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

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  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Midtown

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604 Best Family Vacation Rentals in Midtown (Starting from $223)

Flagler Station
Flagler Station
House
Key West, FL, USA
0.3k from Midtown center

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

3 Bedrooms6 Guests
New to Booking
$408
Average price / night
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BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
House
Key West, FL, 33040, United States
0.1k from Midtown center

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

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$470
Average price / night
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Plantation Tropicale by Last Key Realty
Plantation Tropicale by Last Key Realty
House
Key West, FL, USA
0.4k from Midtown center

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

5 Bedrooms12 Guests
New to Booking
$2964
Average price / night
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ISLAND SANCTUARY KEY WEST - 3 Bedroom / 2 Bathroom with Pool and Parking!
ISLAND SANCTUARY KEY WEST - 3 Bedroom / 2 Bathroom with Pool and Parking!
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

3 Bedrooms6 Guests
New to Booking
$327
Average price / night
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Casa de Sunshine
Casa de Sunshine
House
Key West, FL, USA
0.5k from Midtown center

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

2 Bedrooms4 Guests
New to Booking
$358
Average price / night
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SOUTHERNMOST SWIM AND SOCIAL CLUB
SOUTHERNMOST SWIM AND SOCIAL CLUB
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$720
Average price / night
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Belle of the Beach by Last Key Realty
Belle of the Beach by Last Key Realty
House
Key West, FL, USA
0.5k from Midtown center

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

6 Bedrooms16 Guests
New to Booking
$2390
Average price / night
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Gorgeous beach bungalow just steps from the beach!
Gorgeous beach bungalow just steps from the beach!
House
Key West, FL, 33040, United States
0.3k from Midtown center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$223
Average price / night
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Sunshine Drive
Sunshine Drive
House
Key West, FL, USA
0.5k from Midtown center

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

3 Bedrooms10 Guests
New to Booking
$391
Average price / night
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The Secret Grotto
The Secret Grotto
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

4 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$611
Average price / night
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Sundial on the Atlantic Ocean View
Sundial on the Atlantic Ocean View
House
FL, USA
0.6k from Midtown center

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

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$870
Average price / night
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Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
House
Key West, FL, 33040, United States
0.4k from Midtown center

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

3 Bedrooms8 Guests
6.8

Good

3 reviews

$699
Average price / night
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Ocean View
Ocean View
House
Key West, FL, USA
0.6k from Midtown center

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

2 Bedrooms6 Guests
New to Booking
$901
Average price / night
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BE AS YOU ARE - 3 Bedroom / 3 Bathroom - Mid Town KEY WEST w/ POOL
BE AS YOU ARE - 3 Bedroom / 3 Bathroom - Mid Town KEY WEST w/ POOL
House
Key West, FL, 33040, United States
0.4k from Midtown center

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

3 Bedrooms6 Guests
New to Booking
$607
Average price / night
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Banyan Suite
Banyan Suite
Apartment
Key West, FL, USA
0.6k from Midtown center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$337
Average price / night
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Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
House
Key West, FL, 33040, United States
0.5k from Midtown center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Dryer, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$557
Average price / night
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Palm Suite
Palm Suite
Apartment
Key West, FL, USA
0.6k from Midtown center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$316
Average price / night
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OFF THE HOOK - 3 Bedroom / 3 Bathroom W/ Pool & Parking
OFF THE HOOK - 3 Bedroom / 3 Bathroom W/ Pool & Parking
House
Key West, FL, 33040, United States
0.5k from Midtown center

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

3 Bedrooms7 Guests
9.2

Superb

5 reviews

$307
Average price / night
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Atlantic Reflections by Last Key Realty
Atlantic Reflections by Last Key Realty
Apartment
Key West, FL, USA
0.6k from Midtown center

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

2 Bedrooms6 Guests
New to Booking
$1286
Average price / night
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 4-bedroom New Construction house with private pool in Key West
4-bedroom New Construction house with private pool in Key West
House
Key West, FL, 33040, United States
0.6k from Midtown center

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

4 Bedrooms8 Guests
New to Booking
$778
Average price / night
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Luxury High End, 2 Bikes,  Highspeed Wi-Fi, Work station,  Pool, Hot Tub, Gym
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Condo
Key West, FL, 33040, United States
0.6k from Midtown center

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

1 Bedroom4 Guests
9.8

Exceptional

311 reviews

$490
Average price / night
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Flirty Flamingo Key West
Flirty Flamingo Key West
House
Key West, FL, 33040, United States
0.6k from Midtown center

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

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$444
Average price / night
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Sea Breeze at 1800 Atlantic
Sea Breeze at 1800 Atlantic
Condo
Key West, FL, 33040, United States
0.6k from Midtown center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
8.8

Fabulous

5 reviews

$276
Average price / night
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Oceanview at 1800 Atlantic, short walk to Smathers Beach wish Island Paradise
Oceanview at 1800 Atlantic, short walk to Smathers Beach wish Island Paradise
Condo
Key West, FL, 33040, United States
0.7k from Midtown center

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

2 Bedrooms6 Guests
9.2

Superb

21 reviews

$528
Average price / night
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Penthouse Beach Ocean Views-  Live the Dream
Penthouse Beach Ocean Views- Live the Dream
Condo
Key West, FL, 33040, United States
0.7k from Midtown center

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

2 Bedrooms6 Guests
9.8

Exceptional

257 reviews

$731
Average price / night
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Beach Penthouse: Ocean Views from every room  Tropical Excellence
Beach Penthouse: Ocean Views from every room Tropical Excellence
Condo
Key West, FL, 33040, United States
0.7k from Midtown center

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

2 Bedrooms6 Guests
9.8

Exceptional

227 reviews

$718
Average price / night
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Panoramic Ocean: Beach from every window
Panoramic Ocean: Beach from every window
Condo
Key West, FL, 33040, United States
0.7k from Midtown center

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

2 Bedrooms6 Guests
9.8

Exceptional

333 reviews

$751
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 Midtown.

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Midtown Family Vacation Rentals on the Map

Frequently Asked Questions

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

Prices for family-friendly rentals in Midtown vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $223 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Midtown 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 Midtown 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 Midtown often include amenities such as Child Friendly, Pool, and Fireplace/Heating. 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.