Maidstone pickleball Stays, Resort Rentals, & Homes
House
- St. Petersburg - Clearwater
- ·
- Largo
- 3.55 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
Parking
Pool
Balcony/Terrace
Kitchen
US $141/Night
7 Nights - US $984
House
- St. Petersburg - Clearwater
- ·
- Largo
- 2.28 mi to center
5 Bedrooms
3 Baths
18 Guests
1862.16 ft²
Oceanfront- Parking
- Pool
Ocean View
US $949/Night
7 Nights - US $6,643
Cottage
- St. Petersburg - Clearwater
- ·
- Seminole
- 1.31 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Parking
- Pool
- Ocean View
US $536/Night
7 Nights - US $3,755
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.88 mi to center
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
Internet
Child Friendly
US $281/Night
7 Nights - US $1,964
House
- St. Petersburg - Clearwater
- ·
- Largo
- 1.15 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1539.24 ft²
- Oceanfront
Hot Tub- Parking
- Pool
US $296/Night
7 Nights - US $2,072
Condo
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.93 mi to center
2 Bedrooms
2 Baths
4 Guests
975 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $242/Night
7 Nights - US $1,693
US $144/Night
7 Nights - US $1,011
House
- St. Petersburg - Clearwater
- ·
- Largo
- 0.71 mi to center
2 Bedrooms
2 Baths
6 Guests
Air Conditioner- Internet
Laundry
Wellness Facilities
US $116/Night
7 Nights - US $809
House
- St. Petersburg - Clearwater
- ·
- Somerset Lakes
- 0.26 mi to center
10.0Exceptional
(62 Reviews)
3 Bedrooms
2 Baths
6 Guests
1000 ft²
Private Pool- Oceanfront
- Hot Tub
- Parking
US $328/Night
7 Nights - US $2,296
Luxury Places to Stay in Maidstone
Over 902+ Luxury Places to Stay in or Near Maidstone
House
- St. Petersburg - Clearwater
- ·
- Walsingham
- 0.61 mi to center
9.4Exceptional
(3 Reviews)
6 Bedrooms
4 Baths
10 Guests
2546 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $774/Night
7 Nights - US $5,415
House
- St. Petersburg - Clearwater
- ·
- Pinebrook Estates
- 0.26 mi to center
9.6Exceptional
(9 Reviews)
5 Bedrooms
2 Baths
20 Guests
1866 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $758/Night
7 Nights - US $5,305
House
- St. Petersburg - Clearwater
- ·
- Largo
- 1.34 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
2146 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $574/Night
7 Nights - US $4,018
House
- St. Petersburg - Clearwater
- ·
- Largo
- 1.85 mi to center
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $549/Night
7 Nights - US $3,845
House
- St. Petersburg - Clearwater
- ·
- Pinebrook Estates
- 0.22 mi to center
10.0Exceptional
(32 Reviews)
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $403/Night
7 Nights - US $2,823
House
- St. Petersburg - Clearwater
- ·
- Largo
- 3.18 mi to center
9.8Exceptional
(24 Reviews)
3 Bedrooms
1 Bath
7 Guests
2000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $367/Night
7 Nights - US $2,568
New
House
- St. Petersburg - Clearwater
- ·
- Largo
- 1.16 mi to center
5 Bedrooms
2 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $188/Night
7 Nights - US $1,313
New
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.77 mi to center
4 Bedrooms
2 Baths
14 Guests
1603.82 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $6,117/Night
7 Nights - US $42,818
Cottage
- St. Petersburg - Clearwater
- ·
- Walsingham
- 0.65 mi to center
1 Bedroom
1 Bath
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $3,154/Night
7 Nights - US $22,078
Top-Rated Villas with a Pool in Maidstone
Over 489+ Top-Rated Private Villas with a Pool in or Near Maidstone
Condo
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.93 mi to center
10.0Exceptional
(109 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $263/Night
7 Nights - US $1,842
Condo
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.91 mi to center
10.0Exceptional
(104 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $281/Night
7 Nights - US $1,966
House
- St. Petersburg - Clearwater
- ·
- Pinellas Park
- 1.10 mi to center
10.0Exceptional
(102 Reviews)
4 Bedrooms
1 Bath
10 Guests
924 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $290/Night
7 Nights - US $2,032
Condo
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.91 mi to center
10.0Exceptional
(82 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $272/Night
7 Nights - US $1,903
House
- St. Petersburg - Clearwater
- ·
- Pinellas Park
- 1.79 mi to center
10.0Exceptional
(81 Reviews)
3 Bedrooms
2 Baths
10 Guests
1867 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $280/Night
7 Nights - US $1,960
House
- St. Petersburg - Clearwater
- ·
- Walsingham
- 0.50 mi to center
10.0Exceptional
(41 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $290/Night
7 Nights - US $2,028
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.41 mi to center
10.0Exceptional
(34 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $465/Night
7 Nights - US $3,254
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 1.71 mi to center
10.0Exceptional
(27 Reviews)
3 Bedrooms
2 Baths
8 Guests
12228 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $490/Night
7 Nights - US $3,429
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.95 mi to center
10.0Exceptional
(21 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $487/Night
7 Nights - US $3,412
Pet-Friendly Villas in Maidstone
Over 420+ Pet-Friendly Private Villas in or Near Maidstone
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.84 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $202/Night
7 Nights - US $1,412
House
- St. Petersburg - Clearwater
