Summerland Key Vacation Rentals - Summerland Key, Florida Vacation Rental Deals on Lake Rentals, Beach Houses, Condos, Cabins, Villas by VacaGuru.com!

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

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

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Summerland Key Florida Private vacation home From $1099 per night (USD)

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

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

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Summerland Key Florida Private vacation home Click For Pricing

Forever Summer

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Summerland Key Florida Private vacation home From $289 per night (USD)

Summerland Cove Paradise Waterfront Deep Water Canal

Summerland Cove Paradise Waterfront Deep Water Canal

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Summerland Key Florida Private vacation home From $214 per night (USD)

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

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

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Summerland Key Florida Private vacation home From $124 per night (USD)

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

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

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Summerland Key Florida Private vacation home From $410 per night (USD)

$Canalfront house with private pool, WiFi, private washer\/dryer, and central AC$

Canalfront house with private pool, WiFi, private washer\/dryer, and central AC

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Summerland Key Florida Private vacation home From $223 per night (USD)

Summerland Breeze - Three house retreat, perfect for multiple families

Summerland Breeze - Three house retreat, perfect for multiple families

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Summerland Key Florida Private vacation home From $1000 per night (USD)

Tropical Island Sanctuary

Tropical Island Sanctuary

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Summerland Key Florida Private vacation home From $152 per night (USD)

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

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

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Summerland Key Florida Private vacation home From $257 per night (USD)

Location Location! Beautiful views from every angle. Summerland Cove rare point

Location Location! Beautiful views from every angle. Summerland Cove rare point

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Summerland Key Florida Private vacation home Click For Pricing

Beach Bliss, Oceanfront with pool

Beach Bliss, Oceanfront with pool

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Summerland Key Florida Private vacation home From $550 per night (USD)

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

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

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Summerland Key Florida Private vacation home From $250 per night (USD)

Luxurious, Private, Oceanfront, Gated Home

Luxurious, Private, Oceanfront, Gated Home

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Summerland Key Florida Private vacation home From $960 per night (USD)

Summerland Nest - Oceanfront with pool

Summerland Nest - Oceanfront with pool

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Summerland Key Florida Private vacation home From $715 per night (USD)

Mariners Cove - The Kraken House

Mariners Cove - The Kraken House

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Summerland Key Florida Private vacation home From $600 per night (USD)

Canal Front (Deep Water) Tropical Villa

Canal Front (Deep Water) Tropical Villa

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Summerland Key Florida Private vacation home From $220 per night (USD)

Relax at the flying hogfish

Relax at the flying hogfish

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Summerland Key Florida Private vacation home From $175 per night (USD)

$Solstice Seaside Waterfront House w\/Pool & Spectacular Ocean Views\/Min 28 Nights$

Solstice Seaside Waterfront House w\/Pool & Spectacular Ocean Views\/Min 28 Nights

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Summerland Key Florida Private vacation home From $430 per night (USD)

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

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

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Summerland Key Florida Private vacation home Click For Pricing

THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4

THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4

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Summerland Key Florida Cottage From $199 per night (USD)

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

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

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Summerland Key Florida Private vacation home From $354 per night (USD)

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

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

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Summerland Key Florida Private vacation home From $900 per night (USD)

Florida Keys Paradise!

Florida Keys Paradise!

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Summerland Key Florida Private vacation home From $255 per night (USD)

OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS

OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS

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Summerland Key Florida Cottage From $299 per night (USD)

SEA SHELL COTTAGE UNIT #2

SEA SHELL COTTAGE UNIT #2

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Summerland Key Florida Cottage From $150 per night (USD)

Large 5 Bedroom Canal Home in Summerland Key, FL with Pool

Large 5 Bedroom Canal Home in Summerland Key, FL with Pool

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Summerland Key Florida Private vacation home From $305 per night (USD)

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

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

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Summerland Key Florida Private vacation home Click For Pricing

