Family-Friendly Hotels in The Oldest House - Key West, FL

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64 Family-Friendly Hotels in The Oldest House - Key West (From $304)

The Key West Hotel
The Key West Hotel
Hotel
Key West, FL, USA
0.1k from The Oldest House - Key West center

Cheap, Accommodations, Pools, Pet-friendly, 3-star, Lodgings, Places to stay, Family

10.0

Exceptional

1 reviews

$420
Average price / night
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Southwinds Motel
Southwinds Motel
Hotel
1321 Simonton Street, Key West, FL, 33040, United States
1.4k from The Oldest House - Key West center

AC, Bar, Breakfast Included, Crib, Frontdesk 24 Hour, Laundry, Microwave, Outdoor Space, Parking Available

8.6

Fabulous

1298 reviews

$304
Average price / night
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Blue Room at the Grand Maloney
Blue Room at the Grand Maloney
Hotel
Key West, FL, USA
0.1k from The Oldest House - Key West center

B&bs, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

9.3

Superb

3 reviews

$403
Average price / night
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Margaritaville Beach House Key West
Margaritaville Beach House Key West
Hotel
2001 South Roosevelt Boulevard, Key West, FL, 33040, United States
3.3k from The Oldest House - Key West center

AC, Bar, Breakfast Available, Business Services, Crib, Elevator, Fitness Equipment, Frontdesk 24 Hour, Housekeeping

8.8

Fabulous

1805 reviews

$349
Average price / night
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Yellow Room at Grand Maloney
Yellow Room at Grand Maloney
Hotel
Key West, FL, USA
0.1k from The Oldest House - Key West center

B&bs, Accommodations, Pools, Inns, Lodgings, Places to stay

5.0

Review score

1 reviews

$551
Average price / night
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Celebrate New Years Eve in Key West @ Exclusive Hyatt Windward - SLEEPS 6 !
Celebrate New Years Eve in Key West @ Exclusive Hyatt Windward - SLEEPS 6 !
Resort
Key West, FL, 33040, United States
5.3k from The Oldest House - Key West center

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

10.0

Exceptional

1 reviews

$2193
Average price / night
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Green Room at the Grand Maloney
Green Room at the Grand Maloney
Hotel
Key West, FL, USA
0.1k from The Oldest House - Key West center

B&bs, Cheap, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

8.5

Very Good

4 reviews

$429
Average price / night
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𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Dream Getaway at the Beach House Resort+Amenities. 2BR
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Dream Getaway at the Beach House Resort+Amenities. 2BR
Resort
Key West, FL, 33040, United States
5.4k from The Oldest House - Key West center

AC, Arcade, Balcony, Barbecue, Crib, Fitness Equipment, Free Parking, Hot Tub, Internet

New to Booking
$752
Average price / night
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Carriage House at Grand Maloney
Carriage House at Grand Maloney
Hotel
Key West, FL, USA
0.1k from The Oldest House - Key West center

B&bs, Accommodations, Pools, Parking, Inns, Lodgings, Places to stay

New to Booking
$403
Average price / night
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Hyatt Windward Pointe, 2 Bedroom Waterfront Resort, 4-Night May 3-7
Hyatt Windward Pointe, 2 Bedroom Waterfront Resort, 4-Night May 3-7
Resort
Key West, FL, 33040, United States
5.6k from The Oldest House - Key West center

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

9.6

Exceptional

4 reviews

$365
Average price / night
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Bunk Room at the Grand Maloney
Bunk Room at the Grand Maloney
Hotel
Key West, FL, USA
0.1k from The Oldest House - Key West center

B&bs, Cheap, Accommodations, Pools, Inns, Lodgings, Places to stay, Family

9.7

Exceptional

3 reviews

$402
Average price / night
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Key Lime Cottage
Key Lime Cottage
Hotel
Key West, FL, USA
0.1k from The Oldest House - Key West center

B&bs, Accommodations, Pools, Parking, Inns, Cottages, Pet-friendly, Lodgings, Vacation rentals

4.0

Review score

1 reviews

$638
Average price / night
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Sugar Pie Suite
Sugar Pie Suite
Hotel
Key West, FL, USA
0.1k from The Oldest House - Key West center

B&bs, Accommodations, Pools, Inns, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

3.5

Review score

2 reviews

$621
Average price / night
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La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Resort
Key West, FL, USA
0.2k from The Oldest House - Key West center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

8.3

Very Good

54 reviews

$306
Average price / night
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Ridley House - Key West Historic Inns
Ridley House - Key West Historic Inns
Hotel
Key West, FL, USA
0.2k from The Oldest House - Key West center

B&bs, Cheap, Accommodations, Pools, Inns, Pet-friendly, 3-star, Lodgings, Places to stay

8.8

Fabulous

215 reviews

$377
Average price / night
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Opal Key Resort & Marina
Opal Key Resort & Marina
Resort
Key West, FL, USA
0.3k from The Oldest House - Key West center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Hot tubs

8.6

Fabulous

1178 reviews

$716
Average price / night
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Hyatt Vacation Club at Sunset Harbor
Hyatt Vacation Club at Sunset Harbor
Hotel
Key West, FL, USA
0.3k from The Oldest House - Key West center

Accommodations, Parking, 4-star, Lodgings, Places to stay, Self-catering, Accessible hotels

8.2

Very Good

173 reviews

$323
Average price / night
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Pier House Resort & Spa
Pier House Resort & Spa
Resort
Key West, FL, USA
0.4k from The Oldest House - Key West center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 4-star, Lodgings

8.3

Very Good

664 reviews

$534
Average price / night
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Pegasus International Hotel
Pegasus International Hotel
Hotel
The Oldest House - Key West, Key West, Florida, USA
0.4k from The Oldest House - Key West center

Accommodations, Pools, Parking, 3-star, Lodgings, Jacuzzis, Places to stay

7.5

Good

1269 reviews

$460
Average price / night
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Hyatt Centric Key West Resort & Spa
Hyatt Centric Key West Resort & Spa
Resort
Key West, FL, USA
0.4k from The Oldest House - Key West center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 4-star, Lodgings

8.2

Very Good

545 reviews

$387
Average price / night
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Ocean Key Resort & Spa, a Noble House Resort
Ocean Key Resort & Spa, a Noble House Resort
Resort
Key West, FL, USA
0.4k from The Oldest House - Key West center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, 4-star, Lodgings, Jacuzzis

8.7

Fabulous

116 reviews

$578
Average price / night
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Pro Tip for Travelers:
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The Oldest House - Key West Family-Friendly Hotels on the Map

Frequently Asked Questions

Family-friendly hotels in The Oldest House - Key West often offer spacious rooms, kid-friendly amenities, and on-site activities. Features like pools, play areas, and family suites can make your stay more comfortable.

Yes, you can find 64 family-friendly hotels in The Oldest House - Key West with prices starting from around $304 per night, depending on travel dates and room size.

Many properties cater to families with services such as babysitting, kids’ clubs, or child-friendly dining options. Availability may vary by hotel.

Booking early is recommended during school holidays and peak travel seasons. This ensures better room availability and access to family-oriented amenities.

Yes, many family-friendly hotels in The Oldest House - Key West offer connecting rooms, suites, or multi-bedroom accommodations designed for larger groups.