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

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  5.  Key West
  6.  Observation Tower

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1736 Best Vacation Rentals in Observation Tower (Starting from $279)

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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**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Cottage
Key West, FL, 33040, United States
0.0k from Observation Tower center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

152 reviews

$966
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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Shared Pool & Parking - The Cottage at James House
Shared Pool & Parking - The Cottage at James House
House
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

1 Bedroom3 Guests
8.8

Fabulous

9 reviews

$555
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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Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
Apartment
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Internet, Kitchen, Microwave, No Smoking, Pool, TV

2 Bedrooms6 Guests
9.6

Exceptional

31 reviews

$726
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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Pilar Cottage | Spectacular Studio w/ Shared Pool
Pilar Cottage | Spectacular Studio w/ Shared Pool
Apartment
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Internet, Living Area, Microwave, No Smoking, Pool, TV

1 Bedroom4 Guests
9.0

Fabulous

14 reviews

$460
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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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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The Penthouse at Custom House Inn | New!
The Penthouse at Custom House Inn | New!
Apartment
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Internet, Kitchen, Living Area, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

23 reviews

$1174
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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Cabana on Duval  |  Monthly studio w/ shared pool
Cabana on Duval | Monthly studio w/ shared pool
Apartment
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Dryer, Internet, Microwave, No Smoking, TV, Washer

New to Booking
$324
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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Orchid Suite on Duval
Orchid Suite on Duval
Apartment
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Internet, Kitchen, Microwave, No Smoking, TV

New to Booking
$327
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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Spacious home with pool & balcony - 1 block from Duval Street
Spacious home with pool & balcony - 1 block from Duval Street
House
Key West, FL, 33040, United States
0.1k from Observation Tower center

3 Bedrooms6 Guests
New to Booking
$913
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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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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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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**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Observation Tower center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$730
Average price / night
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Chicken Run at Custom House Inn
Chicken Run at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Observation Tower center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$514
Average price / night
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The Curry Poolside | Ground  Floor King
The Curry Poolside | Ground Floor King
Apartment
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Dryer, Internet, Laundry, No Smoking, Outdoor Space, Pool, TV

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$451
Average price / night
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Citrus Queen at Custom House Inn
Citrus Queen 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
$544
Average price / night
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Birds of a Feather at Custom House Inn
Birds of a Feather 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
$549
Average price / night
Check Availability
The Curry Poolside | Ground Floor Two Queens
The Curry Poolside | Ground Floor Two Queens
Apartment
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Dryer, Internet, Laundry, No Smoking, Outdoor Space, Pool, TV

1 Bedroom4 Guests
9.2

Superb

5 reviews

$461
Average price / night
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The Curry Poolside | Second Floor King
The Curry Poolside | Second Floor King
Apartment
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Dryer, Extra Bed, Free Parking, Internet, Laundry, No Smoking, Outdoor Space

1 Bedroom2 Guests
8.0

Good

3 reviews

$551
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 Vacation Rentals in Observation Tower.

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Frequently Asked Questions

You can explore 1736 verified vacation rentals in Observation Tower. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Observation Tower vary depending on the season, property size, and location. Rates typically start from around $279 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Observation Tower include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Observation Tower welcome pets. Currently, 44 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Observation Tower often include amenities such as Security/Safety, Internet, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.