$Boat Dock \/ Private Airstrip$

Boat Dock \/ Private Airstrip

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Summerland Key Florida Private vacation home From $259 per night (USD)

Love Shack | 2 Bed, 1 Bath

Love Shack | 2 Bed, 1 Bath

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Summerland Key Florida Private vacation home From $125 per night (USD)

Recently Renovated Home With Deepwater Canal

Recently Renovated Home With Deepwater Canal

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Summerland Key Florida Private vacation home From $170 per night (USD)

Beautiful Oceanfront Villa with Pool and near Key West, Florida

Beautiful Oceanfront Villa with Pool and near Key West, Florida

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Summerland Key Florida Villa From $540 per night (USD)

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

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

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Summerland Key Florida Cottage From $189 per night (USD)

Summerland Key Oceanfront

Summerland Key Oceanfront

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Summerland Key Florida Private vacation home From $300 per night (USD)

$Views! Waterfront Niles Channel Pool\/dock Industerial Ice Maker$

Views! Waterfront Niles Channel Pool\/dock Industerial Ice Maker

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Summerland Key Florida Private vacation home From $700 per night (USD)

$Paradise Views: Oceanfront\/Boating$

Paradise Views: Oceanfront\/Boating

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Summerland Key Florida Private vacation home From $650 per night (USD)

Summerland Keys Upgraded Waterfront Home

Summerland Keys Upgraded Waterfront Home

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Summerland Key Florida Private vacation home From $270 per night (USD)

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

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

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Summerland Key Florida Private vacation home From $190 per night (USD)

Windswept Beach

Windswept Beach

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Summerland Key Florida Private vacation home From $465 per night (USD)

FLAMINGO COTTAGE UNIT #1

FLAMINGO COTTAGE UNIT #1

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Summerland Key Florida Private vacation home From $184 per night (USD)

Summerland Cottage-Relax At Our Little Piece of Paradise!

Summerland Cottage-Relax At Our Little Piece of Paradise!

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Summerland Key Florida Private vacation home From $233 per night (USD)

Summerland Key House Open Air Living

Summerland Key House Open Air Living

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Summerland Key Florida Private vacation home From $262 per night (USD)

Bimini Breeze in Cudjoe Key

Bimini Breeze in Cudjoe Key

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Cudjoe Key Florida Private vacation home From $275 per night (USD)

$Our Florida Keys \Sea-Cove\! Canal front, Boat dockage, Pool, Private!!$

Our Florida Keys \"Sea-Cove\"! Canal front, Boat dockage, Pool, Private!!

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Summerland Key Florida Private vacation home From $270 per night (USD)

Stunning Oceanfront Keys Home

Stunning Oceanfront Keys Home

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Summerland Key Florida Private vacation home From $295 per night (USD)

Stylish & Modern Summerland Key Private Retreat!

Stylish & Modern Summerland Key Private Retreat!

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Summerland Key Florida Private vacation home From $258 per night (USD)

$Waterfront RV Lot w 35' dock in \Venture Out\$

Waterfront RV Lot w 35' dock in \"Venture Out\"

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Cudjoe Key Florida Caravan Park/Campsite From $110 per night (USD)

Emerald Seas - Florida Keys Ocean Front Paradise!

Emerald Seas - Florida Keys Ocean Front Paradise!

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Cudjoe Key Florida Villa From $400 per night (USD)

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

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Summerland Key Florida Private vacation home From $400 per night (USD)

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

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Cudjoe Key Florida Cottage From $299 per night (USD)

Come stay and play in the Florida Keys!

Come stay and play in the Florida Keys!

