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

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  2. Oceanfront Rentals
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  4.  Florida
  5.  Key West
  6.  Jackson Square

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1053 Best Oceanfront 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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**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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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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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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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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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 - 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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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 - 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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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 - 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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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 - 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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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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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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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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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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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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**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
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Sailor's Story at The Truman Annex in Key West
Sailor's Story at The Truman Annex in Key West
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms6 Guests
9.2

Superb

51 reviews

$324
Average price / night
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Sago Palm at The Truman Annex in Key West
Sago Palm at The Truman Annex in Key West
House
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

39 reviews

$323
Average price / night
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Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
Condo
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms4 Guests
10.0

Exceptional

232 reviews

$250
Average price / night
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STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
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
10.0

Exceptional

162 reviews

$438
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 Jackson Square.

Where to stay in Jackson Square? Best neighborhoods & areas

Jackson Square Oceanfront Rentals on the Map

Frequently Asked Questions

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

Oceanfront rental prices in Jackson Square vary depending on the property size, exact beachfront location, and season. Rates typically start from around $162 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 Jackson Square 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 Jackson Square welcome pets. Currently, 21 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 Jackson Square 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.