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

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61 Best Family Vacation Rentals in Shark Key (Starting from $197)

Jewel on Jade
Jewel on Jade
House
Key West, FL, USA
0.9k from Shark Key center

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

2 Bedrooms6 Guests
New to Booking
$197
Average price / night
Check Availability
Fisherman's Paradise on the Water
Fisherman's Paradise on the Water
House
Key West, FL, 33040, United States
1.1k from Shark Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$369
Average price / night
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Sapphire Sabbatical
Sapphire Sabbatical
House
Key West, FL, USA
1.0k from Shark Key center

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

3 Bedrooms6 Guests
New to Booking
$253
Average price / night
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Private Paradise, Waterfront Home - 15 minutes from Key West
Private Paradise, Waterfront Home - 15 minutes from Key West
House
Key West, FL, 33040, United States
2.8k from Shark Key center

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

4 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$499
Average price / night
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Dock and Balcony Serene Big Coppitt Key Escape
Dock and Balcony Serene Big Coppitt Key Escape
House
Key West, FL, USA
1.2k from Shark Key center

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

3 Bedrooms6 Guests
New to Booking
$281
Average price / night
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Home in Blue water Key
Home in Blue water Key
House
Key West, FL, 33040, United States
4.7k from Shark Key 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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Ritaville - Monthly Rental
Ritaville - Monthly Rental
House
Stock Island, FL, USA
3.5k from Shark Key center

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

4 Bedrooms11 Guests
New to Booking
$641
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
5.6k from Shark Key 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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Coral Queen Palm
Coral Queen Palm
House
Key West, FL, USA
5.9k from Shark Key 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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Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!
Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!
House
Key West, FL, 33040, United States
5.8k from Shark Key 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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Waterfront Key West Oasis with Float Dock!
Waterfront Key West Oasis with Float Dock!
House
Key West, FL, USA
6.0k from Shark Key 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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Key West Vacation Home on Canal
Key West Vacation Home on Canal
House
Key West, FL, 33040, United States
9.1k from Shark Key center

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

3 Bedrooms8 Guests
9.8

Exceptional

34 reviews

$290
Average price / night
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Parking Pool Dock - Starboard House
Parking Pool Dock - Starboard House
House
Key West, FL, USA
8.8k from Shark Key center

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

8 Bedrooms20 Guests
New to Booking
$2900
Average price / night
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The Windrose Estate at Lunara Bay
The Windrose Estate at Lunara Bay
House
Key West, FL, 33040, United States
9.1k from Shark Key center

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

6 Bedrooms14 Guests
10.0

Exceptional

6 reviews

$2399
Average price / night
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Parking Pool & Dock - Shellstone House
Parking Pool & Dock - Shellstone House
House
Key West, FL, USA
8.8k from Shark Key center

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

8 Bedrooms16 Guests
New to Booking
$3262
Average price / night
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Luxury 2BR Condo • Oceans Edge Resort, Key West
Luxury 2BR Condo • Oceans Edge Resort, Key West
Condo
Key West, FL, 33040, United States
9.2k from Shark Key center

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

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$676
Average price / night
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The Fairhaven House at Solaire Lunara Bay
The Fairhaven House at Solaire Lunara Bay
House
Key West, FL, USA
8.8k from Shark Key center

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

1 Bedroom16 Guests
New to Booking
$3719
Average price / night
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4 Bed House w/ Heated Pool and Dock - 4 Min. to Key West
4 Bed House w/ Heated Pool and Dock - 4 Min. to Key West
House
Key West, FL, 33040, United States
9.4k from Shark Key center

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

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$675
Average price / night
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The Joyrise House at Solaire Lunara Bay
The Joyrise House at Solaire Lunara Bay
House
Key West, FL, USA
8.8k from Shark Key center

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

1 Bedroom12 Guests
New to Booking
$5185
Average price / night
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 Oceanfront Marina Condo With All Luxuries
Oceanfront Marina Condo With All Luxuries
Condo
Key West, FL, 33040, United States
9.5k from Shark Key center

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

3 Bedrooms6 Guests
9.8

Exceptional

160 reviews

$531
Average price / night
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3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
Condo
Key West, FL, 33040, United States
9.5k from Shark Key center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms8 Guests
10.0

Exceptional

16 reviews

$835
Average price / night
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'Oceanside Oasis' Direct Ocean Views & 3 BR'S
'Oceanside Oasis' Direct Ocean Views & 3 BR'S
Condo
Key West, FL, 33040, United States
9.6k from Shark Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

141 reviews

$516
Average price / night
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Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Apartment
Key West, FL, 33040, United States
9.6k from Shark Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

41 reviews

$654
Average price / night
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Casa Caribe Beautiful tropical 2 bedroom sleeps 6
Casa Caribe Beautiful tropical 2 bedroom sleeps 6
House
Key West, FL, 33040, United States
9.8k from Shark Key center

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

2 Bedrooms6 Guests
10.0

Exceptional

204 reviews

$532
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
9.8k from Shark Key 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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TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
House
Key West, FL, 33040, United States
9.8k from Shark Key center

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

2 Bedrooms4 Guests
10.0

Exceptional

18 reviews

$1032
Average price / night
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Tropical Key West out of the way
Tropical Key West out of the way
House
Key West, FL, 33040, United States
9.9k from Shark Key center

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

3 Bedrooms6 Guests
9.6

Exceptional

188 reviews

$525
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 Shark Key.

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Shark Key Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 61 verified family-friendly vacation rentals in Shark Key. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Shark Key vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $197 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Shark 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 Shark 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 Shark Key often include amenities such as Child Friendly, Balcony/Terrace, and Wellness Facilities. 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.