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Cudjoe Key Florida Mobile home Click For Pricing

$Canal-front home w\/dock, resort-style amenities, patio, & high-speed WiFi$

Canal-front home w\/dock, resort-style amenities, patio, & high-speed WiFi

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Cudjoe Key Florida Private vacation home From $248 per night (USD)

Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub

Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub

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Cudjoe Key Florida Private vacation home From $225 per night (USD)

**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…

**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…

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Cudjoe Key Florida Private vacation home From $357 per night (USD)

**POSTCARD POINT @ VENTURE OUT** New Waterfront Home + LAST KEY SERVICES…

**POSTCARD POINT @ VENTURE OUT** New Waterfront Home + LAST KEY SERVICES…

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Cudjoe Key Florida Private vacation home From $430 per night (USD)

Canal front home @ Venture Out Resort in the Florida Keys!

Canal front home @ Venture Out Resort in the Florida Keys!

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Cudjoe Key Florida Private vacation home From $366 per night (USD)

Nice home on Atlantic side of Cudjoe Key!

Nice home on Atlantic side of Cudjoe Key!

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Cudjoe Key Florida Private vacation home From $180 per night (USD)

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

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Cudjoe Florida Private vacation home From $275 per night (USD)

$Dog-Friendly, Canal-Front Home w\/Free WiFi, Central AC, Private W\/D, Boat Access$

Dog-Friendly, Canal-Front Home w\/Free WiFi, Central AC, Private W\/D, Boat Access

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Cudjoe Key Florida Private vacation home From $123 per night (USD)

$**TURTLE COVE VIEWS @ VENTURE OUT** 2BR\/2BA Cottage +35’ Private Slip | 80’ Pool$

**TURTLE COVE VIEWS @ VENTURE OUT** 2BR\/2BA Cottage +35’ Private Slip | 80’ Pool

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Cudjoe Key Florida Cottage From $467 per night (USD)

44ft Seawall at Sportsman's Paradise

44ft Seawall at Sportsman's Paradise

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Summerland Key Florida Private vacation home From $636 per night (USD)

WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental

WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental

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Cudjoe Key Florida Private vacation home From $255 per night (USD)

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

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Cudjoe Key Florida Private vacation home From $288 per night (USD)

Sirena Key Cottage in Venture Out

Sirena Key Cottage in Venture Out

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Cudjoe Key Florida Condo From $293 per night (USD)

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage

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Summerland Key Florida Private vacation home From $200 per night (USD)

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

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Cudjoe Key Florida Private vacation home From $225 per night (USD)

Cudjoe Bay Access Vacation House In Paradise

Cudjoe Bay Access Vacation House In Paradise

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Cudjoe Key Florida Private vacation home From $200 per night (USD)

Casa Del Mar in Venture Out Unit 253

Casa Del Mar in Venture Out Unit 253

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Cudjoe Key Florida Mobile home From $273 per night (USD)

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

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

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Summerland Key Florida Private vacation home From $300 per night (USD)

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

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Cudjoe Key Florida Private vacation home From $250 per night (USD)

Blue Chill Vacation!!!

Blue Chill Vacation!!!

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Cudjoe Key Florida Private vacation home Click For Pricing

Seascape Vacation!!!

Seascape Vacation!!!

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Cudjoe Key Florida Private vacation home From $172 per night (USD)

Seas The Day in Cudjoe Key

Seas The Day in Cudjoe Key

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Cudjoe Key Florida Private vacation home From $195 per night (USD)

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!

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Cudjoe Key Florida Cottage From $657 per night (USD)

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!

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Summerland Key Florida Private vacation home From $237 per night (USD)

water at your back door

water at your back door

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Cudjoe Key Florida Cottage From $340 per night (USD)

$Enjoy Caribbean weather. Last minute opening beginning 5\/2\/24! Enjoy the Keys!$

Enjoy Caribbean weather. Last minute opening beginning 5\/2\/24! Enjoy the Keys!

