Jackson Square Vacation Rentals & Ski-in/Ski-out Homes

Compare Vacation Rentals & Ski-in/Ski-out Homes in Jackson Square, Key West, Florida, USA

New Casa Bonita Key West ~ by Rent Key West Vacations
Condo
Casa Bonita Key West ~ by Rent Key West Vacations
From US $1,278 per night
New
2 Bedrooms 6 Guests
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Mar Y Sol Ocean Front
House
Mar Y Sol Ocean Front
From US $887 per night
|
10.0 (4 Reviews)
3 Bedrooms 8 Guests
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Latitude Penthouse Key West
Apartment
Latitude Penthouse Key West
From US $671 per night
|
10.0 (4 Reviews)
2 Bedrooms 6 Guests
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Somewhere on the beach
House
Somewhere on the beach
From US $695 per night
|
10.0 (3 Reviews)
2 Bedrooms 6 Guests
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Sunnyside Up by Brightwild Pool Parking
Apartment
Sunnyside Up by Brightwild Pool Parking
From US $958 per night
|
10.0 (1 Review)
1 Bedroom 2 Guests
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The Perch on Duval
Apartment
The Perch on Duval
From US $575 per night
|
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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Yellowfin Ledge
House
Yellowfin Ledge
From US $364 per night
10.0 (3 Reviews)
1 Bedroom 3 Guests
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Two Duval Street Suites w parking and pool
House
Two Duval Street Suites w parking and pool
From US $1,658 per night
|
10.0 (2 Reviews)
2 Bedrooms 8 Guests
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Duval Hideaway
House
Duval Hideaway
From US $830 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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6 Bedroom 6 Bath Guesthouse on Duval Street
House
6 Bedroom 6 Bath Guesthouse on Duval Street
From US $6,002 per night
|
10.0 (1 Review)
6 Bedrooms 24 Guests
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New The Conch Republic Cooler
House
The Conch Republic Cooler
From US $343 per night
New
3 Bedrooms 6 Guests
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Bahama Gardens - Main House
House
Bahama Gardens - Main House
From US $2,211 per night
|
10.0 (1 Review)
4 Bedrooms 8 Guests
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Duke of Catherine by Last Key Realty
House
Duke of Catherine by Last Key Realty
From US $1,747 per night
|
10.0 (1 Review)
2 Bedrooms 8 Guests
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Villa Angelita by Last Key Realty
House
Villa Angelita by Last Key Realty
From US $1,547 per night
|
10.0 (1 Review)
3 Bedrooms 7 Guests
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Natures Edge by Last Key Realty
Apartment
Natures Edge by Last Key Realty
From US $1,007 per night
|
10.0 (1 Review)
2 Bedrooms 6 Guests
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Blue Moonshine on the Atlantic
House
Blue Moonshine on the Atlantic
From US $981 per night
|
10.0 (1 Review)
2 Bedrooms 6 Guests
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Anchor Drop Key West
House
Anchor Drop Key West
From US $969 per night
|
10.0 (1 Review)
2 Bedrooms 6 Guests
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Atlantic Sunrise Penthouse
House
Atlantic Sunrise Penthouse
From US $878 per night
|
10.0 (1 Review)
3 Bedrooms 8 Guests
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Casa Serendipity by Last Key Realty
House
Casa Serendipity by Last Key Realty
From US $809 per night
|
10.0 (1 Review)
3 Bedrooms 6 Guests
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PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
Cottage
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
From US $1,338 per night
10.0 (221 Reviews)
2 Bedrooms 4 Guests
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MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Condo
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
From US $435 per night
10.0 (187 Reviews)
2 Bedrooms 5 Guests
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Absolutely Paradise
House
Absolutely Paradise
From US $733 per night
|
10.0 (1 Review)
3 Bedrooms 8 Guests
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Road s End by Brightwild Steps to Duval St
Apartment
Road s End by Brightwild Steps to Duval St
From US $849 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Half block to Duval @ Mango Hideaway -studio apt
Apartment
Half block to Duval @ Mango Hideaway -studio apt
From US $525 per night
10.0 (91 Reviews)
1 Bedroom 3 Guests
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Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom
House
Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom
From US $660 per night
|
10.0 (1 Review)
1 Bedroom 8 Guests
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Duval Dream Loft by Brightwild Right on Duval
Apartment
Duval Dream Loft by Brightwild Right on Duval
From US $744 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Oceanfront Oasis
House
Oceanfront Oasis
From US $620 per night
|
10.0 (1 Review)
2 Bedrooms 6 Guests
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Artist House Key West
Bed & Breakfast
Artist House Key West
From US $148 per night
|
9.8 (414 Reviews)
1 Bedroom 2 Guests
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Conch in the Treetops by Last Key Realty
House
Conch in the Treetops by Last Key Realty
From US $402 per night
|
10.0 (1 Review)
2 Bedrooms 6 Guests
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"Tranquility " At Ann Street Gardens Steps From Duval
Cottage
"Tranquility " At Ann Street Gardens Steps From Duval
From US $602 per night
10.0 (78 Reviews)
1 Bedroom 2 Guests
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Old Town Garden Villas - Abaco Suite
Apartment
Old Town Garden Villas - Abaco Suite
From US $367 per night
|
10.0 (1 Review)
1 Bedroom 4 Guests
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Casita Angelita by Last Key Realty
House
Casita Angelita by Last Key Realty
From US $329 per night
|
10.0 (1 Review)
2 Bedrooms 6 Guests
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Four Flowers Guesthouse
Apartment
Four Flowers Guesthouse
From US $875 per night
|
10.0 (1 Review)
4 Bedrooms 14 Guests
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Duval Street Suite w kitchen and shared heated pool
Apartment
Duval Street Suite w kitchen and shared heated pool
From US $609 per night
|
10.0 (1 Review)
1 Bedroom 4 Guests
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Suzys Parrot Perch by Last Key Realty
Apartment
Suzys Parrot Perch by Last Key Realty
From US $586 per night
|
10.0 (1 Review)
2 Bedrooms 6 Guests
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PARROTVILLE Townhome in Windward Park by RENT KEY WEST VACATIONS
House
PARROTVILLE Townhome in Windward Park by RENT KEY WEST VACATIONS
From US $650 per night
10.0 (61 Reviews)
2 Bedrooms 4 Guests
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American Shoal Light Suite
House
American Shoal Light Suite
From US $512 per night
|
10.0 (1 Review)
1 Bedroom 6 Guests
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About Jackson Square Vacation Rentals

