Beach Home Rentals in Old Town, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida

  5.  Key West
  6.  Old Town

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1022 Beach Home Rentals in Old Town (Starting from $120)

Elizabeth's Secret - Old Town Key West
Elizabeth's Secret - Old Town Key West
House
Key West, FL, USA
0.1k from Old Town center

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

3 Bedrooms6 Guests
New to Booking
$1628
Average price / night
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**WINDWARD WAVES @ OLD TOWN** Cozy Cottage Near Duval + LAST KEY SERVICES...
**WINDWARD WAVES @ OLD TOWN** Cozy Cottage Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

4 Bedrooms6 Guests
New to Booking
$668
Average price / night
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Old Town Garden Villas
Old Town Garden Villas
House
Old Town, Key West, Florida, USA
0.2k from Old Town center

View, Internet, Pool, Air Conditioner, Ocean View, Child Friendly

2 Bedrooms8 Guests
9.5

Superb

19 reviews

$258
Average price / night
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**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

2 Bedrooms4 Guests
9.8

Exceptional

79 reviews

$706
Average price / night
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H2O Suites- Adults Only
H2O Suites- Adults Only
Resort
Old Town, Key West, Florida, USA
0.3k from Old Town center

Luxury, Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay

22 Bedrooms6 Guests
9.5

Superb

508 reviews

$1688
Average price / night
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Breezy Retreat  2bdrm, 2 bath Windward Park,  Pool, close to Duval
Breezy Retreat 2bdrm, 2 bath Windward Park, Pool, close to Duval
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

2 Bedrooms4 Guests
9.8

Exceptional

20 reviews

$910
Average price / night
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Courtney's Place Historic Cottages & Inns
Courtney's Place Historic Cottages & Inns
House
Old Town, Key West, Florida, USA
0.3k from Old Town center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Romantic, Pet-friendly, Lodgings

18 Bedrooms72 Guests
8.8

Fabulous

1291 reviews

$738
Average price / night
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Location, location, location in the heart of Old Town!
Location, location, location in the heart of Old Town!
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$619
Average price / night
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Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.4k from Old Town 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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The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$366
Average price / night
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New Orleans House - Gay Male Adult Guesthouse
New Orleans House - Gay Male Adult Guesthouse
House
Old Town, Key West, Florida, USA
0.4k from Old Town 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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VanGogh Studio | Updated, Old Town, Heated Pool
VanGogh Studio | Updated, Old Town, Heated Pool
Apartment
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Grill

1 Bedroom2 Guests
8.6

Fabulous

41 reviews

$371
Average price / night
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Alexander Palms Court - No Hidden Resort Fees!
Alexander Palms Court - No Hidden Resort Fees!
House
Key West, FL, USA
0.5k from Old Town center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

12 Bedrooms35 Guests
8.6

Fabulous

894 reviews

$225
Average price / night
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DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

4 Bedrooms8 Guests
9.8

Exceptional

18 reviews

$1736
Average price / night
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Santa Maria Suites Resort
Santa Maria Suites Resort
Resort
Key West, FL, USA
0.5k from Old Town center

Accommodations, Pools, Resorts, Parking, Romantic, Boutique, 4-star, Lodgings, Places to stay

35 Bedrooms20 Guests
9.3

Superb

674 reviews

$432
Average price / night
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SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms6 Guests
10.0

Exceptional

20 reviews

$239
Average price / night
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Chic 2 Bedroom Condo 300 Steps from Duval St
Chic 2 Bedroom Condo 300 Steps from Duval St
Apartment
Key West, FL, USA
0.5k from Old Town center

Wheelchair Accessible, Ocean View, Pet Friendly, Parking, Air Conditioner, Smoking, View

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$276
Average price / night
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INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w/ Community Pool!
INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w/ Community Pool!
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$282
Average price / night
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Tranquillity Guest House
Tranquillity Guest House
Apartment
Key West, FL, USA
0.6k from Old Town 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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A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

3 Bedrooms8 Guests
9.8

Exceptional

103 reviews

$1134
Average price / night
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ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms6 Guests
9.8

Exceptional

91 reviews

$1156
Average price / night
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Duval Breeze by AvantStay | Great Location | Close to Beach & Nightlife!
Duval Breeze by AvantStay | Great Location | Close to Beach & Nightlife!
House
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Balcony, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, No Smoking

2 Bedrooms6 Guests
9.2

Superb

90 reviews

$941
Average price / night
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Sanctuary Adorable Gated Loft Studio Old Town Close to Duval - Location Location
Sanctuary Adorable Gated Loft Studio Old Town Close to Duval - Location Location
Apartment
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$120
Average price / night
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Casa Louisa - XMAS IN KW! 2 Bed in Old Town - Right off Duval/Great Front Porch
Casa Louisa - XMAS IN KW! 2 Bed in Old Town - Right off Duval/Great Front Porch
House
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$157
Average price / night
Check Availability
Duval Sq., Old Town, very walkable, full kitchen, pool, parking, 2 BR/2.5 BA.
Duval Sq., Old Town, very walkable, full kitchen, pool, parking, 2 BR/2.5 BA.
Condo
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$234
Average price / night
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ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

3 Bedrooms6 Guests
9.8

Exceptional

105 reviews

$1015
Average price / night
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Heated Rooftop Pool, Gated Parking - Casa Caribe
Heated Rooftop Pool, Gated Parking - Casa Caribe
Condo
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms6 Guests
8.6

Fabulous

23 reviews

$1086
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 Old Town.

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Frequently Asked Questions

You can explore 1022 verified beach rentals in Old Town. 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 Old Town vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $120 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 Old Town 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 Old Town welcome pets. Currently, 26 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 Old Town often include amenities designed for coastal living, such as View, Ocean View, and Laundry. 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.