- ·
- Pinellas Park
- 0.44 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
882.64 ft²
- Parking
- Pool
View- Air Conditioner
US $518/Night
7 Nights - US $3,624
Villa
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.20 mi to center
8.4Excellent
(5 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $79/Night
7 Nights - US $551
House
- St. Petersburg - Clearwater
- ·
- Largo
- 1.69 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
1 Bath
8 Guests
960 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $378/Night
7 Nights - US $2,644
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 1.96 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1302.43 ft²
Private Beach- Oceanfront
- Parking
- Pool
US $293/Night
7 Nights - US $2,048
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.86 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $318/Night
7 Nights - US $2,228
Apartment
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.21 mi to center
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $265/Night
7 Nights - US $1,855
Villa
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.16 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
910 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $151/Night
7 Nights - US $1,054
House
- St. Petersburg - Clearwater
- ·
- Orange Lake Village
- 0.09 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $245/Night
7 Nights - US $1,713
Large Private Villas in Maidstone
Over 236+ Large Villas in or Near Maidstone for Groups and Families
Villa
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.50 mi to center
10.0Exceptional
(15 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $176/Night
7 Nights - US $1,233
House
- St. Petersburg - Clearwater
- ·
- Largo
- 0.99 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
10 Guests
75.35 ft²
- Oceanfront
Breakfast- Parking
- Pool
US $291/Night
7 Nights - US $2,039
House
- St. Petersburg - Clearwater
- ·
- Largo
- 1.56 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
11 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $530/Night
7 Nights - US $3,709
Villa
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.39 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1050 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $181/Night
7 Nights - US $1,268
Villa
- St. Petersburg - Clearwater
- ·
- Largo
- 1.09 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1194.79 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $261/Night
7 Nights - US $1,826
Villa
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.12 mi to center
2 Bedrooms
2 Baths
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $169/Night
7 Nights - US $1,181
House
- St. Petersburg - Clearwater
- ·
- Largo
- 0.73 mi to center
10.0Exceptional
(14 Reviews)
4 Bedrooms
2 Baths
10 Guests
1539 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $399/Night
7 Nights - US $2,795
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 1.58 mi to center
10.0Exceptional
(13 Reviews)
3 Bedrooms
4 Baths
10 Guests
3725 ft²
- Parking
- Kitchen
- Air Conditioner
- Child Friendly
US $615/Night
7 Nights - US $4,304
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 1.12 mi to center
10.0Exceptional
(12 Reviews)
7 Bedrooms
5 Baths
28 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $1,128/Night
7 Nights - US $7,896
Wheelchair Accessible Holiday Homes in Maidstone
Over 16+ Wheelchair Accessible Villas and Holiday Homes in or Near Maidstone
House
- St. Petersburg - Clearwater
- ·
- Walsingham
- 0.50 mi to center
6.6Good
(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
1595 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $615/Night
7 Nights - US $4,304
House
- St. Petersburg - Clearwater
- ·
- Largo
- 0.80 mi to center
9.5Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
1582.29 ft²
- Parking
- Pool
- View
- Air Conditioner
US $425/Night
7 Nights - US $2,975
Hotel
- St. Petersburg - Clearwater
- ·
- Largo
- 0.35 mi to center
9.4Exceptional
(1021 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $125/Night
7 Nights - US $876
House
- St. Petersburg - Clearwater
- ·
- Walsingham
- 0.54 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $329/Night
7 Nights - US $2,303
House
- St. Petersburg - Clearwater
- ·
- Largo
- 2.38 mi to center
8.5Fabulous
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
1205.56 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $373/Night
7 Nights - US $2,611
House
- St. Petersburg - Clearwater
- ·
- Pinebrook Estates
- 0.13 mi to center
9.6Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $240/Night
7 Nights - US $1,683
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 1.60 mi to center
4.8Average
(25 Reviews)
3 Bedrooms
2 Baths
9 Guests
1800 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $428/Night
7 Nights - US $2,996
House
- St. Petersburg - Clearwater
- ·
- Pinellas Park
- 1.49 mi to center
4.0Average
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $138/Night
7 Nights - US $966
House
- St. Petersburg - Clearwater
- ·
- Pinellas Park
- 1.25 mi to center
2.7Average
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $213/Night
7 Nights - US $1,491
Maidstone Villas, Airbnb and Holiday Homes Under $200
Over 224+ Maidstone Private Villas, Airbnb and Holiday Homes Under $200
Apartment
- St. Petersburg - Clearwater
- ·
- Largo
- 2.20 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $116/Night
7 Nights - US $812
House
- St. Petersburg - Clearwater
- ·
- Largo
- 2.26 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
