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

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  1. VBOR
  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Downtown

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1053 Best Oceanfront Rentals in Downtown (Starting from $142)

Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.1k from Downtown 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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**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.0k from Downtown center

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

16 Bedrooms32 Guests
10.0

Exceptional

5 reviews

$4416
Average price / night
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New Orleans House - Gay Male Adult Guesthouse
New Orleans House - Gay Male Adult Guesthouse
House
Downtown, Key West, Florida, USA
0.1k from Downtown 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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**MAYA’S SECRET TREASURE @ DUVAL** Pool & Balcony over Duval + LAST KEY SERVICES
**MAYA’S SECRET TREASURE @ DUVAL** Pool & Balcony over Duval + LAST KEY SERVICES
Condo
Key West, FL, 33040, United States
0.0k from Downtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

91 reviews

$1744
Average price / night
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Courtney's Place Historic Cottages & Inns
Courtney's Place Historic Cottages & Inns
House
Downtown, Key West, Florida, USA
0.2k from Downtown 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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Sky Suite with Balcony Overlooking Duval Street
Sky Suite with Balcony Overlooking Duval Street
Apartment
Key West, FL, 33040, United States
0.0k from Downtown center

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

2 Bedrooms6 Guests
9.6

Exceptional

48 reviews

$929
Average price / night
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Tranquillity Guest House
Tranquillity Guest House
Apartment
Key West, FL, USA
0.3k from Downtown 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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Cloud Suite on Duval Street with Balcony
Cloud Suite on Duval Street with Balcony
Apartment
Key West, FL, 33040, United States
0.0k from Downtown center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$908
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
0.3k from Downtown 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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Sky Suites Retreat - Balcony Overlooking Duval
Sky Suites Retreat - Balcony Overlooking Duval
Apartment
Key West, FL, 33040, United States
0.0k from Downtown center

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

4 Bedrooms12 Guests
10.0

Exceptional

18 reviews

$1911
Average price / night
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Caribbean House
Caribbean House
House
Key West, FL, USA
0.3k from Downtown center

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

11 Bedrooms20 Guests
8.8

Fabulous

457 reviews

$735
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
0.1k from Downtown 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 - Main House
Bahama Gardens - Main House
House
Key West, FL, USA
0.3k from Downtown 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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Shipwreck Suite - Apartment on Duval St, Key West!
Shipwreck Suite - Apartment on Duval St, Key West!
Apartment
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Balcony, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool, TV

1 Bedroom6 Guests
10.0

Exceptional

2 reviews

$142
Average price / night
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Bahama Gardens - Cigar House
Bahama Gardens - Cigar House
House
Key West, FL, USA
0.3k from Downtown 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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Casa Mamisa - 2 bedroom home in Old Town
Casa Mamisa - 2 bedroom home in Old Town
House
Key West, FL, 33040, United States
0.1k from Downtown 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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Bahama Gardens - Conch House
Bahama Gardens - Conch House
House
Key West, FL, USA
0.3k from Downtown 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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**BLUE HERON'S HIDEOUT @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVI
**BLUE HERON'S HIDEOUT @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVI
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

4 Bedrooms8 Guests
New to Booking
$487
Average price / night
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Bahama Gardens - Turtle House
Bahama Gardens - Turtle House
House
Key West, FL, USA
0.3k from Downtown 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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Contra House Key West
Contra House Key West
House
720 Simonton St, Key West, FL, 33040, United States
0.1k from Downtown center

AC, Barbecue, Free Parking, Internet, Laundry, No Smoking, Outdoor Grill, Outdoor Space, Pool

New to Booking
$1811
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 Downtown 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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**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

5 Bedrooms13 Guests
10.0

Exceptional

34 reviews

$1425
Average price / night
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**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
Condo
Key West, FL, 33040, United States
0.1k from Downtown center

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

3 Bedrooms6 Guests
9.8

Exceptional

128 reviews

$741
Average price / night
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**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

5 Bedrooms10 Guests
10.0

Exceptional

152 reviews

$1564
Average price / night
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**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
Condo
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

4 Bedrooms7 Guests
9.8

Exceptional

90 reviews

$833
Average price / night
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**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

6 Bedrooms12 Guests
9.8

Exceptional

95 reviews

$1921
Average price / night
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**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

5 Bedrooms10 Guests
9.8

Exceptional

83 reviews

$1388
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 Downtown.

Where to stay in Downtown? Best neighborhoods & areas

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VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Downtown Oceanfront Rentals on the Map

Frequently Asked Questions

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

Oceanfront rental prices in Downtown vary depending on the property size, exact beachfront location, and season. Rates typically start from around $142 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 Downtown 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 Downtown welcome pets. Currently, 36 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 Downtown often include features designed for a comfortable coastal stay, such as Ocean View, 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.