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

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  1. VBOR
  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Midtown

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1053 Best Oceanfront Rentals in Midtown (Starting from $205)

Belle of the Beach by Last Key Realty
Belle of the Beach by Last Key Realty
House
Key West, FL, USA
0.5k from Midtown center

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

6 Bedrooms16 Guests
New to Booking
$2390
Average price / night
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**73 PALMS @ MIDTOWN** Renovated Home & Pool + LAST KEY SERVICES…
**73 PALMS @ MIDTOWN** Renovated Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.1k from Midtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$379
Average price / night
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Atlantic Reflections by Last Key Realty
Atlantic Reflections by Last Key Realty
Apartment
Key West, FL, USA
0.6k from Midtown center

Apartments, Accommodations, Parking, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$1286
Average price / night
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**CASA DEL MONO @ MIDTOWN** Stunning Private Home & Pool + LAST KEY SERVICES…
**CASA DEL MONO @ MIDTOWN** Stunning Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.1k from Midtown center

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

5 Bedrooms10 Guests
New to Booking
$640
Average price / night
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Conch in the Treetops by Last Key Realty
Conch in the Treetops by Last Key Realty
House
Key West, FL, USA
0.6k from Midtown center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$402
Average price / night
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**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.1k from Midtown center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$521
Average price / night
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NEW Atlantic Escape - Beach & Pool
NEW Atlantic Escape - Beach & Pool
Apartment
Key West, FL, USA
0.7k from Midtown center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$205
Average price / night
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BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
House
Key West, FL, 33040, United States
0.1k from Midtown center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$470
Average price / night
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Suite Sanctuary by Last Key Realty
Suite Sanctuary by Last Key Realty
Apartment
Key West, FL, USA
0.7k from Midtown center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1003
Average price / night
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WALKING ON SUNSHINE ~ Exquisite 3 BR, 3 Ba Home w/ Heated Pool & Parking!
WALKING ON SUNSHINE ~ Exquisite 3 BR, 3 Ba Home w/ Heated Pool & Parking!
House
Key West, FL, 33040, United States
0.1k from Midtown center

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

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$384
Average price / night
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Windswept Palms by Last Key Realty
Windswept Palms by Last Key Realty
Apartment
Key West, FL, USA
0.7k from Midtown center

Apartments, Accommodations, Parking, Lodgings, Jacuzzis, Places to stay

3 Bedrooms6 Guests
New to Booking
$585
Average price / night
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~BLUE HAVEN~ Welcome to this single-story retreat with a pool!
~BLUE HAVEN~ Welcome to this single-story retreat with a pool!
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

4 Bedrooms8 Guests
New to Booking
$844
Average price / night
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Walking on Sunshine by Last Key Realty
Walking on Sunshine by Last Key Realty
Apartment
Key West, FL, USA
0.7k from Midtown center

Apartments, Accommodations, Parking, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$882
Average price / night
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ISLAND SANCTUARY KEY WEST - 3 Bedroom / 2 Bathroom with Pool and Parking!
ISLAND SANCTUARY KEY WEST - 3 Bedroom / 2 Bathroom with Pool and Parking!
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

3 Bedrooms6 Guests
New to Booking
$327
Average price / night
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Follow The Sun by Last Key Realty
Follow The Sun by Last Key Realty
Apartment
Key West, FL, USA
0.7k from Midtown center

Apartments, Accommodations, Parking, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
6.0

Review score

1 reviews

$1021
Average price / night
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POOLSIDE PARADISE ~ Charming 3 BR/2Ba Home w/ Pool!
POOLSIDE PARADISE ~ Charming 3 BR/2Ba Home w/ Pool!
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

3 Bedrooms8 Guests
New to Booking
$407
Average price / night
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Natures Edge by Last Key Realty
Natures Edge by Last Key Realty
Apartment
Key West, FL, USA
0.7k from Midtown center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1007
Average price / night
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Casa del Sol
Casa del Sol
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

6 Bedrooms12 Guests
New to Booking
$337
Average price / night
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Neptunes Penthouse by Last Key Realty
Neptunes Penthouse by Last Key Realty
Apartment
Key West, FL, USA
0.7k from Midtown center

Apartments, Accommodations, Parking, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$438
Average price / night
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Island Time Escape - Charming Family Retreat
Island Time Escape - Charming Family Retreat
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

3 Bedrooms6 Guests
New to Booking
$376
Average price / night
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Villa Paradiso: A unique mid-town paradise
Villa Paradiso: A unique mid-town paradise
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

3 Bedrooms6 Guests
9.8

Exceptional

177 reviews

$1166
Average price / night
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SOUTHERNMOST SWIM AND SOCIAL CLUB
SOUTHERNMOST SWIM AND SOCIAL CLUB
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$720
Average price / night
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Perfect  2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$264
Average price / night
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BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/ Pool!
BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/ Pool!
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$490
Average price / night
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SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w/ Pool!
SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w/ Pool!
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$636
Average price / night
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**SUNFLOWER MELODIES @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
**SUNFLOWER MELODIES @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

3 Bedrooms6 Guests
New to Booking
$704
Average price / night
Check Availability
Turtle's Nest, 3 BR+3BA, dog friendly, Conch Cottage in Midtown Key West
Turtle's Nest, 3 BR+3BA, dog friendly, Conch Cottage in Midtown Key West
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

3 Bedrooms9 Guests
10.0

Exceptional

4 reviews

$370
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 Oceanfront Rentals in Midtown.

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Midtown Oceanfront Rentals on the Map

Frequently Asked Questions

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

Oceanfront rental prices in Midtown vary depending on the property size, exact beachfront location, and season. Rates typically start from around $205 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 Midtown 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 Midtown welcome pets. Currently, 35 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 Midtown often include features designed for a comfortable coastal stay, such as View, Oceanfront, and Wellness Facilities. 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.