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

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Old Town

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1053 Best Oceanfront 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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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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**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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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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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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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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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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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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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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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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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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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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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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The Pirates Penthouse by Last Key Realty
The Pirates Penthouse by Last Key Realty
Apartment
Key West, FL, USA
0.6k from Old Town center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
9.3

Superb

3 reviews

$964
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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The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
0.6k from Old Town center

Accommodations, Pools, Resorts, Parking, Spa, Pet-friendly, 4-star, Lodgings, Beach

130 Bedrooms42 Guests
7.6

Good

287 reviews

$418
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
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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
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Monkey House by AvantStay | Pool, by Duval Street
Monkey House by AvantStay | Pool, by Duval Street
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms4 Guests
New to Booking
$292
Average price / night
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STAR OF THE SEA ~ Renovated 2 BR, 2.5 Ba Townhome w/ Shared Pool!
STAR OF THE SEA ~ Renovated 2 BR, 2.5 Ba Townhome w/ Shared Pool!
House
Key West, FL, 33040, United States
0.2k from Old Town center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$246
Average price / night
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**TOP OF OLD TOWN @ DUVAL SQUARE** Renovated Home + LAST KEY SERVICES…
**TOP OF OLD TOWN @ DUVAL SQUARE** Renovated Home + LAST KEY SERVICES…
Condo
Key West, FL, 33040, United States
0.2k from Old Town center

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

2 Bedrooms6 Guests
10.0

Exceptional

18 reviews

$826
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 Old Town.

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Old Town Oceanfront Rentals on the Map

Frequently Asked Questions

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

Oceanfront rental prices in Old Town vary depending on the property size, exact beachfront location, and season. Rates typically start from around $120 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 Old Town 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 Old Town welcome pets. Currently, 31 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 Old Town often include features designed for a comfortable coastal stay, such as View, Ocean View, and Oceanfront. 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.