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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Midtown

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485 Best Vacation Rentals with Private Pool in Midtown (Starting from $143)

Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
House
Midtown, Key West, Florida, USA
1.5k from Midtown center

Pool, Private Pool, Kitchen, Parking, Internet, Air Conditioner, Child Friendly

1 Bedroom4 Guests
New to Booking
$348
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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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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**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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**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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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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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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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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~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 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
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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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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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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
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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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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
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South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub
South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub
House
Key West, FL, 33040, United States
0.3k from Midtown center

AC, Barbecue, Dryer, Hot Tub, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

30 reviews

$266
Average price / night
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**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach
**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

2 Bedrooms8 Guests
10.0

Exceptional

19 reviews

$143
Average price / night
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Gorgeous beach bungalow just steps from the beach!
Gorgeous beach bungalow just steps from the beach!
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$223
Average price / night
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The Secret Grotto
The Secret Grotto
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

4 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$611
Average price / night
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**THE ENCHANTED ROSE @ BEACHSIDE** Gorgeous Home & Pool + LAST KEY SERVICES…
**THE ENCHANTED ROSE @ BEACHSIDE** Gorgeous 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 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$466
Average price / night
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Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!
Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!
House
Key West, FL, 33040, United States
0.3k from Midtown center

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

3 Bedrooms6 Guests
New to Booking
$260
Average price / night
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Tropical 3BR Casa Marina Retreat w/ Private Pool — Steps to Higgs Beach
Tropical 3BR Casa Marina Retreat w/ Private Pool — Steps to Higgs Beach
House
Key West, FL, 33040, United States
0.4k from Midtown center

AC, Barbecue, Dryer, Kitchen, Microwave, No Smoking, Pool, TV, Washer

3 Bedrooms8 Guests
New to Booking
$251
Average price / night
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A Bella Capri in Key West by the Beach!
A Bella Capri in Key West by the Beach!
House
Key West, FL, 33040, United States
0.4k from Midtown center

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

5 Bedrooms10 Guests
9.4

Superb

6 reviews

$612
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 Vacation Rentals with Private Pool in Midtown.

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Midtown Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 485 verified vacation rentals with a private pool in Midtown. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Midtown vary depending on the property size, location, and travel season. Rates typically start from around $143 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Midtown also welcome pets. Currently, 31 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Midtown often include additional features such as Pool, Private Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Midtown include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.