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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Observation Tower

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1469 Best Vacation Rentals with Pool 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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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 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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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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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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**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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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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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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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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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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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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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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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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\"Island Time\" in Old Town
\"Island Time\" in Old Town
House
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Dryer, Internet, Kitchen, Laundry, No Smoking, Pool, TV, Washer

2 Bedrooms4 Guests
New to Booking
$390
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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The Key West Hotel
The Key West Hotel
House
325 Duval St., Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Housekeeping, Internet, Outdoor Space, Pets, Pool, Room Service, TV

9.2

Superb

547 reviews

$490
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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Conch House at the Truman Annex in Key West
Conch House at the Truman Annex in Key West
House
Key West, FL, 33040, United States
0.1k from Observation Tower center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$623
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 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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3 Bedroom Key West Home - Perfect Location & Private Pool
3 Bedroom Key West Home - Perfect Location & Private Pool
House
Key West, FL, 33040, United States
0.2k from Observation Tower center

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

3 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$1394
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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Rose Key Cottage - Private Pool & Near Duval
Rose Key Cottage - Private Pool & Near Duval
House
Key West, FL, 33040, United States
0.2k from Observation Tower center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
5.6

Review score

4 reviews

$1929
Average price / night
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The Rigby House - Pool, One block from Duval St
The Rigby House - Pool, One block from Duval St
House
Key West, FL, 33040, United States
0.2k from Observation Tower center

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

6 Bedrooms12 Guests
10.0

Exceptional

14 reviews

$3552
Average price / night
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Banana's Foster Guesthouse
Banana's Foster Guesthouse
House
537 Caroline St, Key West, FL, 33040, United States
0.2k from Observation Tower center

AC, Barbecue, Internet, Laundry, Microwave, No Smoking, Outdoor Grill, Outdoor Space, Pool

8.2

Very Good

16 reviews

$411
Average price / night
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Ann Street Gardens - Downtown Key West
Ann Street Gardens - Downtown Key West
Cottage
Key West, FL, 33040, United States
0.2k from Observation Tower center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$489
Average price / night
Check Availability
2 Sunset Harbor Resort, Pool, Hot Tub, In Town!
2 Sunset Harbor Resort, Pool, Hot Tub, In Town!
Resort
Key West, FL, 33040, United States
0.2k from Observation Tower center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms2 Guests
New to Booking
$2137
Average price / night
Check Availability
2 Sunset Harbor Resort Key West, Hot Tub, Pool!
2 Sunset Harbor Resort Key West, Hot Tub, Pool!
Resort
Key West, FL, 33040, United States
0.2k from Observation Tower center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
New to Booking
$2025
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 with Pool in Observation Tower.

Where to stay in Observation Tower? Best neighborhoods & areas

Observation Tower Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in Observation Tower. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Observation Tower vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $279 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Observation Tower offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Observation Tower welcome pets. Currently, 32 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Observation Tower often include additional outdoor features such as Pool, View, and Balcony/Terrace. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Observation Tower offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.