Family-Friendly Vacation Rentals in The Meadows, FL: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  The Meadows

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604 Best Family Vacation Rentals in The Meadows (Starting from $169)

Meadows Manor
Meadows Manor
House
Key West, FL, USA
0.1k from The Meadows center

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

4 Bedrooms8 Guests
New to Booking
$2500
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
0.1k from The Meadows 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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Keys Please
Keys Please
House
Key West, FL, USA
0.1k from The Meadows center

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

3 Bedrooms6 Guests
New to Booking
$169
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
0.1k from The Meadows 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 Caroline Suite
The Caroline Suite
House
Key West, FL, USA
0.2k from The Meadows center

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

1 Bedroom4 Guests
New to Booking
$316
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
0.2k from The Meadows 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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The Fleming Suite
The Fleming Suite
House
Key West, FL, USA
0.2k from The Meadows center

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

1 Bedroom4 Guests
2.0

Review score

1 reviews

$288
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
0.2k from The Meadows 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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The Elizabeth Suite
The Elizabeth Suite
House
Key West, FL, USA
0.2k from The Meadows center

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

1 Bedroom4 Guests
7.0

Good

1 reviews

$518
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
0.2k from The Meadows 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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Heron Hideaway
Heron Hideaway
Apartment
Key West, FL, USA
0.2k from The Meadows center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Family

1 Bedroom4 Guests
9.3

Superb

6 reviews

$384
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
0.2k from The Meadows 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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Seafarer's Refuge
Seafarer's Refuge
House
Key West, FL, USA
0.2k from The Meadows center

Parking, Child Friendly, Breakfast, Balcony/Terrace, Sports/Activities, Internet, Barbecue/Outdoor Cooking

1 Bedroom10 Guests
New to Booking
$1651
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
0.2k from The Meadows 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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Upper Bayview South
Upper Bayview South
House
Key West, FL, USA
0.2k from The Meadows center

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

1 Bedroom8 Guests
New to Booking
$1259
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
0.2k from The Meadows 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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Sunset North
Sunset North
House
Key West, FL, USA
0.2k from The Meadows center

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

1 Bedroom8 Guests
New to Booking
$1198
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
0.2k from The Meadows 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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Upper Sunset North
Upper Sunset North
House
Key West, FL, USA
0.2k from The Meadows center

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

1 Bedroom8 Guests
New to Booking
$1165
Average price / night
Check Availability
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
0.2k from The Meadows center

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

4 Bedrooms8 Guests
9.8

Exceptional

60 reviews

$1106
Average price / night
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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
0.2k from The Meadows 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
0.2k from The Meadows center

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

2 Bedrooms4 Guests
9.6

Exceptional

68 reviews

$489
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
0.3k from The Meadows 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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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 The Meadows 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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Stunning Historic Estate – 20% Off Summer Bookings, Heated Pool & Bikes Included
Stunning Historic Estate – 20% Off Summer Bookings, Heated Pool & Bikes Included
House
Key West, FL, 33040, United States
0.5k from The Meadows center

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

4 Bedrooms10 Guests
10.0

Exceptional

27 reviews

$562
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
0.5k from The Meadows 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 Most Perfect Old Town Key West Location for a Retreat!
The Most Perfect Old Town Key West Location for a Retreat!
House
Key West, FL, 33040, United States
0.5k from The Meadows center

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

4 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$880
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 The Meadows.

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The Meadows Family Vacation Rentals on the Map

Frequently Asked Questions

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

Prices for family-friendly rentals in The Meadows vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $169 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in The Meadows 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 The Meadows 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 The Meadows often include amenities such as Child Friendly, Pool, 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.