Oceanfront Rentals in Uptown - Upper Duval, FL: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Uptown - Upper Duval

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1053 Best Oceanfront Rentals in Uptown - Upper Duval (Starting from $225)

H2O Suites- Adults Only
H2O Suites- Adults Only
Resort
Uptown - Upper Duval, Key West, Florida, USA
0.1k from Uptown - Upper Duval 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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Hidden away near the Southernmost Point, Louisa's Hideaway is it!
Hidden away near the Southernmost Point, Louisa's Hideaway is it!
House
Key West, FL, 33040, United States
0.0k from Uptown - Upper Duval center

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

3 Bedrooms6 Guests
10.0

Exceptional

200 reviews

$1376
Average price / night
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Santa Maria Suites Resort
Santa Maria Suites Resort
Resort
Key West, FL, USA
0.2k from Uptown - Upper Duval 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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LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
House
Key West, FL, 33040, United States
0.0k from Uptown - Upper Duval center

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

3 Bedrooms8 Guests
9.8

Exceptional

239 reviews

$1282
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
0.3k from Uptown - Upper Duval 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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ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 block to Duval!
ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 block to Duval!
House
Key West, FL, 33040, United States
0.0k from Uptown - Upper Duval center

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

2 Bedrooms6 Guests
9.8

Exceptional

160 reviews

$796
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
0.4k from Uptown - Upper Duval 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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Keys Breeze - Walk to Duval, Private Pool
Keys Breeze - Walk to Duval, Private Pool
House
Key West, FL, 33040, United States
0.0k from Uptown - Upper Duval center

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

3 Bedrooms6 Guests
10.0

Exceptional

27 reviews

$1737
Average price / night
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Elizabeth's Secret - Old Town Key West
Elizabeth's Secret - Old Town Key West
House
Key West, FL, USA
0.5k from Uptown - Upper Duval 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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**A ROYAL AFFAIR @ DUVAL** Three Home Compound + LAST KEY SERVICES…
**A ROYAL AFFAIR @ DUVAL** Three Home Compound + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

14 Bedrooms34 Guests
10.0

Exceptional

1 reviews

$4014
Average price / night
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Courtney's Place Historic Cottages & Inns
Courtney's Place Historic Cottages & Inns
House
Uptown - Upper Duval, Key West, Florida, USA
0.6k from Uptown - Upper Duval 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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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
0.1k from Uptown - Upper Duval 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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New Orleans House - Gay Male Adult Guesthouse
New Orleans House - Gay Male Adult Guesthouse
House
Uptown - Upper Duval, Key West, Florida, USA
0.6k from Uptown - Upper Duval 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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Garden of Roses | Private Hot Tub, Prime Key West Location!
Garden of Roses | Private Hot Tub, Prime Key West Location!
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
New to Booking
$257
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
0.7k from Uptown - Upper Duval 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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Sea Esta Suite | Located On Iconic Duval w/ Pool
Sea Esta Suite | Located On Iconic Duval w/ Pool
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

2 Bedrooms6 Guests
9.8

Exceptional

41 reviews

$1002
Average price / night
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Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
0.7k from Uptown - Upper Duval center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 5-star, Lodgings

27 Bedrooms76 Guests
7.6

Good

261 reviews

$416
Average price / night
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**DOS CASITAS @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
**DOS CASITAS @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

2 Bedrooms14 Guests
New to Booking
$2219
Average price / night
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Caribbean House
Caribbean House
House
Key West, FL, USA
0.7k from Uptown - Upper Duval 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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Casa Havana | Old Town Condo w/ Pool & Balcony
Casa Havana | Old Town Condo w/ Pool & Balcony
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

2 Bedrooms4 Guests
7.0

Good

2 reviews

$875
Average price / night
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**HALFWAY TO HAVANA @ DUVAL** Two Cottages w/ Pool + LAST KEY SERVICES...
**HALFWAY TO HAVANA @ DUVAL** Two Cottages w/ Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

4 Bedrooms8 Guests
New to Booking
$1523
Average price / night
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**PALMS ON DUVAL @ OLD TOWN** Private Home w/ Pool + LAST KEY SERVICES...
**PALMS ON DUVAL @ OLD TOWN** Private Home w/ Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1471
Average price / night
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Pete's West Cottage steps from Duval
Pete's West Cottage steps from Duval
Cottage
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

AC, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.6

Exceptional

101 reviews

$580
Average price / night
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**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

7 Bedrooms16 Guests
10.0

Exceptional

89 reviews

$2676
Average price / night
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**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

5 Bedrooms12 Guests
10.0

Exceptional

49 reviews

$2304
Average price / night
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Louisa House: A comfortable four bedroom vacation hideaway
Louisa House: A comfortable four bedroom vacation hideaway
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

4 Bedrooms10 Guests
9.4

Superb

177 reviews

$1464
Average price / night
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Catherine House: A charming Old Town Key West cottage
Catherine House: A charming Old Town Key West cottage
House
Key West, FL, 33040, United States
0.1k from Uptown - Upper Duval center

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

2 Bedrooms4 Guests
9.8

Exceptional

191 reviews

$816
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 Uptown - Upper Duval.

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Uptown - Upper Duval Oceanfront Rentals on the Map

Frequently Asked Questions

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

Oceanfront rental prices in Uptown - Upper Duval vary depending on the property size, exact beachfront location, and season. Rates typically start from around $225 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 Uptown - Upper Duval 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 Uptown - Upper Duval welcome pets. Currently, 42 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 Uptown - Upper Duval often include features designed for a comfortable coastal stay, such as View, Oceanfront, 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.