Midtown pickleball Stays, Resort Rentals, & Homes
Condo
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
Hot Tub
Pool
Balcony/Terrace
Pet Friendly
US $460/Night
7 Nights - US $3,220
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
- Pool
View
Breakfast
Parking
US $953/Night
7 Nights - US $6,673
Cottage
- Key West
- ·
- Uptown - Upper Duval
- 0.15 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
Ocean View- Balcony/Terrace
- View
- Pet Friendly
US $563/Night
7 Nights - US $3,942
House
- Key West
- ·
- Key West Historic District
- 0.37 mi to center
9.8Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
960 ft²
Private Pool
Oceanfront
Fireplace/Heating- Pool
US $216/Night
7 Nights - US $1,513
House
- Key West
- ·
- Uptown - Upper Duval
- 0.06 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- Pet Friendly
Child Friendly
Security/Safety
US $364/Night
7 Nights - US $2,548
Condo
9.4Exceptional
(59 Reviews)
2 Bedrooms
3 Baths
6 Guests
1905 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $683/Night
7 Nights - US $4,782
Condo
9.4Exceptional
(56 Reviews)
2 Bedrooms
2 Baths
6 Guests
1186 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $578/Night
7 Nights - US $4,047
House
9.4Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $821/Night
7 Nights - US $5,749
Condo
9.4Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1099 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
US $554/Night
7 Nights - US $3,877
Luxury Places to Stay in Midtown
Over 4675+ Luxury Places to Stay in or Near Midtown
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
4 Baths
10 Guests
2400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,596/Night
7 Nights - US $11,175
House
9.6Exceptional
(28 Reviews)
3 Bedrooms
2 Baths
6 Guests
1938 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
US $1,002/Night
7 Nights - US $7,013
Condo
9.8Exceptional
(53 Reviews)
4 Bedrooms
3 Baths
8 Guests
2038 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $779/Night
7 Nights - US $5,452
Condo
9.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $768/Night
7 Nights - US $5,378
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
7 Guests
1650 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $739/Night
7 Nights - US $5,170
House
3 Bedrooms
3 Baths
6 Guests
1950 ft²
- Pool
- Balcony/Terrace
- Kitchen
Air Conditioner
US $616/Night
7 Nights - US $4,309
Condo
3 Bedrooms
4 Baths
8 Guests
1876 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $440/Night
7 Nights - US $3,080
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
1420 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $407/Night
7 Nights - US $2,846
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
1440 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $385/Night
7 Nights - US $2,698
Top-Rated Villas with a Pool in Midtown
Over 3447+ Top-Rated Private Villas with a Pool in or Near Midtown
House
2 Bedrooms
2 Baths
4 Guests
1092 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $366/Night
7 Nights - US $2,564
Hotel
10.0Exceptional
(1001 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $287/Night
7 Nights - US $2,008
Cottage
10.0Exceptional
(241 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $655/Night
7 Nights - US $4,588
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(218 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $403/Night
7 Nights - US $2,824
House
- Key West
- ·
- Truman Annex
- 0.17 mi to center
10.0Exceptional
(192 Reviews)
2 Bedrooms
2 Baths
4 Guests
1080 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $659/Night
7 Nights - US $4,611
Condo
- Key West
- ·
- Truman Annex
- 0.20 mi to center
10.0Exceptional
(192 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $326/Night
7 Nights - US $2,281
House
10.0Exceptional
(186 Reviews)
2 Bedrooms
2 Baths
6 Guests
765 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $661/Night
7 Nights - US $4,629
Villa
- Key West
- ·
- Key West Historic District
- 0.15 mi to center
10.0Exceptional
(185 Reviews)
3 Bedrooms
3 Baths
6 Guests
1628 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,425/Night
7 Nights - US $9,978
Condo
- Key West
- ·
- Bahama Village
- 0.14 mi to center
10.0Exceptional
(176 Reviews)
2 Bedrooms
1 Bath
4 Guests
680 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $395/Night
7 Nights - US $2,768
Pet-Friendly Villas in Midtown
Over 1392+ Pet-Friendly Private Villas in or Near Midtown
House
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $677/Night
7 Nights - US $4,742
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
645.83 ft²
- Fireplace/Heating
- Pool
- View
- Pet Friendly
US $1,339/Night
7 Nights - US $9,373
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
US $994/Night
7 Nights - US $6,955
