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Houses for Rent and Vacation Rentals in Cudjoe Key, FL
Vacation Rentals
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Florida (FL)
Florida Keys
Cudjoe Key
Cudjoe Key House Rentals
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Bedrooms
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Bathrooms
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Amenities
Internet or Wifi (248)
Washer/Dryer (246)
Air Conditioning (230)
Grill (219)
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Suitability
Kid friendly (265)
Pet friendly (119)
Smoking allowed (31)
Wheelchair access (0)
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Property type
Vacation Rental House (272)
Condominium/Apartment (0)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (164)
Boat Available (41)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Angelic Moon Holistic Day Spa & APOTHECARY
Cudjoe Sales
Walkabout Retreats Gear Rentals
Nothing Better Rentals, LLC
Cudjoe Key Boat Rentals
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272 rentals
in Cudjoe Key.
Canal front, dockage, 2 bedroom, 2 bath
11
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
35
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Blue Vacation Home Free Cancellation See Details
140
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
13
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, Vacation Rental House
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As seen on
Keys Sanctuary In A Gated Community With Dock And Pool On Atlantic Ocean
41
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Relax by Florida Keys Beaches, just a 7-min drive away
163
Rental Home
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2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps, Vacation Rental House
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Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
167
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, Vacation Rental House
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As seen on
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
22
Rental Home
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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As seen on
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
87
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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20 MINUTES TO KEY WEST , BOATERS PARADISE
39
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
25
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Private Oceanfront Cottage with dockage, pool just minutes to Key West!
6
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps, Vacation Rental House
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Cottage with swimming pool and dockage, just minutes to Key West!
29
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps, Vacation Rental House
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Location, location, location briefly describes this small piece of Paradise.
39
Rental Home
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3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Cottage with Pool and Boat Dockage just minutes to Key West!
33
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps, Vacation Rental House
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Fishermen’s Paradise
89
Rental Home
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Waterfront Home
36
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Charming cottages, dockage, pool, just minutes to Key West
93
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak
1
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Comfortable Waterfront Vacation Rental
131
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
44
Rental Home
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3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Island Therapy
22
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Tropical Island Paradise W / Open Water Views!
54
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
22
Rental Home
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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As seen on
"WEEKLY RENTAL" Florida Keys Pool & Waterfront Vacation Rental 108
45
Rental Home
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
16
Rental Home
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
More info
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As seen on
Yellow Vacation Home Free Cancelation See Details
32
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
23
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Cudjoe Cottages, swimming pool, just 20 miles from Key West
117
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, Bikes, Views!
10
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
21
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
White Vacation Home Free Cancellation See Details
185
Rental Home
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
More info
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As seen on
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
18
Rental Home
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
More info
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As seen on
**MERMAID MAGIC * VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
15
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Sun Bake * Sponge Cake, 64' Sea Wall, Great Seating, Fish Gulf or Atlantic
13
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
Oceanside home, dock,kayaks,bikes,pool,fishing,109
34
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
Latitudes - Ocean front with pool
18
Rental Home
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6 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps, Vacation Rental House
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Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
197
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
Oceanside home, dock,kayaks,bikes,pool,fishing,111
144
Rental Home
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3 bedrooms
6 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
Cottage with Pool and Dockage, just minutes to Key West
34
Rental Home
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
51
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Pelican's Roost, Waterfront comfort at Venture Out
5
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps, Vacation Rental House
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35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
120
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
Keys Time #437 - Cudjoe Key, Oceanfront Community
17
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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As seen on
**TIDEWATER VIEWS * VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
27
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Fandango - private pool
12
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps, Vacation Rental House
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Springs Venture Out Dolphin House (#386) with beautiful open water views
79
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Private Cottage with Pool and Dock
31
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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As seen on
Spanish Queen *Venture Out, Cudjoe Key
14
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Enjoy Caribbean weather in the USA. Openings in April 2025!! Book now!
126
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps, Vacation Rental House
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