Details
  • Recently Renovated Home With Deepwater Canal
    From $152 per night (USD)

    VRBO

    Recently Renovated Home With Deepwater Canal

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Amazing canal front 3 bed conch style house located in prestigious community of Summerland Key Cove. It is the first can ...

    From $152 per night (USD)

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    Details
  • THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
    From $189 per night (USD)

    Expedia

    THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    PINK COTTAGE UNIT #3 - Sleeps 4 ACCOMODATIONS: UNIT #3 comes with TV, AC, WIFI & Full Kitchen. full kitchen. Enjoy th ...

    From $189 per night (USD)

    Expedia

    Details
  • REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool & Deep Water Access
    From $505 per night (USD)

    VRBO

    REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool & Deep Water Access

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Impeccably designed and maintained canal front home in Summerland Cove with a Pool! This fully fenced and gated para ...

    From $505 per night (USD)

    VRBO

    Details
  • The Love Shack: Charming retreat
    From $139 per night (USD)

    Expedia

    The Love Shack: Charming retreat

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy the beach cottage vibes at this cozy 2 bed/1 bath retreat on the oceanside on Summerland Key. Although not on the ...

    From $139 per night (USD)

    Expedia

    Details
  • Paradise Views: Oceanfront\/Boating
    From $650 per night (USD)

    VRBO

    Paradise Views: Oceanfront\/Boating

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy one of Florida's most tranquil oceanfront settings. A romantic interlude and tropical adventure where absolutely e ...

    From $650 per night (USD)

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  • Summerland Key Oceanfront
    From $300 per night (USD)

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    Summerland Key Oceanfront

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Please check out the new updated photos of all the repairs and updates. The house now has new impact windows and doors, ...

    From $300 per night (USD)

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  • Summerland Key House Open Air Living
    From $273 per night (USD)

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    Summerland Key House Open Air Living

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summerland Key House is all about open air living. Cypress plank cathedral ceilings extend through the bedrooms, bathro ...

    From $273 per night (USD)

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  • Windswept Beach
    From $465 per night (USD)

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    Windswept Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to our newly renovated 3 bedroom, 3 bathroom home with stunning open water views! This modern home is perfect fo ...

    From $465 per night (USD)

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  • 3 Bedroom 3 Bath Pool Home with Gorgeous Atlantic Views
    From $500 per night (USD)

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    3 Bedroom 3 Bath Pool Home with Gorgeous Atlantic Views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to the Prestigious neighborhood of Summerland Key Isles!! This gorgeous 3 bedroom 3 bath property has one of the ...

    From $500 per night (USD)

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  • Beautiful 3 bed 2 bath deep water canal front home
    From $215 per night (USD)

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    Beautiful 3 bed 2 bath deep water canal front home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful 3 bedroom 2 bath canal front home on Summerland Key. This home features deep water dockage, great access to th ...

    From $215 per night (USD)

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  • Deep water Boating ~ Bay Views ~ 3 bed 2 bath + outside shower
    From $190 per night (USD)

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    Deep water Boating ~ Bay Views ~ 3 bed 2 bath + outside shower

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Thank you for checking out the Key Lime Cottage! This deceivingly spacious 3 bedroom 2 bath home is tastefully furnish ...

    From $190 per night (USD)

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  • FLAMINGO COTTAGE UNIT #1
    From $175 per night (USD)

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    FLAMINGO COTTAGE UNIT #1

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The Flamingo Cottage comes with TV, AC & WIFI. UNIT #1 has full kitchen, and it's own private space. Enjoy the communal ...

    From $175 per night (USD)

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  • Summerland Cottage-Relax At Our Little Piece of Paradise!
    From $233 per night (USD)

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    Summerland Cottage-Relax At Our Little Piece of Paradise!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    ** Phone Meeting Required before booking approval!! Host Missy Proctor (561) 667-0160 *** Don't forget to check the VR ...

    From $233 per night (USD)

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  • Summerland Keys Upgraded Waterfront Home
    From $250 per night (USD)

    Expedia

    Summerland Keys Upgraded Waterfront Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax with the whole family at this peaceful oasis on the water with plenty of room for your boat and trailer! With 50 f ...

    From $250 per night (USD)

    Expedia

    Details