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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Midtown

Refine your search

Price per night

Amenity Filter

Rating

1736 Best Vacation 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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
**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
Check Availability
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
Check Availability
**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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
~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
Check Availability
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
Check Availability
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
Check Availability
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 Vacation Rentals in Midtown.

Where to stay in Midtown? Best neighborhoods & areas

Stay Near Midtown's Top Attractions

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

Midtown Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1736 verified vacation rentals in Midtown. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Midtown vary depending on the season, property size, and location. Rates typically start from around $247 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Midtown include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Midtown welcome pets. Currently, 28 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Midtown often include amenities such as Pool, Laundry, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.