Beach Home Rentals in Jackson Square, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida

  5.  Key West
  6.  Jackson Square

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1006 Beach Home Rentals in Jackson Square (Starting from $162)

La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Resort
Key West, FL, USA
0.2k from Jackson Square 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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Lavender Jungle | Great Location w/ Patio & Shared Pool | Month-Long Stays
Lavender Jungle | Great Location w/ Patio & Shared Pool | Month-Long Stays
House
Key West, FL, 33040, United States
0.0k from Jackson Square center

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

2 Bedrooms4 Guests
8.8

Fabulous

15 reviews

$329
Average price / night
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Tranquillity Guest House
Tranquillity Guest House
Apartment
Key West, FL, USA
0.3k from Jackson Square 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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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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Garden of Emma by Last Key Realty
Garden of Emma by Last Key Realty
House
Key West, FL, USA
0.3k from Jackson Square 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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**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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Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.3k from Jackson Square 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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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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Bahama Gardens - Main House
Bahama Gardens - Main House
House
Key West, FL, USA
0.3k from Jackson Square 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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Southard Getaway | Covered Patio, Great Location, Shared Pool | Month Long Stays
Southard Getaway | Covered Patio, Great Location, Shared Pool | Month Long Stays
House
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Dryer, Extra Bed, Internet, Kitchen, Laundry, No Smoking, Patio, Pool

2 Bedrooms5 Guests
9.4

Superb

13 reviews

$396
Average price / night
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Bahama Gardens - Cigar House
Bahama Gardens - Cigar House
House
Key West, FL, USA
0.3k from Jackson Square 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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A Siesta Bay | Walk to Key West, Gated Community, Shared Pool | Month-Long Stays
A Siesta Bay | Walk to Key West, Gated Community, Shared Pool | Month-Long Stays
House
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, No Smoking, Patio

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$410
Average price / night
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Bahama Gardens - Conch House
Bahama Gardens - Conch House
House
Key West, FL, USA
0.3k from Jackson Square center

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

2 Bedrooms5 Guests
8.2

Very Good

5 reviews

$1058
Average price / night
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KAMP - Rooftop Penthouse Overlooking Duval
KAMP - Rooftop Penthouse Overlooking Duval
Apartment
Key West, FL, 33040, United States
0.1k from Jackson Square center

AC, Arcade, Balcony, Dryer, Elevator, Extra Bed, Heater, Internet, Kitchen

2 Bedrooms6 Guests
8.4

Very Good

21 reviews

$1190
Average price / night
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Bahama Gardens - Turtle House
Bahama Gardens - Turtle House
House
Key West, FL, USA
0.3k from Jackson Square center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$1326
Average price / night
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The Perch on Duval- Hip & Modern Duval Suite
The Perch on Duval- Hip & Modern Duval Suite
Apartment
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms5 Guests
9.8

Exceptional

15 reviews

$772
Average price / night
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Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 23
Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 23
House
Key West, FL, USA
0.3k from Jackson Square center

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

8 Bedrooms23 Guests
New to Booking
$4655
Average price / night
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PARADISE ON PORTER in the Truman Annex
PARADISE ON PORTER in the Truman Annex
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Dryer, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Patio, TV

2 Bedrooms4 Guests
10.0

Exceptional

53 reviews

$305
Average price / night
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New Orleans House - Gay Male Adult Guesthouse
New Orleans House - Gay Male Adult Guesthouse
House
Jackson Square, Key West, Florida, USA
0.3k from Jackson Square center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Hot tubs

13 Bedrooms28 Guests
8.8

Fabulous

193 reviews

$575
Average price / night
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A Caribbean Alternative townhome in Truman Annex
A Caribbean Alternative townhome in Truman Annex
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
9.4

Superb

25 reviews

$481
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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The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Complex
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Complex
Condo
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$574
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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Southard Quarter at Truman Annex | Walk to Duval
Southard Quarter at Truman Annex | Walk to Duval
Apartment
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

1 Bedroom3 Guests
New to Booking
$368
Average price / night
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OCEAN BREEZE BUNGALOW-Stunning 2 Bedroom / 2.5 Bathroom in Truman Annex
OCEAN BREEZE BUNGALOW-Stunning 2 Bedroom / 2.5 Bathroom in Truman Annex
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms4 Guests
New to Booking
$385
Average price / night
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Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

4 Bedrooms7 Guests
New to Booking
$837
Average price / night
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**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

53 reviews

$306
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 Beach Rentals in Jackson Square.

Where to stay in Jackson Square? Best neighborhoods & areas

Jackson Square Beach Rentals on the Map

Frequently Asked Questions

You can explore 1006 verified beach rentals in Jackson Square. 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 Jackson Square vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $162 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 Jackson Square 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 Jackson Square welcome pets. Currently, 21 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 Jackson Square often include amenities designed for coastal living, such as View, Ocean View, and Wellness Facilities. 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.