1001.04 ft²
- Parking
- View
- Air Conditioner
- Internet
US $134/Night
7 Nights - US $936
Hotel
- St. Petersburg - Clearwater
- ·
- Largo
- 3.58 mi to center
6.8Good
(597 Reviews)
1 Bath
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $111/Night
7 Nights - US $775
Condo
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.93 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
922 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $177/Night
7 Nights - US $1,236
Apartment
- St. Petersburg - Clearwater
- ·
- Pinellas Park
- 1.55 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
355.21 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $80/Night
7 Nights - US $560
Apartment
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.22 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $167/Night
7 Nights - US $1,168
Apartment
- St. Petersburg - Clearwater
- ·
- Seminole
- 1.11 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,396
House
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.20 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
1399 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,319
House
- St. Petersburg - Clearwater
- ·
- Largo
- 1.72 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
1 Guest
700 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $172/Night
7 Nights - US $1,202
Instantly Bookable Villa Rentals in Maidstone
Over 552+ Instantly Bookable Private Villas in or Near Maidstone
House
- St. Petersburg - Clearwater
- ·
- Largo
- 2.26 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $233/Night
7 Nights - US $1,634
House
- St. Petersburg - Clearwater
- ·
- Orange Lake Village
- 0.09 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $158/Night
7 Nights - US $1,109
House
- St. Petersburg - Clearwater
- ·
- Orange Lake Village
- 0.24 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1900 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $415/Night
7 Nights - US $2,903
House
- St. Petersburg - Clearwater
- ·
- Largo
- 1.62 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $479/Night
7 Nights - US $3,354
House
- St. Petersburg - Clearwater
- ·
- Largo
- 0.36 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
3 Baths
6 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $307/Night
7 Nights - US $2,147
House
- St. Petersburg - Clearwater
- ·
- Pinellas Park
- 0.98 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $234/Night
7 Nights - US $1,637
Cabin
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.67 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,396
Cabin
- St. Petersburg - Clearwater
- ·
- Seminole
- 1.13 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,313
Cabin
- St. Petersburg - Clearwater
- ·
- Seminole
- 0.93 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $183/Night
7 Nights - US $1,278
Book a Last Minute Place to Stay in Maidstone
About Maidstone Vacation Rentals
Discover over 911 amazing vacation rental options in Maidstone 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 Maidstone.
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 989.35 ft², with prices averaging US $354 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 Maidstone.
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Top Pickleball-Ready Accommodation Types in Maidstone
| Type | Count |
|---|---|
| Vacation Homes | 770 |
| Holiday Apartments | 64 |
| Villas | 19 |
| Cottages | 10 |
Use these Quick Filters to Find a Vacation Rental in Maidstone
★ 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 Maidstone with PickleTrip™.
Weather in Maidstone, FL
View the weather forecast for Maidstone before booking your Maidstone 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 Maidstone?
What are the top vacation rentals, resorts, and hotels in Maidstone 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 Maidstone. 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 Maidstone!
- Pool Home with Pool Heater and Hot Tub Near Clearwater and other Fine Beaches.
- Your pet friendly Tampa pool home, right between the beaches and Tampa proper!
- NEW LISTING! Relaxing 1BR Retreat with Pool, 15 Mins from the Beach
- Resort-Style Oasis Pool Mini Golf Playground
- Tropical Beach Town Private Pool Home Oasis & Tiki Lanai Close to Beaches!
- Hibiscus16 Heated Pool Mins to Beaches 2 mins walk to Pickleball/Tennis court
- Basketball | Pickleball | Pool | Movie & Game Room
- Hibiscus16 Heated Pool, Near Beach, Farmer Markets, Tampa, Clearwater, Pinellas Park, Pickleball, Tennis
- Beach & Jungle + Pool + Mini Golf+ Basketball
- Serene Lakeside Home Near Beach
How many pickleball-ready properties have private pools in Maidstone?
Discover 296 accommodations with private or nearby pickleball courts in Maidstone. Some of the best destinations to stay and play pickleball are:
- Backyard Oasis Minutes To Beaches
- Largo Pool House and Firepit
- Charming 2-bedroom house with Pool.
- One Palm Pool House- Close to the Beach!
Which vacation rentals, resorts, or hotels in Maidstone is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Maidstone? 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.
- Backyard Oasis Minutes To Beaches
- 3 Bedroom House with pool, 10 min from the beach
- Fire Pit! Family Getaway, 6 Mi to Beach Access
How many PickleTrip vacation rentals or resorts are available in Maidstone?
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 911 properties listed in Maidstone 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.
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