New
House
3 Bedrooms
2 Baths
10 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $237/Night
7 Nights - US $1,660
House
- Key West
- ·
- Uptown - Upper Duval
- 0.10 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
785.77 ft²
- Pet Friendly
- Child Friendly
- Security/Safety
US $830/Night
7 Nights - US $5,809
House
2 Bedrooms
2 Baths
5 Guests
650 ft²
- Oceanfront
- Ocean View
- View
- Pet Friendly
US $218/Night
7 Nights - US $1,523
Apartment
10.0Exceptional
(97 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
Internet
US $373/Night
7 Nights - US $2,608
Condo
10.0Exceptional
(75 Reviews)
1 Bedroom
1 Bath
4 Guests
731 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $498/Night
7 Nights - US $3,486
Condo
- Key West
- ·
- Uptown - Upper Duval
- 0.12 mi to center
10.0Exceptional
(66 Reviews)
2 Bedrooms
1 Bath
10 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $536/Night
7 Nights - US $3,750
Large Private Villas in Midtown
Over 477+ Large Villas in or Near Midtown for Groups and Families
Villa
10.0Exceptional
(59 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $565/Night
7 Nights - US $3,956
House
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
4 Baths
12 Guests
2346.53 ft²
- Internet
- Child Friendly
Laundry- Security/Safety
US $2,693/Night
7 Nights - US $18,854
Villa
7.4Very Good
(3 Reviews)
1 Bedroom
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
US $421/Night
7 Nights - US $2,947
Villa
10.0Exceptional
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $316/Night
7 Nights - US $2,213
House
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
12 Guests
2443.41 ft²
- Fireplace/Heating
- Pool
- View
- Parking
US $2,823/Night
7 Nights - US $19,762
Villa
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $506/Night
7 Nights - US $3,541
Condo
- Key West
- ·
- Historic Seaport
- 0.17 mi to center
10.0Exceptional
(20 Reviews)
1 Bedroom
1 Bath
10 Guests
600 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $390/Night
7 Nights - US $2,728
House
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
10 Guests
850 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $704/Night
7 Nights - US $4,926
Villa
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $443/Night
7 Nights - US $3,098
Wheelchair Accessible Holiday Homes in Midtown
Over 1089+ Wheelchair Accessible Villas and Holiday Homes in or Near Midtown
Hotel
2 Baths
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,819/Night
7 Nights - US $12,734
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $474/Night
7 Nights - US $3,318
Bed & Breakfast
- Key West
- ·
- Bahama Village
- 0.09 mi to center
9.4Exceptional
(1005 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Parking
US $201/Night
7 Nights - US $1,410
Resort
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $801/Night
7 Nights - US $5,607
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Ocean View
- View
- Pet Friendly
- Parking
US $276/Night
7 Nights - US $1,932
Condo
10.0Exceptional
(167 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $311/Night
7 Nights - US $2,180
Condo
10.0Exceptional
(60 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Hot Tub
- Spa
- Pool
- Ocean View
US $790/Night
7 Nights - US $5,530
Condo
10.0Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $508/Night
7 Nights - US $3,556
Condo
10.0Exceptional
(26 Reviews)
3 Bedrooms
2 Baths
6 Guests
798 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $472/Night
7 Nights - US $3,301
Midtown Villas, Airbnb and Holiday Homes Under $200
Over 350+ Midtown Private Villas, Airbnb and Holiday Homes Under $200
House
- Key West
- ·
- Bahama Village
- 0.11 mi to center
10.0Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $190/Night
7 Nights - US $1,331
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
710.42 ft²
- Pool
- View
- Pet Friendly
- Parking
US $190/Night
7 Nights - US $1,330
Bed & Breakfast
- Key West
- ·
- Historic Seaport
- 0.16 mi to center
9.8Exceptional
(444 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
US $136/Night
7 Nights - US $951
Apartment
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
475 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $139/Night
7 Nights - US $970
Bed & Breakfast
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
9.0Exceptional
(1414 Reviews)
11 Bedrooms
7 Baths
18 Guests
235.27 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $199/Night
7 Nights - US $1,393
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
680 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $191/Night
7 Nights - US $1,336
Condo
- Key West
- ·
- Truman Annex
- 0.17 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
513 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $193/Night
