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

Beautiful Lagoon view on canal pool home Summerland

Beautiful Lagoon view on canal pool home Summerland

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Summerland Key Florida Private vacation home From $335 per night (USD)

A slice of paradise

A slice of paradise

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Cudjoe Key Florida Cottage From $231 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)

Open Water ~ Pool Home in Summerland Key

Open Water ~ Pool Home in Summerland Key

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Summerland Key Florida Private vacation home From $625 per night (USD)

BIG BLUE waits for you in the sunny Keys

BIG BLUE waits for you in the sunny Keys

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Cudjoe Key Florida Private vacation home From $337 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

Sirena Key Cottage in Venture Out

Sirena Key Cottage in Venture Out

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Cudjoe Key Florida Condo From $270 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)

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

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

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Summerland Key Florida Private vacation home From $420 per night (USD)

Waterfront house conveniently located.

Waterfront house conveniently located.

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Summerland Key Florida Private vacation home From $275 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 $250 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 $170 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)

Waterfront Relaxation and Barefoot Sunsets

Waterfront Relaxation and Barefoot Sunsets

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Cudjoe Key Florida Private vacation home From $205 per night (USD)

Springs Venture Out Dolphin House (#386) with beautiful open water views

Springs Venture Out Dolphin House (#386) with beautiful open water views

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Cudjoe Key Florida Mobile home From $268 per night (USD)

Ocean view home -Private launch & breath taking sunset views-min 28 day rentals

Ocean view home -Private launch & breath taking sunset views-min 28 day rentals

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Cudjoe Key Florida Cottage From $210 per night (USD)

Views Views! Direct Oceanfront, Beautiful Inside!

Views Views! Direct Oceanfront, Beautiful Inside!

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Summerland Key Florida Private vacation home From $301 per night (USD)

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

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

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 $999 per night (USD)

EMPTY RV LOT - Sea Esta in Cudjoe Key!

EMPTY RV LOT - Sea Esta in Cudjoe Key!

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Cudjoe Key Florida Caravan Park/Campsite From $183 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

The edge of the river of Poseidon

The edge of the river of Poseidon

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Cudjoe Key Florida Private vacation home From $400 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)

WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification

WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification

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Cudjoe Key Florida Private vacation home From $215 per night (USD)

water at your back door

water at your back door

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Cudjoe Key Florida Cottage From $327 per night (USD)

$Enjoy Caribbean weather. Last minute opening beginning 4\/6\/24! Enjoy the Keys!$

Enjoy Caribbean weather. Last minute opening beginning 4\/6\/24! Enjoy the Keys!

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Cudjoe Key Florida Private vacation home From $200 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)

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 $275 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)

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 $612 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)

Fishermen’s Paradise 🎣

Fishermen’s Paradise 🎣

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Cudjoe Key Florida Cottage From $245 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 $334 per night (USD)

Tropical Getaway in Paradise.

Tropical Getaway in Paradise.

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Cudjoe Key Florida Private vacation home From $281 per night (USD)

Walk to the Pool - Venture Out Unit 333

Walk to the Pool - Venture Out Unit 333

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Summerland Key Florida Cottage Click For Pricing

House of the Rising Sun - VO479

House of the Rising Sun - VO479

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Cudjoe Key Florida Private vacation home Click For Pricing

Newly Renovated Ocean Estate- Relax and enjoy this magnifecent

Newly Renovated Ocean Estate- Relax and enjoy this magnifecent

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Summerland Key Florida Private vacation home From $714 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

Ocean Front - Private 56' Dock

Ocean Front - Private 56' Dock

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Cudjoe Key Florida Private vacation home Click For Pricing

Relaxing Home in gated community

Relaxing Home in gated community

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

Forever Summer

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

Oceanfront Sunsets in the Florida Keys

Oceanfront Sunsets in the Florida Keys

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Summerland Key Florida Private vacation home From $375 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 $215 per night (USD)

Catch n' Relax in the Keys!

