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

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604 Best Family Vacation Rentals in Studios of Key West (Starting from $203)

Casa Serendipity by Last Key Realty
Casa Serendipity by Last Key Realty
House
Key West, FL, USA
0.1k from Studios of Key West center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$809
Average price / night
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BOTTOMS UP BUNGALOW - PERFECT  2 Bed/2 Bath PRIVATE POOL
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
House
Key West, FL, 33040, United States
0.3k from Studios of Key West center

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

2 Bedrooms6 Guests
10.0

Exceptional

121 reviews

$1546
Average price / night
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THE GATO ROOM at Inn on Fleming Key West!
THE GATO ROOM at Inn on Fleming Key West!
House
Key West, FL, USA
0.2k from Studios of Key West center

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

1 Bedroom2 Guests
New to Booking
$289
Average price / night
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Key West Cottage Located in Old Town Key West. Available February 2026-on!!!!
Key West Cottage Located in Old Town Key West. Available February 2026-on!!!!
House
Key West, FL, 33040, United States
0.3k from Studios of Key West center

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

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$483
Average price / night
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THE CORNISH SUITE at Inn on Fleming Key West!
THE CORNISH SUITE at Inn on Fleming Key West!
House
Key West, FL, USA
0.2k from Studios of Key West center

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

1 Bedroom4 Guests
New to Booking
$576
Average price / night
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MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
House
Key West, FL, 33040, United States
0.4k from Studios of Key West center

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

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$774
Average price / night
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THE SIMONTON ROOM at Inn on Fleming Key West
THE SIMONTON ROOM at Inn on Fleming Key West
House
Key West, FL, USA
0.2k from Studios of Key West center

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

1 Bedroom2 Guests
New to Booking
$474
Average price / night
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Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
House
Key West, FL, 33040, United States
0.4k from Studios of Key West center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$489
Average price / night
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THE FLAGLER ROOM at Inn on Fleming Key West!
THE FLAGLER ROOM at Inn on Fleming Key West!
House
Key West, FL, USA
0.2k from Studios of Key West center

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

1 Bedroom2 Guests
New to Booking
$249
Average price / night
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Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
House
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

2 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$344
Average price / night
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THE GEIGER SUITE at Inn on Fleming Key West!
THE GEIGER SUITE at Inn on Fleming Key West!
House
Key West, FL, USA
0.2k from Studios of Key West center

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

1 Bedroom4 Guests
8.0

Good

1 reviews

$592
Average price / night
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Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
House
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

3 Bedrooms8 Guests
9.8

Exceptional

138 reviews

$1393
Average price / night
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THE MALLORY SUITE at Inn on Fleming Key West!
THE MALLORY SUITE at Inn on Fleming Key West!
Apartment
Key West, FL, USA
0.2k from Studios of Key West center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom2 Guests
9.0

Fabulous

1 reviews

$327
Average price / night
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3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

3 Bedrooms6 Guests
9.6

Exceptional

81 reviews

$993
Average price / night
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Petronia Cottage
Petronia Cottage
House
Key West, FL, USA
0.2k from Studios of Key West center

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

2 Bedrooms4 Guests
New to Booking
$322
Average price / night
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4-Bed, 3-Bath Waterfront Condo at Bayfront Suites -CLEANING FEE INCLUDED
4-Bed, 3-Bath Waterfront Condo at Bayfront Suites -CLEANING FEE INCLUDED
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

4 Bedrooms8 Guests
9.0

Fabulous

68 reviews

$1160
Average price / night
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Authors Key West Guesthouse
Authors Key West Guesthouse
House
Studios of Key West, Key West, Florida, USA
0.2k from Studios of Key West center

B&bs, Accommodations, Pools, Guest houses, Homestays, Lodgings, Vacation rentals, Jacuzzis, Places to stay

16 Bedrooms34 Guests
8.3

Very Good

1330 reviews

$798
Average price / night
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4-Bed 4.5 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED Non-Waterfront
4-Bed 4.5 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED Non-Waterfront
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

4 Bedrooms8 Guests
9.6

Exceptional

98 reviews

$1145
Average price / night
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Land Of Love by AvantStay Pets Allowed Shared Pool Great Location Month Long Stays Only
Land Of Love by AvantStay Pets Allowed Shared Pool Great Location Month Long Stays Only
House
Key West, FL, USA
0.2k from Studios of Key West center

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

1 Bedroom4 Guests
New to Booking
$227
Average price / night
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Waterfront 3-Bedroom Condo at Bayfront Suites & Marina- CLEANING FEE INCLUDED
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina- CLEANING FEE INCLUDED
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

3 Bedrooms6 Guests
9.6

Exceptional

93 reviews

$960
Average price / night
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Breezy Key West First-Floor Condo with Pool Access
Breezy Key West First-Floor Condo with Pool Access
Apartment
Key West, FL, USA
0.3k from Studios of Key West center

Apartments, Accommodations, Parking, Spa, Lodgings, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$203
Average price / night
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4-Bed, 4.5 Bath Condo & Bayfront Suites-non waterfront CLEANING FEE INCLUDED
4-Bed, 4.5 Bath Condo & Bayfront Suites-non waterfront CLEANING FEE INCLUDED
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

4 Bedrooms8 Guests
9.8

Exceptional

128 reviews

$1235
Average price / night
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Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites - CLEANING FEE INCLUDED
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites - CLEANING FEE INCLUDED
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

4 Bedrooms8 Guests
9.6

Exceptional

104 reviews

$1147
Average price / night
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3 Bed 3 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED (Non-Waterfront)
3 Bed 3 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED (Non-Waterfront)
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

3 Bedrooms6 Guests
9.6

Exceptional

77 reviews

$968
Average price / night
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Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

4 Bedrooms8 Guests
9.8

Exceptional

60 reviews

$1106
Average price / night
Check Availability
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

4 Bedrooms8 Guests
9.8

Exceptional

79 reviews

$1300
Average price / night
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2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
Condo
Key West, FL, 33040, United States
0.5k from Studios of Key West center

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

2 Bedrooms4 Guests
9.6

Exceptional

68 reviews

$489
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 Studios of Key West.

Where to stay in Studios of Key West? Best neighborhoods & areas

Studios of Key West Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 604 verified family-friendly vacation rentals in Studios of Key West. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Studios of Key West vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $203 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Studios of Key West 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 Studios of Key West 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 Studios of Key West often include amenities such as Child Friendly, View, 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.