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

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  5.  Key West
  6.  Observation Tower

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993 Beach Home Rentals in Observation Tower (Starting from $279)

La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Resort
Key West, FL, USA
0.2k from Observation Tower center

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

12 Bedrooms31 Guests
8.3

Very Good

54 reviews

$306
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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Opal Key Resort & Marina
Opal Key Resort & Marina
Resort
Key West, FL, USA
0.2k from Observation Tower center

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

188 Bedrooms106 Guests
8.6

Fabulous

1178 reviews

$716
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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Rose Lane Villas
Rose Lane Villas
Villa
Key West, FL, USA
0.2k from Observation Tower center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

10 Bedrooms26 Guests
8.4

Very Good

299 reviews

$345
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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Pier House Resort & Spa
Pier House Resort & Spa
Resort
Key West, FL, USA
0.4k from Observation Tower center

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

140 Bedrooms62 Guests
8.3

Very Good

664 reviews

$534
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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Hyatt Centric Key West Resort & Spa
Hyatt Centric Key West Resort & Spa
Resort
Key West, FL, USA
0.4k from Observation Tower center

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

118 Bedrooms30 Guests
8.2

Very Good

545 reviews

$387
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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Ocean Key Resort & Spa, a Noble House Resort
Ocean Key Resort & Spa, a Noble House Resort
Resort
Key West, FL, USA
0.4k from Observation Tower center

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

97 Bedrooms46 Guests
8.7

Fabulous

116 reviews

$578
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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Garden of Emma by Last Key Realty
Garden of Emma by Last Key Realty
House
Key West, FL, USA
0.5k from Observation Tower center

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

4 Bedrooms8 Guests
New to Booking
$1893
Average price / night
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Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
Condo
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Patio, Pool, TV

2 Bedrooms4 Guests
9.8

Exceptional

154 reviews

$774
Average price / night
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Galleon Resort and Marina
Galleon Resort and Marina
Resort
Observation Tower, Key West, Florida, USA
0.5k from Observation Tower center

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

84 Bedrooms20 Guests
7.1

Good

111 reviews

$603
Average price / night
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Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
Condo
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
9.6

Exceptional

154 reviews

$1012
Average price / night
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Tranquillity Guest House
Tranquillity Guest House
Apartment
Key West, FL, USA
0.6k from Observation Tower center

Apartments, Cheap, Accommodations, Pools, Serviced apartments, 3-star, Lodgings, Places to stay

16 Bedrooms4 Guests
8.2

Very Good

255 reviews

$514
Average price / night
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Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 2 - Downtown Key West
Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 2 - Downtown Key West
Condo
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool

1 Bedroom2 Guests
9.8

Exceptional

48 reviews

$702
Average price / night
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Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.6k from Observation Tower center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

9 Bedrooms28 Guests
9.7

Exceptional

379 reviews

$345
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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The Island Suite at KW Vacation
The Island Suite at KW Vacation
Apartment
Key West, FL, USA
0.6k from Observation Tower center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom4 Guests
9.6

Exceptional

36 reviews

$395
Average price / night
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Bahama Gardens - Main House
Bahama Gardens - Main House
House
Key West, FL, USA
0.6k from Observation Tower center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$2211
Average price / night
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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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Bahama Gardens - Cigar House
Bahama Gardens - Cigar House
House
Key West, FL, USA
0.6k from Observation Tower center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$1058
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
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The Curry Poolside Suite | Second Floor King
The Curry Poolside Suite | Second 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 Bedroom4 Guests
7.4

Good

3 reviews

$474
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 Beach Rentals in Observation Tower.

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Observation Tower Beach Rentals on the Map

Frequently Asked Questions

You can explore 993 verified beach rentals in Observation Tower. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Observation Tower vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $279 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Observation Tower offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Observation Tower welcome pets. Currently, 49 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Observation Tower often include amenities designed for coastal living, such as View, Ocean View, and Oceanfront. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.