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Cudjoe Key Florida Private vacation home From $200 per night (USD)

Island Therapy

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Cudjoe Key Florida Private vacation home From $220 per night (USD)

Judy's place at Venture Out

Judy's place at Venture Out

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Cudjoe Key Florida Mobile home Click For Pricing

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

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

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Summerland Key Florida Private vacation home From $175 per night (USD)

$Kokomo 3\/2 home on canal quick boating access Cudjoe Harbor$

Kokomo 3\/2 home on canal quick boating access Cudjoe Harbor

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Summerland Key Florida Private vacation home Click For Pricing

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

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Cudjoe Key Florida Private vacation home From $300 per night (USD)

$**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool$

**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool

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Cudjoe Key Florida Cottage From $352 per night (USD)

Tropical Getaway in Paradise.

Tropical Getaway in Paradise.

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Cudjoe Key Florida Private vacation home From $288 per night (USD)

Ocean Front Modern Home

Ocean Front Modern Home

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Summerland Key Florida Private vacation home From $444 per night (USD)

Latitude Adjustment | 3 Bed, 2 Bath

Latitude Adjustment | 3 Bed, 2 Bath

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Summerland Key Florida Private vacation home From $199 per night (USD)

Paradise Found | 3 Bed, 2 Bath

Paradise Found | 3 Bed, 2 Bath

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Cudjoe Key Florida Private vacation home From $170 per night (USD)

Blackbeard`s Hideaway: Cozy canalfront cottage is an angler's dream on Cudjoe Key

Blackbeard`s Hideaway: Cozy canalfront cottage is an angler's dream on Cudjoe Key

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Summerland Key Florida Private vacation home From $165 per night (USD)

Foster`s Folly | 3 Bed, 2 Bath

Foster`s Folly | 3 Bed, 2 Bath

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Summerland Key Florida Private vacation home From $286 per night (USD)

$Beautiful, 2100 sq ft 3\/2 w\/ocean views & easy ocean & gulf access.$

Beautiful, 2100 sq ft 3\/2 w\/ocean views & easy ocean & gulf access.

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Cudjoe Key Florida Private vacation home From $280 per night (USD)

$Oceanside Paradise: Kayaks, Free WiFi, A\/C, Grill, Elevated Deck, 24hr Security$

Oceanside Paradise: Kayaks, Free WiFi, A\/C, Grill, Elevated Deck, 24hr Security

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Cudjoe Key Florida Private vacation home From $140 per night (USD)

Cozy, Perfect Conch Cottage!

Cozy, Perfect Conch Cottage!

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Cudjoe Key Florida Private vacation home From $171 per night (USD)

Captains Quarters - Cudjoe Key - Pool- Up to 45' Boat

Captains Quarters - Cudjoe Key - Pool- Up to 45' Boat

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Cudjoe Key Florida Private vacation home From $403 per night (USD)

Waterfront Home

Waterfront Home

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Cudjoe Key Florida Cottage From $235 per night (USD)

Calypso Cottage Awaits!

Calypso Cottage Awaits!

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Cudjoe Key Florida Cottage Click For Pricing

Oceanfront Home With Large Private Deck with boat dockage

Oceanfront Home With Large Private Deck with boat dockage

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Summerland Key Florida Private vacation home From $352 per night (USD)

Canal Front Home, Heated Pool, Fisherman's Dream

Canal Front Home, Heated Pool, Fisherman's Dream

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Cudjoe Key Florida Private vacation home From $216 per night (USD)

Manatee Hideaway

Manatee Hideaway

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Cudjoe Key Florida Private vacation home From $325 per night (USD)

$RELAX IN HEAVENLY PARADISE - CUDJOE KEY GETAWAY\n3 MINUTES TO OPEN WATERS$

RELAX IN HEAVENLY PARADISE - CUDJOE KEY GETAWAY\n3 MINUTES TO OPEN WATERS

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Cudjoe Key Florida Private vacation home From $195 per night (USD)

Location, location, location briefly describes this small piece of Paradise.

Location, location, location briefly describes this small piece of Paradise.

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Cudjoe Key Florida Cottage From $288 per night (USD)

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