Family-Friendly Vacation Rentals in Cudjoe Key, FL: Compare 10+ Sites & Save

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  5.  Cudjoe Key

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92 Best Family Vacation Rentals in Cudjoe Key (Starting from $156)

Unit 101
Unit 101
House
Cudjoe Key, FL, USA
1.0k from Cudjoe Key center

Security/Safety, Pool, Hot Tub, Wellness Facilities, Air Conditioner, View, Balcony/Terrace

5 Bedrooms6 Guests
New to Booking
$405
Average price / night
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Cottage with Pool  and Boat Dockage just minutes to Key West!
Cottage with Pool and Boat Dockage just minutes to Key West!
Cottage
Cudjoe Key, FL, 33042, United States
0.9k from Cudjoe Key center

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

1 Bedroom2 Guests
8.6

Fabulous

162 reviews

$210
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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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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Yellow Home - Receive 400 dollars \ntowards a BOAT RENTAL!
Yellow Home - Receive 400 dollars \ntowards a BOAT RENTAL!
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

149 reviews

$492
Average price / night
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Luxury OceanView Friendly Villa Near Key West
Luxury OceanView Friendly Villa Near Key West
Villa
Cudjoe Key, Florida, USA
1.2k from Cudjoe Key center

Pool, Parking, Laundry, Hot Tub, Balcony/Terrace, Pet Friendly, Kitchen

4 Bedrooms10 Guests
1.0

Review score

1 reviews

$804
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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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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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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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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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
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Key Lime Time
Key Lime Time
House
Cudjoe Key, FL, USA
2.1k from Cudjoe Key center

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

4 Bedrooms12 Guests
New to Booking
$363
Average price / night
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White Home - Receive 400 dollars \ntowards a BOAT RENTAL!
White Home - Receive 400 dollars \ntowards a BOAT RENTAL!
House
Cudjoe Key, FL, 33042, United States
1.1k from Cudjoe Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

207 reviews

$520
Average price / night
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Red Grouper Getaway
Red Grouper Getaway
House
Cudjoe Key, FL, USA
2.3k from Cudjoe Key center

Laundry, Parking, Internet, Balcony/Terrace, Air Conditioner, Pet Friendly, Child Friendly

3 Bedrooms8 Guests
New to Booking
$311
Average price / night
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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
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Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages
House
Summerland Key, FL, USA
2.9k from Cudjoe Key center

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

20 Bedrooms12 Guests
9.0

Fabulous

314 reviews

$458
Average price / night
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Private Secluded Ocean View & Pool Near Key West
Private Secluded Ocean View & Pool Near Key West
House
Summerland Key, FL, 33042, United States
1.6k from Cudjoe Key center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
8.0

Good

103 reviews

$750
Average price / night
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Pelican's Roost, Waterfront comfort at Venture Out
Pelican's Roost, Waterfront comfort at Venture Out
House
Cudjoe Key, FL, USA
3.2k from Cudjoe Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms5 Guests
9.2

Superb

15 reviews

$303
Average price / night
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Magnificent Ocean views, privacy abounds on this well appointed mini estate.
Magnificent Ocean views, privacy abounds on this well appointed mini estate.
House
Cudjoe Key, FL, 33042, United States
1.7k from Cudjoe Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$532
Average price / night
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Turtle Cove Views by Last Key Realty
Turtle Cove Views by Last Key Realty
House
Cudjoe Key, FL, USA
3.2k from Cudjoe Key center

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

2 Bedrooms6 Guests
7.0

Good

1 reviews

$513
Average price / night
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Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool
Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool
House
Cudjoe Key, FL, 33042, United States
1.9k from Cudjoe Key center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Free Parking, Heater

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$499
Average price / night
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Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
House
Cudjoe Key, FL, 33042, United States
2.3k from Cudjoe Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$401
Average price / night
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NEPTUNES END - 4 Bedrooms / 3 Bathrooms Waterfront Retreat-  Pool & Sunset Views
NEPTUNES END - 4 Bedrooms / 3 Bathrooms Waterfront Retreat- Pool & Sunset Views
House
Cudjoe Key, FL, 33042, United States
2.4k from Cudjoe Key center

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

4 Bedrooms12 Guests
9.2

Superb

9 reviews

$453
Average price / night
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Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
House
Summerland Key, FL, 33042, United States
2.9k from Cudjoe Key center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$773
Average price / night
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Cudjoe Bay Getaway In Paradise
Cudjoe Bay Getaway In Paradise
House
Cudjoe Key, FL, 33042, United States
3.0k from Cudjoe Key center

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

3 Bedrooms6 Guests
9.4

Superb

8 reviews

$234
Average price / night
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Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
House
Cudjoe Key, FL, 33042, United States
3.0k from Cudjoe Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$555
Average price / night
Check Availability
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
House
Cudjoe Key, FL, 33042, United States
3.1k from Cudjoe Key center

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

2 Bedrooms6 Guests
9.8

Exceptional

262 reviews

$285
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 Family Vacation Rentals in Cudjoe Key.

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Cudjoe Key Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 92 verified family-friendly vacation rentals in Cudjoe Key. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Cudjoe Key vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $156 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Cudjoe Key offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Cudjoe Key are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Cudjoe Key often include amenities such as Child Friendly, Balcony/Terrace, and Pool. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.