Beach Home Rentals in Cudjoe Key, FL: Compare 10+ Sites & Save

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  5.  Cudjoe Key

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59 Beach Home Rentals in Cudjoe Key (Starting from $156)

Ocean View with Pool, 4 bedroom Vila Near Key West
Ocean View with Pool, 4 bedroom Vila Near Key West
Villa
Cudjoe Key, FL, USA
1.1k from Cudjoe Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$810
Average price / night
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102 - Newly renovated house Oceanside  and Pool
102 - Newly renovated house Oceanside and Pool
House
Cudjoe Key, FL, 33042, United States
0.8k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$645
Average price / night
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Tranquility in Paradise - Cudjoe
Tranquility in Paradise - Cudjoe
House
Summerland Key, FL, USA
1.5k from Cudjoe Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$156
Average price / night
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101-  Oceanside House with Pool
101- Oceanside House with Pool
House
Cudjoe Key, FL, 33042, United States
0.8k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$551
Average price / night
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Newly built home in Cudjoe Key
Newly built home in Cudjoe Key
House
Cudjoe Key, FL, USA
1.9k from Cudjoe Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms7 Guests
New to Booking
$583
Average price / night
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106- Newly Renovated House with Oceanview and Pool
106- Newly Renovated House with Oceanview and Pool
House
Cudjoe Key, FL, 33042, United States
0.9k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$583
Average price / night
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Blue Palms w/boat dock and saltwater pool.
Blue Palms w/boat dock and saltwater pool.
House
Cudjoe Key, FL, 33042, United States
0.9k from Cudjoe Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
9.8

Exceptional

158 reviews

$579
Average price / night
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Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
House
Summerland, FL, 33042, United States
0.9k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
9.6

Exceptional

80 reviews

$806
Average price / night
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Latitudes - Ocean front with salt water pool.
Latitudes - Ocean front with salt water pool.
House
Cudjoe Key, FL, 33042, United States
0.9k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

6 Bedrooms12 Guests
9.8

Exceptional

45 reviews

$801
Average price / night
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The Grand Tiki Estate - Private Dock, Pool & Endless Ocean Views
The Grand Tiki Estate - Private Dock, Pool & Endless Ocean Views
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$784
Average price / night
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Oceanside home, dock,kayaks,bikes,pool,fishing,109
Oceanside home, dock,kayaks,bikes,pool,fishing,109
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

1 Bedroom6 Guests
10.0

Exceptional

178 reviews

$545
Average price / night
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Oceanside home, dock,kayaks,bikes,pool,fishing,111
Oceanside home, dock,kayaks,bikes,pool,fishing,111
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

158 reviews

$605
Average price / night
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Oceanside home, dock,kayaks,bikes,pool,fishing,107
Oceanside home, dock,kayaks,bikes,pool,fishing,107
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Heater, Internet, Kitchen

2 Bedrooms6 Guests
9.8

Exceptional

195 reviews

$520
Average price / night
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\"WEEKLY RENTAL\" Florida Keys Pool & Waterfront Vacation Rental 108
\"WEEKLY RENTAL\" Florida Keys Pool & Waterfront Vacation Rental 108
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
9.8

Exceptional

136 reviews

$397
Average price / night
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Luxurious Oceanfront Home on Beach, Pool, Dock, Kayaks, Bikes, Amazing Views!
Luxurious Oceanfront Home on Beach, Pool, Dock, Kayaks, Bikes, Amazing Views!
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
10.0

Exceptional

207 reviews

$568
Average price / night
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Family Retreat Ocean front pool
Family Retreat Ocean front pool
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, No Smoking

5 Bedrooms14 Guests
9.4

Superb

91 reviews

$846
Average price / night
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Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

233 reviews

$481
Average price / night
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Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
8.6

Fabulous

96 reviews

$773
Average price / night
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cottage
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.0

Fabulous

57 reviews

$286
Average price / night
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Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with Pool
Villa
125 Colson Dr, Summerland Key, FL, 33042, United States
1.1k from Cudjoe Key center

Barbecue, Business Services, Free Parking, Hot Tub, Internet, Kids Pool, Laundry, Living Area, No Smoking

10.0

Exceptional

2 reviews

$1096
Average price / night
Check Availability
Beachfront • Heated Pool • Hot Tub • Oceanview
Beachfront • Heated Pool • Hot Tub • Oceanview
Villa
Cudjoe Key, FL, 33042, United States
1.1k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Living Area

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$947
Average price / night
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Upscale Canal-Front Escape w/ Private Pool, Dock & Water Views
Upscale Canal-Front Escape w/ Private Pool, Dock & Water Views
House
Cudjoe Key, FL, 33042, United States
1.3k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms6 Guests
New to Booking
$341
Average price / night
Check Availability
Fisherman's Paradise
Fisherman's Paradise
House
Cudjoe Key, FL, 33042, United States
1.3k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$884
Average price / night
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Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool
Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool
House
Cudjoe Key, FL, 33042, United States
1.4k from Cudjoe Key center

AC, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$393
Average price / night
Check Availability
Villa Jekjak
Villa Jekjak
House
Summerland Key, FL, 33042, United States
1.4k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$407
Average price / night
Check Availability
Oceanside, pet friendly, smart home with plenty of paddle equipment
Oceanside, pet friendly, smart home with plenty of paddle equipment
House
Cudjoe Key, FL, 33042, United States
1.5k from Cudjoe Key center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
9.6

Exceptional

29 reviews

$214
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Beach Rentals in Cudjoe Key.

Stay Near Cudjoe Key's Top Attractions

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Cudjoe Key Beach Rentals on the Map

Frequently Asked Questions

You can explore 59 verified beach rentals in Cudjoe Key. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Cudjoe Key vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $156 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Cudjoe Key offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Cudjoe Key welcome pets. Currently, 30 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Cudjoe Key often include amenities designed for coastal living, such as Ocean View, View, and Balcony/Terrace. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.