Family-Friendly Vacation Rentals in Flagler Station Oversea Railway Historeum, FL: Compare 10+ Sites & Save

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604 Best Family Vacation Rentals in Flagler Station Oversea Railway Historeum (Starting from $198)

Kokomo Suite by Last Key Realty
Kokomo Suite by Last Key Realty
House
Key West, FL, USA
0.2k from Flagler Station Oversea Railway Historeum center

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

1 Bedroom2 Guests
New to Booking
$488
Average price / night
Check Availability
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
0.2k from Flagler Station Oversea Railway Historeum 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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Barbuda Suite by Last Key Realty
Barbuda Suite by Last Key Realty
House
Key West, FL, USA
0.2k from Flagler Station Oversea Railway Historeum center

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

1 Bedroom4 Guests
New to Booking
$632
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
0.2k from Flagler Station Oversea Railway Historeum 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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Calusa Suite by Last Key Realty
Calusa Suite by Last Key Realty
House
Key West, FL, USA
0.2k from Flagler Station Oversea Railway Historeum center

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

1 Bedroom2 Guests
New to Booking
$465
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
0.2k from Flagler Station Oversea Railway Historeum 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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Key West Holidays
Key West Holidays
House
Key West, FL, USA
0.2k from Flagler Station Oversea Railway Historeum center

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

4 Bedrooms10 Guests
New to Booking
$496
Average price / night
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The Gideon Lowe House - Old Town Key West
The Gideon Lowe House - Old Town Key West
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$785
Average price / night
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Lazy Gecko by AvantStay Walk to Duval St in Key West Month Long Stays Only
Lazy Gecko by AvantStay Walk to Duval St in Key West Month Long Stays Only
House
Key West, FL, USA
0.2k from Flagler Station Oversea Railway Historeum center

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

1 Bedroom4 Guests
New to Booking
$198
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
0.3k from Flagler Station Oversea Railway Historeum 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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Key Lime Pie by AvantStay Ideal Location w Splash Pool Out Door Dining Month Long Stays Only
Key Lime Pie by AvantStay Ideal Location w Splash Pool Out Door Dining Month Long Stays Only
House
Key West, FL, USA
0.2k from Flagler Station Oversea Railway Historeum center

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

2 Bedrooms4 Guests
New to Booking
$273
Average price / night
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FLEMING-O (Flamingo) Cottage is the perfect getaway
FLEMING-O (Flamingo) Cottage is the perfect getaway
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

AC, Barbecue, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Grill

2 Bedrooms6 Guests
10.0

Exceptional

134 reviews

$574
Average price / night
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Star of the Seaport by Last Key Realty
Star of the Seaport by Last Key Realty
House
Key West, FL, USA
0.3k from Flagler Station Oversea Railway Historeum center

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

5 Bedrooms12 Guests
New to Booking
$2584
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
0.5k from Flagler Station Oversea Railway Historeum 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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THE GATO ROOM at Inn on Fleming Key West!
THE GATO ROOM at Inn on Fleming Key West!
House
Key West, FL, USA
0.3k from Flagler Station Oversea Railway Historeum 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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Secret Villa I @ Old Town with Private Pool, close to Duval!
Secret Villa I @ Old Town with Private Pool, close to Duval!
Villa
Key West, FL, 33040, United States
0.5k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
10.0

Exceptional

175 reviews

$1293
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
0.3k from Flagler Station Oversea Railway Historeum center

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

1 Bedroom4 Guests
New to Booking
$576
Average price / night
Check Availability
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Villa
Key West, FL, 33040, United States
0.5k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
10.0

Exceptional

157 reviews

$1265
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
0.3k from Flagler Station Oversea Railway Historeum center

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

1 Bedroom2 Guests
New to Booking
$474
Average price / night
Check Availability
Amsterdam's Curry Mansion Inn
Amsterdam's Curry Mansion Inn
House
511 Caroline St, Key West, FL, 33040, United States
0.5k from Flagler Station Oversea Railway Historeum 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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THE FLAGLER ROOM at Inn on Fleming Key West!
THE FLAGLER ROOM at Inn on Fleming Key West!
House
Key West, FL, USA
0.3k from Flagler Station Oversea Railway Historeum center

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

1 Bedroom2 Guests
New to Booking
$249
Average price / night
Check Availability
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 Flagler Station Oversea Railway Historeum center

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

1 Bedroom2 Guests
New to Booking
$450
Average price / night
Check Availability
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
Condo
Key West, FL, 33040, United States
0.5k from Flagler Station Oversea Railway Historeum center

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

2 Bedrooms6 Guests
8.0

Good

1 reviews

$894
Average price / night
Check Availability
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
0.5k from Flagler Station Oversea Railway Historeum 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
Check Availability
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
0.6k from Flagler Station Oversea Railway Historeum center

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

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$483
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 Flagler Station Oversea Railway Historeum.

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Frequently Asked Questions

You can explore 604 verified family-friendly vacation rentals in Flagler Station Oversea Railway Historeum. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Flagler Station Oversea Railway Historeum vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $198 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Flagler Station Oversea Railway Historeum 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 Flagler Station Oversea Railway Historeum 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 Flagler Station Oversea Railway Historeum often include amenities such as Child Friendly, Pool, and Internet. 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.