Family-Friendly Vacation Rentals in Florida Keys Beaches, FL: Compare 10+ Sites & Save

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77 Best Family Vacation Rentals in Florida Keys Beaches (Starting from $210)

Bungalows Sugarloaf Beach Key West - Hammock House
Bungalows Sugarloaf Beach Key West - Hammock House
House
Sugarloaf Shores, FL, USA
0.9k from Florida Keys Beaches center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1695
Average price / night
Check Availability
 Canal Front 3-bedroom house in Sugarloaf Key
Canal Front 3-bedroom house in Sugarloaf Key
House
Summerland Key, FL, 33042, United States
2.9k from Florida Keys Beaches center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$343
Average price / night
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Bungalows Beach Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$1395
Average price / night
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Swimming Pool / Boat Dock / Close to Key West
Swimming Pool / Boat Dock / Close to Key West
House
Sugarloaf, FL, 33042, United States
3.0k from Florida Keys Beaches center

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

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
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Palms Resort Main House - Key West
Palms Resort Main House - Key West
House
Sugarloaf Shores, FL, USA
0.9k from Florida Keys Beaches center

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

1 Bedroom12 Guests
New to Booking
$1248
Average price / night
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Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe
House
SugarLoaf, FL, 33042, United States
4.0k from Florida Keys Beaches center

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

5 Bedrooms12 Guests
9.6

Exceptional

8 reviews

$297
Average price / night
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Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom8 Guests
New to Booking
$1198
Average price / night
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Sugarloaf Key Home With Beach, Dock and Canal!
Sugarloaf Key Home With Beach, Dock and Canal!
House
Sugarloaf Key, FL, 33042, United States
4.1k from Florida Keys Beaches center

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

4 Bedrooms8 Guests
10.0

Exceptional

26 reviews

$712
Average price / night
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Bungalows Beach Key West - Hemingway
Bungalows Beach Key West - Hemingway
House
FL, USA
0.9k from Florida Keys Beaches center

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

2 Bedrooms6 Guests
New to Booking
$1104
Average price / night
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Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!
Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!
House
Key West, FL, 33040, United States
4.6k from Florida Keys Beaches center

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

4 Bedrooms8 Guests
New to Booking
$331
Average price / night
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Coral Queen Palm
Coral Queen Palm
House
Key West, FL, USA
4.6k from Florida Keys Beaches center

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

3 Bedrooms6 Guests
New to Booking
$330
Average price / night
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Key West Beach House with heated pool, tiki, and dock.♿︎
Key West Beach House with heated pool, tiki, and dock.♿︎
House
Key West, FL, 33040, United States
4.7k from Florida Keys Beaches center

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

5 Bedrooms10 Guests
9.6

Exceptional

8 reviews

$646
Average price / night
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Waterfront Key West Oasis with Float Dock!
Waterfront Key West Oasis with Float Dock!
House
Key West, FL, USA
4.7k from Florida Keys Beaches center

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

3 Bedrooms8 Guests
New to Booking
$241
Average price / night
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Home in Blue water Key
Home in Blue water Key
House
Key West, FL, 33040, United States
5.6k from Florida Keys Beaches center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$562
Average price / night
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Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
4.8k from Florida Keys Beaches center

Accommodations, Pools, Parking, Lodges, Cabins, Lodgings, Places to stay, Accessible hotels

13 Bedrooms10 Guests
7.4

Good

552 reviews

$313
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
7.6k from Florida Keys Beaches 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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Villa of the Setting Sun
Villa of the Setting Sun
House
Florida Keys Beaches, Florida, USA
6.4k from Florida Keys Beaches center

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

4 Bedrooms8 Guests
8.0

Good

1 reviews

$2804
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
7.8k from Florida Keys Beaches 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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Pelico Paradise
Pelico Paradise
House
Florida Keys Beaches, Florida, USA
6.5k from Florida Keys Beaches center

Parking, Pet Friendly, Air Conditioner, Internet, Child Friendly

5 Bedrooms10 Guests
9.6

Exceptional

2 reviews

$304
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
7.8k from Florida Keys Beaches 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
6.7k from Florida Keys Beaches 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
7.8k from Florida Keys Beaches 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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Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
House
Upper Sugarloaf Key, FL, 33042, United States
7.9k from Florida Keys Beaches center

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

4 Bedrooms12 Guests
9.2

Superb

7 reviews

$534
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
8.3k from Florida Keys Beaches 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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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
8.4k from Florida Keys Beaches 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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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
8.5k from Florida Keys Beaches 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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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
8.6k from Florida Keys Beaches center

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

1 Bedroom2 Guests
8.6

Fabulous

162 reviews

$210
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 Florida Keys Beaches.

Where to stay in Florida Keys Beaches? Best neighborhoods & areas

Florida Keys Beaches Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 77 verified family-friendly vacation rentals in Florida Keys Beaches. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Florida Keys Beaches vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $210 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Florida Keys Beaches 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 Florida Keys Beaches 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 Florida Keys Beaches often include amenities such as Child Friendly, View, and Balcony/Terrace. 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.