Explore over 3535 vacation rentals in Jackson Square with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Jackson Square for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Jackson Square. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Jackson Square tailored to your preferences. On average, these rentals offer 783.55 ft² of space, and are priced at an average of US $734 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Jackson Square at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Frequently Asked Questions About Jackson Square?

What are the top vacation rentals in Jackson Square?

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Discover the ideal vacation rental in Jackson Square with SunSki Resorts™. We provide an extensive selection of over 3535 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Jackson Square.

Nearby Neighborhood (12)

Neighborhood Property Count
Key West Historic District Vacation Rentals in Key West, Florida 637
Old Town Vacation Rentals in Key West, Florida 592
Downtown Vacation Rentals in Key West, Florida 285
Uptown - Upper Duval Vacation Rentals in Key West, Florida 199
Historic Seaport Vacation Rentals in Key West, Florida 113
Truman Annex Vacation Rentals in Key West, Florida 68
Meadows Vacation Rentals in Key West, Florida 29
Bahama Village Vacation Rentals in Key West, Florida 339
New Town Vacation Rentals in Key West, Florida 415
Midtown Vacation Rentals in Key West, Florida 407
Geiger Key Vacation Rentals in Key West, Florida 35
Sunset Key Vacation Rentals in Key West, Florida 3214

There are 3535 Jackson Square, FL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Jackson Square