Catch n' Relax in the Keys!

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

Tropical Island Getaway! - Venture Out #653

Tropical Island Getaway! - Venture Out #653

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Cudjoe Key Florida Cottage Click For Pricing

Cozy and modern island living, Cudjoe Key

Cozy and modern island living, Cudjoe Key

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

3 night minimum! Spectacular Ocean Views!

3 night minimum! Spectacular Ocean Views!

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Cudjoe Key Florida Private vacation home From $304 per night (USD)

Ocean Front Modern Home

Ocean Front Modern Home

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Summerland Key Florida Private vacation home From $435 per night (USD)

Sea Breeze Cottage - Venture Out Unit 066

Sea Breeze Cottage - Venture Out Unit 066

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

Mile Marker Mahi - Venture Out #465

Mile Marker Mahi - Venture Out #465

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Cudjoe Key Florida Cottage From $310 per night (USD)

Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 3 Kayaks, WiFi, 2 TV'

Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 3 Kayaks, WiFi, 2 TV'

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

35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

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CUDJOE KEY Florida Mobile home From $285 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 $161 per night (USD)

Reel Caribbean Getaway | 4 Bed, 2.5 Bath

Reel Caribbean Getaway | 4 Bed, 2.5 Bath

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Summerland Key Florida Private vacation home From $367 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)

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)

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

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)

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

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)

Cozy, Perfect Conch Cottage!

Cozy, Perfect Conch Cottage!

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Cudjoe Key Florida Private vacation home From $173 per night (USD)

Manatee Hideaway

Manatee Hideaway

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Cudjoe Key Florida Private vacation home From $325 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 $225 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)

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)

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

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)

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)

One bedroom One bathroom sleeps 4

One bedroom One bathroom sleeps 4

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Cudjoe Key Florida Mobile home Click For Pricing

Waterfront beach house with boat ramp

Waterfront beach house with boat ramp

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Summerland Key Florida Private vacation home From $157 per night (USD)

NAUTILUS...ocean front cottage retreat ~

NAUTILUS...ocean front cottage retreat ~

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Cudjoe Key Florida Cottage From $647 per night (USD)

Oceanside, heated pool, near Key West, space for 20-25 ft boat. Book fall 2024!

Oceanside, heated pool, near Key West, space for 20-25 ft boat. Book fall 2024!

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Cudjoe Key Florida Private vacation home From $203 per night (USD)

LATITUDE ADJUSTMENT

LATITUDE ADJUSTMENT

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Cudjoe Key Florida Private vacation home From $300 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)

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)

Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!

Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!

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Summerland Key Florida Private vacation home From $738 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 $262 per night (USD)

COZY CLEAN on CANAL - Venture Out Unit 342

COZY CLEAN on CANAL - Venture Out Unit 342

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Cudjoe Key Florida Mobile home From $343 per night (USD)

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

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

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Summerland Key Florida Private vacation home Click For Pricing

Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.

Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.

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Cudjoe Key Florida Cottage From $267 per night (USD)

Open Water Views - Venture Out Unit 373

Open Water Views - Venture Out Unit 373

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Cudjoe Key Florida Private vacation home From $375 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 $406 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 $459 per night (USD)

ISLAND PARADISE

ISLAND PARADISE

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Cudjoe Key Florida Hotel resort From $232 per night (USD)

Amazing Open Water Views - Venture Out Unit #374

Amazing Open Water Views - Venture Out Unit #374

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Cudjoe Key Florida Private vacation home From $375 per night (USD)

OCEANFront Gem! True Southern Exposure - Venture Out Unit 93

OCEANFront Gem! True Southern Exposure - Venture Out Unit 93

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Cudjoe Key Florida Private vacation home From $746 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)

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

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

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Cudjoe Key Florida Private vacation home From $243 per night (USD)

Beautiful Ocean Views 35' Dockage - Venture Out unit 469

Beautiful Ocean Views 35' Dockage - Venture Out unit 469

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

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