7 Nights - US $1,348
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $183/Night
7 Nights - US $1,284
House
- Key West
- ·
- Key West Historic District
- 0.36 mi to center
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
2 Guests
540 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $170/Night
7 Nights - US $1,188
Instantly Bookable Villa Rentals in Midtown
Over 3039+ Instantly Bookable Private Villas in or Near Midtown
House
10.0Exceptional
(24 Reviews)
2 Bedrooms
2 Baths
4 Guests
1564 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $724/Night
7 Nights - US $5,068
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1266 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $261/Night
7 Nights - US $1,826
House
- Key West
- ·
- Historic Seaport
- 0.09 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $532/Night
7 Nights - US $3,726
Cottage
- Key West
- ·
- Historic Seaport
- 0.13 mi to center
9.4Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $640/Night
7 Nights - US $4,477
Apartment
- Key West
- ·
- Key West Historic District
- 0.15 mi to center
8.0Excellent
(18 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $321/Night
7 Nights - US $2,247
New
Hotel
10.0Exceptional
(2 Reviews)
3 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $1,099/Night
7 Nights - US $7,692
Hotel
10.0Exceptional
(2 Reviews)
3 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $802/Night
7 Nights - US $5,615
New
Hotel
10.0Exceptional
(2 Reviews)
2 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $571/Night
7 Nights - US $4,000
New
Hotel
10.0Exceptional
(1 Review)
6 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $2,199/Night
7 Nights - US $15,392
Book a Last Minute Place to Stay in Midtown
About Midtown Vacation Rentals
Discover over 4684 amazing vacation rental options in Midtown with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Midtown.
Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 723.75 ft², with prices averaging US $721 per night.
With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Midtown.
Show more
Show less
Top Pickleball-Ready Accommodation Types in Midtown
| Type | Count |
|---|---|
| Vacation Homes | 2259 |
| Holiday Apartments | 606 |
| Cottages | 112 |
| Villas | 39 |
Use these Quick Filters to Find a Vacation Rental in Midtown
★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Midtown with PickleTrip™.
Weather in Midtown, FL
View the weather forecast for Midtown before booking your Midtown Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Midtown?
What are the top vacation rentals, resorts, and hotels in Midtown with Courts?
Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Midtown. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Midtown!
- Key West Sunrise Condo - SPECIAL SUMMER RATES!
- 3 bedroom with living room and sitting room and a pool just 2 blocks from Higgs beach
- 4-bedroom resort style home in awesome Key West with large pool and private deck
- BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/Pool!
- Bahama Village Sanctuary - Family & Dog Friendly
- GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/Pool and Ocean Views!
- Old Town Key West classic with private saltwater pool & enclosed patio- by shops
- Key West Private Pool Garden Villa - 2 Blocks from Beach
- Exclusive Key West Beach Front - 2BR Luxury Condo w/Gym and Pool Access (Newly Refurnished!)
- Ocean-View Condo Shared Pool + Near Beach | Gated Community | Brisa Del Mar
How many pickleball-ready properties have private pools in Midtown?
Discover 782 accommodations with private or nearby pickleball courts in Midtown. Some of the best destinations to stay and play pickleball are:
- Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
- Key West Harbor Inn - Adults Only
- Tropical Oasis in the Truman Annex with a private pool
- Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Which vacation rentals, resorts, or hotels in Midtown is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Midtown? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.
- Tropics Escape in Key West with Onsite Pools!
- Somewhere on the beach
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
How many PickleTrip vacation rentals or resorts are available in Midtown?
PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 4684 properties listed in Midtown in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| Old Town Vacation Rentals in Key West, Florida | 1009 |
| The Meadows Vacation Rentals in Key West, Florida | 53 |
| New Town Vacation Rentals in Key West, Florida | 39 |
| White St. Gallery Vacation Rentals in Key West, Florida | 4539 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4535 |
People Also Ask
Finding the best prices in Midtown
Map
