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

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  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Observation Tower

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604 Best Family Vacation Rentals in Observation Tower (Starting from $250)

Darling of Duval by Last Key Realty
Darling of Duval by Last Key Realty
House
Key West, FL, USA
0.0k from Observation Tower center

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

2 Bedrooms4 Guests
New to Booking
$929
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
0.1k from Observation Tower 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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New The Cottage at James House
New The Cottage at James House
House
Key West, FL, USA
0.1k from Observation Tower center

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

1 Bedroom3 Guests
8.8

Fabulous

6 reviews

$358
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
0.3k from Observation Tower 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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Sailfish Suite on Duval
Sailfish Suite on Duval
Apartment
Key West, FL, USA
0.1k from Observation Tower center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$629
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
0.3k from Observation Tower 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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Last Minute
Last Minute
House
Key West, FL, USA
0.1k from Observation Tower center

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

3 Bedrooms6 Guests
8.0

Good

2 reviews

$1115
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
0.3k from Observation Tower 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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New Rose Retreat - Pool & Parking
New Rose Retreat - Pool & Parking
House
FL, USA
0.2k from Observation Tower center

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

2 Bedrooms6 Guests
New to Booking
$1180
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
0.4k from Observation Tower 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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New Rose Petal Petite Suite - Pool & Parking
New Rose Petal Petite Suite - Pool & Parking
Apartment
FL, USA
0.2k from Observation Tower center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom2 Guests
7.0

Good

1 reviews

$324
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
0.4k from Observation Tower 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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New Coastal Rose - Bright Loft with High Ceilings
New Coastal Rose - Bright Loft with High Ceilings
Apartment
FL, USA
0.2k from Observation Tower center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom4 Guests
7.3

Good

3 reviews

$427
Average price / night
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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
0.4k from Observation Tower 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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Rigby House - Brand New with Private Pool
Rigby House - Brand New with Private Pool
House
Key West, FL, USA
0.2k from Observation Tower center

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

6 Bedrooms12 Guests
New to Booking
$2937
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
0.4k from Observation Tower 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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Trumans Trove by Last Key realty
Trumans Trove by Last Key realty
House
Key West, FL, USA
0.2k from Observation Tower center

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

2 Bedrooms6 Guests
New to Booking
$946
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 Observation Tower 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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Jasmine Jule by Last Key Realty
Jasmine Jule by Last Key Realty
House
Key West, FL, USA
0.2k from Observation Tower center

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

2 Bedrooms6 Guests
New to Booking
$4329
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
0.5k from Observation Tower 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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Underwater Cabana at Custom House Inn
Underwater Cabana at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Observation Tower center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$481
Average price / night
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Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Villa
Key West, FL, 33040, United States
0.5k from Observation Tower center

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

3 Bedrooms7 Guests
New to Booking
$1047
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
0.5k from Observation Tower center

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

3 Bedrooms6 Guests
New to Booking
$483
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 Observation Tower center

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

1 Bedroom2 Guests
New to Booking
$450
Average price / night
Check Availability
Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
Condo
Key West, FL, 33040, United States
0.5k from Observation Tower center

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

2 Bedrooms4 Guests
10.0

Exceptional

232 reviews

$250
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
0.5k from Observation Tower 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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Palm Trees Ocean Breeze Key West FL
Palm Trees Ocean Breeze Key West FL
House
Key West, FL, 33040, United States
0.5k from Observation Tower center

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

3 Bedrooms8 Guests
9.4

Superb

43 reviews

$1190
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 Observation Tower.

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Frequently Asked Questions

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

Prices for family-friendly rentals in Observation Tower vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $250 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Observation Tower 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 Observation Tower 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 Observation Tower often include amenities such as Child Friendly, Pool, and Wellness Facilities. 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.