Short-Term Rentals in Midtown, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Key West
  6.  Midtown

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2250 Best Short-Term Rentals in Midtown (Starting from $247)

Flagler Station
Flagler Station
House
Key West, FL, USA
0.3k from Midtown center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

3 Bedrooms6 Guests
New to Booking
$408
Average price / night
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In the heart of Midtown
In the heart of Midtown
House
Key West, FL, 33040, United States
0.0k from Midtown center

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

2 Bedrooms4 Guests
New to Booking
$403
Average price / night
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Plantation Tropicale by Last Key Realty
Plantation Tropicale by Last Key Realty
House
Key West, FL, USA
0.4k from Midtown center

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

5 Bedrooms12 Guests
New to Booking
$2964
Average price / night
Check Availability
**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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Casa de Sunshine
Casa de Sunshine
House
Key West, FL, USA
0.5k from Midtown center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$358
Average price / night
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Island Time on Washington : Stylish 4BR Key West Home, Heated Pool, Dogs OK, Parking & Near Beaches
Island Time on Washington : Stylish 4BR Key West Home, Heated Pool, Dogs OK, Parking & Near Beaches
House
Key West, FL, 33040, United States
0.1k from Midtown center

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

4 Bedrooms10 Guests
New to Booking
$312
Average price / night
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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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**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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Sunshine Drive
Sunshine Drive
House
Key West, FL, USA
0.5k from Midtown center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals

3 Bedrooms10 Guests
New to Booking
$391
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 Hidden Oasis- Waterfall Pool Close to Beach
New Hidden Oasis- Waterfall Pool Close to Beach
House
Key West, FL, USA
0.5k from Midtown center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms6 Guests
New to Booking
$526
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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Sundial on the Atlantic Ocean View
Sundial on the Atlantic Ocean View
House
FL, USA
0.6k from Midtown center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$870
Average price / night
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Tranquil Beauty-Private Pool - Outside Lanai-Beaches Nearby
Tranquil Beauty-Private Pool - Outside Lanai-Beaches Nearby
House
Key West, FL, 33040, United States
0.1k from Midtown center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$247
Average price / night
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Ocean View
Ocean View
House
Key West, FL, USA
0.6k from Midtown center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$901
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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Banyan Suite
Banyan Suite
Apartment
Key West, FL, USA
0.6k from Midtown center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$337
Average price / night
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Nate's Place in Key West
Nate's Place in Key West
House
Key West, FL, 33040, United States
0.2k from Midtown center

AC, Dryer, Kitchen, Laundry, No Smoking, Outdoor Space, TV

3 Bedrooms5 Guests
New to Booking
$283
Average price / night
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Palm Suite
Palm Suite
Apartment
Key West, FL, USA
0.6k from Midtown center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$316
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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Island living 3-bed oasis w large pool, lush deck, cabana, outdoor shower
Island living 3-bed oasis w large pool, lush deck, cabana, outdoor shower
House
Key West, FL, 33040, United States
0.2k from Midtown center

AC, Dryer, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$612
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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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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
Luxurious monthly rental in mid-town
Luxurious monthly rental in mid-town
House
Key West, FL, 33040, United States
0.2k from Midtown center

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

3 Bedrooms6 Guests
9.6

Exceptional

8 reviews

$357
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 Short-Term Rentals in Midtown.

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Midtown Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 2250 verified short-term rentals in Midtown, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Midtown vary depending on location, property size, and travel dates. Rates typically start from around $247 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Midtown include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Midtown, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Midtown often include amenities such as Pool, Laundry, and Wellness Facilities, providing a comfortable and convenient stay.

Short-term rentals in Midtown are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.