Pet-Friendly Rentals in Jackson Square, FL: Compare 10+ Sites & Save

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777 Best Pet-Friendly Rentals in Jackson Square (Starting from $162)

Bahamian Bamboo by Last Key Realty
Bahamian Bamboo by Last Key Realty
House
Key West, FL, USA
0.2k from Jackson Square center

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

3 Bedrooms6 Guests
New to Booking
$3038
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
0.1k from Jackson Square 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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Villa Angelita by Last Key Realty
Villa Angelita by Last Key Realty
House
Key West, FL, USA
0.2k from Jackson Square center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$1547
Average price / night
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**VOGUE VILLA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
**VOGUE VILLA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms7 Guests
New to Booking
$643
Average price / night
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Casita Angelita by Last Key Realty
Casita Angelita by Last Key Realty
House
Key West, FL, USA
0.2k from Jackson Square center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$329
Average price / night
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Sunset Overlook - Waterfront Condo at Harbour Place with Sunset View
Sunset Overlook - Waterfront Condo at Harbour Place with Sunset View
Condo
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Dryer, Elevator, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$325
Average price / night
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Sweet Home Angelita by Last Key Realty
Sweet Home Angelita by Last Key Realty
House
Key West, FL, USA
0.2k from Jackson Square center

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

5 Bedrooms13 Guests
New to Booking
$3351
Average price / night
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Casa Cristol- Family and Pet Friendly - Classic KW Charm Superb Location!
Casa Cristol- Family and Pet Friendly - Classic KW Charm Superb Location!
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

3 Bedrooms6 Guests
9.8

Exceptional

60 reviews

$1084
Average price / night
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Gulf Getaway
Gulf Getaway
House
Key West, FL, USA
0.2k from Jackson Square center

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

1 Bedroom6 Guests
New to Booking
$342
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
0.2k from Jackson Square 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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Americana Tropicale by Last Key Realty
Americana Tropicale by Last Key Realty
House
Key West, FL, USA
0.3k from Jackson Square center

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

4 Bedrooms10 Guests
New to Booking
$2020
Average price / night
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Casa Mamisa - 2 bedroom home in Old Town
Casa Mamisa - 2 bedroom home in Old Town
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms6 Guests
9.4

Superb

3 reviews

$162
Average price / night
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The Zesty Lime by Last Key Realty
The Zesty Lime by Last Key Realty
House
Key West, FL, USA
0.3k from Jackson Square center

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

1 Bedroom8 Guests
New to Booking
$1466
Average price / night
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**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

5 Bedrooms13 Guests
10.0

Exceptional

34 reviews

$1425
Average price / night
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The Toasted Coconut by Last Key Realty
The Toasted Coconut by Last Key Realty
House
Key West, FL, USA
0.3k from Jackson Square center

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

3 Bedrooms8 Guests
New to Booking
$1391
Average price / night
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**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
Condo
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.8

Exceptional

128 reviews

$741
Average price / night
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Good Vibrations by Last Key Realty
Good Vibrations by Last Key Realty
House
Key West, FL, USA
0.3k from Jackson Square center

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

4 Bedrooms10 Guests
New to Booking
$3011
Average price / night
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**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
Condo
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

4 Bedrooms7 Guests
9.8

Exceptional

90 reviews

$833
Average price / night
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The Royal Compound by Last Key Realty
The Royal Compound by Last Key Realty
House
Key West, FL, USA
0.3k from Jackson Square center

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

4 Bedrooms8 Guests
New to Booking
$10718
Average price / night
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THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms6 Guests
7.0

Good

4 reviews

$323
Average price / night
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Peak Of Duval
Peak Of Duval
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Balcony, Dryer, Extra Bed, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$386
Average price / night
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JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
Condo
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms4 Guests
9.6

Exceptional

181 reviews

$526
Average price / night
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Gulf Getaway | Condo w/Pool!
Gulf Getaway | Condo w/Pool!
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.8

Exceptional

9 reviews

$219
Average price / night
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BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.8

Exceptional

104 reviews

$1422
Average price / night
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**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR/2BA Cottage + LAST KEY SERVICES
**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR/2BA Cottage + LAST KEY SERVICES
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$306
Average price / night
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Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$215
Average price / night
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THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!
THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!
Condo
Key West, FL, 33040, United States
0.3k from Jackson Square center

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

2 Bedrooms4 Guests
10.0

Exceptional

27 reviews

$199
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 Pet-Friendly Rentals in Jackson Square.

Where to stay in Jackson Square? Best neighborhoods & areas

Jackson Square Pet-Friendly Rentals on the Map

Frequently Asked Questions

You can explore 777 verified pet-friendly rentals in Jackson Square. These include a range of homes, cabins, and condos that welcome pets, making it easier to plan a trip with your companion.

Pet fees in Jackson Square vary by property and may include a nightly charge or a one-time fee. Rates for pet-friendly rentals typically start from around $162 per night, with additional fees depending on the host’s policy.

Some pet-friendly rentals in Jackson Square may have weight or breed restrictions, while others are more flexible. It’s recommended to review the property’s house rules or contact the host to confirm whether your pet is allowed.

Some pet-friendly rentals in Jackson Square include fenced or partially enclosed outdoor spaces, which can be helpful for pets. Checking the listing details can help you find properties that offer secure outdoor areas.

Pet-friendly properties can be in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. Availability may be more flexible during off-peak periods.

Pet-friendly rentals in Jackson Square may include amenities such as Pet Friendly, Wellness Facilities, and Internet. These features help make stays more comfortable for both pets and their owners.

You can use map-based search features to find rentals located near dog parks, walking trails, or pet-friendly outdoor areas. This can help you choose a location that is convenient for daily walks and outdoor activities with your pet.