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

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Observation Tower

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1053 Best Oceanfront Rentals in Observation Tower (Starting from $306)

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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**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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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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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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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 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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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 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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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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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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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 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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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 - 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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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 Oceanfront Rentals in Observation Tower.

Where to stay in Observation Tower? Best neighborhoods & areas

Observation Tower Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1053 verified oceanfront rentals in Observation Tower. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Observation Tower vary depending on the property size, exact beachfront location, and season. Rates typically start from around $306 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Observation Tower offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Observation Tower welcome pets. Currently, 51 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Observation Tower often include features designed for a comfortable coastal stay, such as Oceanfront, View, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.