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Cudjoe Key, FL Holiday Rentals
Holiday Rentals
USA
Florida (FL)
Florida Keys
Cudjoe Key, FL Holiday Rentals
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Cudjoe Key
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Internet or Wifi (252)
Washer/Dryer (250)
Air Conditioning (232)
Grill (220)
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Suitability
Kid friendly (270)
Pet friendly (122)
Smoking allowed (33)
Wheelchair access (0)
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Property type
Holiday Rental House (272)
Condominium/Apartment (5)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (165)
Boat Available (41)
Private Chef (0)
Private Beach (0)
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Distance from
5 km
Angelic Moon Holistic Day Spa & APOTHECARY
Cudjoe Sales
Walkabout Retreats Gear Rentals
Nothing Better Rentals, LLC
Cudjoe Key Boat Rentals
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277 rentals
in Cudjoe Key.
Canal front, dockage, 2 bedroom, 2 bath
11
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Sleeps
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
35
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Blue Vacation Home Free Cancellation See Details
140
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
13
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Keys Sanctuary In A Gated Community With Dock And Pool On Atlantic Ocean
41
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Relax by Florida Keys Beaches, just a 7-min drive away
163
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
167
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Sleeps
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
22
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Just 20 miles from Key West! Oceanfront, dockage, swimming pool
87
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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20 MINUTES TO KEY WEST , BOATERS PARADISE
39
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
25
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Private Oceanfront Cottage with dockage, pool just minutes to Key West!
6
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Cottage with swimming pool and dockage, just minutes to Key West!
29
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Sleeps
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Location, location, location briefly describes this small piece of Paradise.
39
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Cottage with Pool and Boat Dockage just minutes to Key West!
33
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Fishermen’s Paradise
89
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Waterfront Home
36
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Charming cottages, dockage, pool, just minutes to Key West
93
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak
1
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Comfortable Waterfront Vacation Rental
131
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
44
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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Island Therapy
22
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Tropical Island Paradise W / Open Water Views!
54
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
22
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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"WEEKLY RENTAL" Florida Keys Pool & Waterfront Vacation Rental 108
45
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
16
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
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As seen on
Yellow Vacation Home Free Cancelation See Details
32
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
23
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Cudjoe Cottages, swimming pool, just 20 miles from Key West
117
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
21
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, Bikes, Views!
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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White Vacation Home Free Cancellation See Details
185
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
18
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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**MERMAID MAGIC * VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
15
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Sun Bake * Sponge Cake, 64' Sea Wall, Great Seating, Fish Gulf or Atlantic
13
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Oceanside home, dock,kayaks,bikes,pool,fishing,109
34
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Latitudes - Ocean front with pool
18
Holiday Rental House
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6 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
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Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
197
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Oceanside home, dock,kayaks,bikes,pool,fishing,111
144
Holiday Rental House
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3 bedrooms
6 bathrooms
Sleeps 6
Match:
Sleeps
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Cottage with Pool and Dockage, just minutes to Key West
34
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
51
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Pelican's Roost, Waterfront comfort at Venture Out
5
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
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35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
120
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Keys Time #437 - Cudjoe Key, Oceanfront Community
17
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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**TIDEWATER VIEWS * VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
27
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Fandango - private pool
12
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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Springs Venture Out Dolphin House (#386) with beautiful open water views
79
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Private Cottage with Pool and Dock
31
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Spanish Queen *Venture Out, Cudjoe Key
14
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Enjoy Caribbean weather in the USA. Openings in April 2025!! Book now!
126
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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1
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Showing results 1-50 of 277
Frequently Asked Questions about Cudjoe Key
Do any holiday rentals in Cudjoe Key have a pool?
Yes, here are some popular holiday rentals in Cudjoe Key that have a pool:
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Canal front, dockage, 2 bedroom, 2 bath
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
See all holiday rentals with a pool in Cudjoe Key on Tripadvisor
Do any holiday rentals in Cudjoe Key have internet access?
Yes, here are some popular holiday rentals in Cudjoe Key that have internet access:
Canal front, dockage, 2 bedroom, 2 bath
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Vacation Home Free Cancellation See Details
See all holiday rentals in Cudjoe Key on Tripadvisor
What are the best pet friendly rentals in Cudjoe Key?
The best pet friendly rentals in Cudjoe Key are:
Canal front, dockage, 2 bedroom, 2 bath
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Relax by Florida Keys Beaches, just a 7-min drive away
See all pet friendly holiday rentals in Cudjoe Key on Tripadvisor
What are some great rentals in Cudjoe Key that are kid friendly?
Some of the most popular kid friendly rentals in Cudjoe Key are:
Canal front, dockage, 2 bedroom, 2 bath
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Vacation Home Free Cancellation See Details
See all kid friendly holiday rentals in Cudjoe Key on Tripadvisor
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