Family-Friendly Vacation Rentals in Mallory Square, FL: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Mallory Square

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604 Best Family Vacation Rentals in Mallory Square (Starting from $279)

Luxury 4BDR/4BA Penthouse
Luxury 4BDR/4BA Penthouse
House
Key West, FL, USA
0.1k from Mallory Square center

Laundry, Security/Safety, Child Friendly

4 Bedrooms8 Guests
New to Booking
$977
Average price / night
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Heart of Key West - 2BR Waterfront at the Galleon Resort
Heart of Key West - 2BR Waterfront at the Galleon Resort
Condo
Key West, FL, 33040, United States
0.4k from Mallory Square center

AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$784
Average price / night
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Harbor Luxe Celebration Suites
Harbor Luxe Celebration Suites
Apartment
Key West, FL, USA
0.1k from Mallory Square center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom20 Guests
New to Booking
$3894
Average price / night
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Amsterdam's Curry Mansion Inn
Amsterdam's Curry Mansion Inn
House
511 Caroline St, Key West, FL, 33040, United States
0.4k from Mallory Square center

AC, Business Services, Elevator, Heater, Internet, Laundry, Outdoor Space, Pool, TV

8.2

Very Good

1004 reviews

$279
Average price / night
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Underwater Cabana at Custom House Inn
Underwater Cabana at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$481
Average price / night
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SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
Condo
Key West, FL, 33040, United States
0.4k from Mallory Square center

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

2 Bedrooms6 Guests
8.0

Good

1 reviews

$894
Average price / night
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Chicken Run at Custom House Inn
Chicken Run at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$514
Average price / night
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The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
Condo
Key West, FL, 33040, United States
0.4k from Mallory Square center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub

2 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$853
Average price / night
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Citrus Queen at Custom House Inn
Citrus Queen at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$544
Average price / night
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Birds of a Feather at Custom House Inn
Birds of a Feather at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$549
Average price / night
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Chicken Water Cabana at Custom House Inn
Chicken Water Cabana at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$837
Average price / night
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Feather Queen at Custom House Inn
Feather Queen at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$867
Average price / night
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Truman Annex end-unit home, private outdoor spaces, pool, close to Duval & beach
Truman Annex end-unit home, private outdoor spaces, pool, close to Duval & beach
House
Key West, FL, 33040, United States
0.5k from Mallory Square center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

23 reviews

$346
Average price / night
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Sunshine State at Custom House Inn
Sunshine State at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom3 Guests
New to Booking
$541
Average price / night
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Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
Condo
Key West, FL, 33040, United States
0.5k from Mallory Square center

AC, Barbecue, Elevator, Fitness Equipment, Heater, Hot Tub, Internet, Kitchen, Microwave

1 Bedroom2 Guests
New to Booking
$450
Average price / night
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Custom House Inn All
Custom House Inn All
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Accommodations, Lodgings, Places to stay

8 Bedrooms25 Guests
New to Booking
$5685
Average price / night
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Hemingway Hideaway in the Truman Annex
Hemingway Hideaway in the Truman Annex
House
Key West, FL, 33040, United States
0.5k from Mallory Square center

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

2 Bedrooms6 Guests
9.8

Exceptional

68 reviews

$469
Average price / night
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The Penthouse at Custom House Inn
The Penthouse at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Mallory Square center

Apartments, Accommodations, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$919
Average price / night
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PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
House
Key West, FL, 33040, United States
0.6k from Mallory Square center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.8

Exceptional

37 reviews

$2591
Average price / night
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Luxe Designer Oasis + Guest House steps off Duval
Luxe Designer Oasis + Guest House steps off Duval
House
Key West, FL, 33040, United States
0.7k from Mallory Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, Living Area

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1050
Average price / night
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Luxury Truman Annex Condo I 3BDR I Pool & Parking I Walk to Duval & Beach
Luxury Truman Annex Condo I 3BDR I Pool & Parking I Walk to Duval & Beach
Condo
Key West, FL, 33040, United States
0.7k from Mallory Square center

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

3 Bedrooms6 Guests
New to Booking
$483
Average price / night
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Palm Trees Ocean Breeze Key West FL
Palm Trees Ocean Breeze Key West FL
House
Key West, FL, 33040, United States
0.7k from Mallory Square center

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

3 Bedrooms8 Guests
9.4

Superb

43 reviews

$1190
Average price / night
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Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
House
Key West, FL, 33040, United States
0.7k from Mallory Square center

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

3 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$399
Average price / night
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Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
House
Key West, FL, 33040, United States
0.7k from Mallory Square center

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

3 Bedrooms4 Guests
9.2

Superb

50 reviews

$296
Average price / night
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Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
House
Key West, FL, 33040, United States
0.7k from Mallory Square center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$532
Average price / night
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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 Mallory Square.

Where to stay in Mallory Square? Best neighborhoods & areas

Mallory Square Family Vacation Rentals on the Map

Frequently Asked Questions

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

Prices for family-friendly rentals in Mallory Square vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $279 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Mallory Square 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 Mallory Square 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 Mallory Square often include amenities such as Child Friendly, Laundry, and Bedding/Linens. 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.