Olean pickleball Stays, Resort Rentals, & Homes
10.0
Exceptional
(212 Reviews)
- Osage Beach
- Village of Four Seasons
- 1.38 mi to center
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $189/Night
For 7 Nights US $1,324
7.0
Very Good
(2 Reviews)
- Osage Beach
- Village of Four Seasons
- 1.32 mi to center
1001.04 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $181/Night
For 7 Nights US $1,270
New
- Osage Beach
- Lake Ozark
- 2.86 mi to center
1 Bedroom
1 Bathroom
Couples Retreat
Condo
- Pool
- Parking
- Internet
US $547/Night
For 7 Nights US $3,829
10.0
Exceptional
(132 Reviews)
- Missouri
- Osage Beach
- 2.37 mi to center
960 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $223/Night
For 7 Nights US $1,563
New
- Osage Beach
- Lake Ozark
- 2.86 mi to center
1399.31 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $710/Night
For 7 Nights US $4,970
10.0
Exceptional
(104 Reviews)
- Osage Beach
- Village of Four Seasons
- 1.28 mi to center
1200 ft²
10 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Pool
- Ocean View
US $230/Night
For 7 Nights US $1,610
10.0
Exceptional
(86 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.79 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Kitchen
US $175/Night
For 7 Nights US $1,225
10.0
Exceptional
(38 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.89 mi to center
1166 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $202/Night
For 7 Nights US $1,412
10.0
Exceptional
(30 Reviews)
- Missouri
- Osage Beach
- 2.36 mi to center
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $245/Night
For 7 Nights US $1,712
Luxury Places to Stay in Olean
Over 2475+ Luxury Places to Stay in or Near Olean
9.6
Exceptional
(8 Reviews)
- Missouri
- Osage Beach
- 3.74 mi to center
5200 ft²
15 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,324/Night
For 7 Nights US $16,268
9.6
Exceptional
(4 Reviews)
- Missouri
- Osage Beach
- 3.63 mi to center
20 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- View
US $1,613/Night
For 7 Nights US $11,292
New
- Missouri
- Osage Beach
- 3.44 mi to center
4400 ft²
22 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,506/Night
For 7 Nights US $10,543
8.0
Excellent
(1 Review)
- Missouri
- Osage Beach
- 3.55 mi to center
18 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $1,109/Night
For 7 Nights US $7,763
2.0
Average
(1 Review)
- Osage Beach
- Village of Four Seasons
- 1.32 mi to center
1100 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Pet Friendly
US $1,015/Night
For 7 Nights US $7,108
2.0
Average
(1 Review)
- Osage Beach
- Village of Four Seasons
- 1.33 mi to center
1000 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $799/Night
For 7 Nights US $5,591
New
1097.92 ft²
8 Guests
2 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $593/Night
For 7 Nights US $4,149
10.0
Exceptional
(4 Reviews)
- Missouri
- Gravois Mills
- 6.00 mi to center
1800 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $571/Night
For 7 Nights US $3,995
10.0
Exceptional
(2 Reviews)
- Osage Beach
- Lake Ozark
- 2.76 mi to center
1400 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $542/Night
For 7 Nights US $3,792
Top-Rated Villas with a Pool in Olean
Over 1192+ Top-Rated Private Villas with a Pool in or Near Olean
10.0
Exceptional
(90 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.81 mi to center
2000 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $301/Night
For 7 Nights US $2,106
10.0
Exceptional
(67 Reviews)
- Osage Beach
- Lakeland
- 0.77 mi to center
1200 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $243/Night
For 7 Nights US $1,699
10.0
Exceptional
(60 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.93 mi to center
1900 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $341/Night
For 7 Nights US $2,386
10.0
Exceptional
(27 Reviews)
- Missouri
- Osage Beach
- 2.42 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $254/Night
For 7 Nights US $1,780
10.0
Exceptional
(24 Reviews)
- Osage Beach
- Shawnee Bend
- 1.20 mi to center
1800 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $237/Night
For 7 Nights US $1,660
10.0
Exceptional
(16 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.92 mi to center
1800 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Kitchen
US $253/Night
For 7 Nights US $1,772
10.0
Exceptional
(15 Reviews)
- Osage Beach
- Lakeland
- 0.76 mi to center
1600 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Private Pool
- Fireplace/Heating
- Pool
US $229/Night
For 7 Nights US $1,606
10.0
Exceptional
(13 Reviews)
- Missouri
- Osage Beach
- 2.36 mi to center
1850 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $377/Night
For 7 Nights US $2,642
10.0
Exceptional
(12 Reviews)
- Missouri
- Osage Beach
- 2.36 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $154/Night
For 7 Nights US $1,079
Pet-Friendly Villas in Olean
Over 624+ Pet-Friendly Private Villas in or Near Olean
10.0
Exceptional
(8 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.95 mi to center
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $469/Night
For 7 Nights US $3,285
New
- Osage Beach
- Village of Four Seasons
- 0.95 mi to center
1700.7 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Fireplace/Heating
- Pool
US $178/Night
For 7 Nights US $1,248
New
- Osage Beach
- Village of Four Seasons
- 0.85 mi to center
1 Bedroom
1 Bathroom
Couples Retreat
Condo
- Pool
- Pet Friendly
- Parking
US $460/Night
For 7 Nights US $3,217
10.0
Exceptional
(2 Reviews)
- Missouri
- Osage Beach
- 2.34 mi to center
900 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $178/Night
For 7 Nights US $1,246
10.0
Exceptional
(3 Reviews)
- Missouri
- Osage Beach
- 2.38 mi to center
947.22 ft²
5 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pool
- Pet Friendly
US $130/Night
For 7 Nights US $911
9.8
Exceptional
(189 Reviews)
- Osage Beach
- Village of Four Seasons
- 1.31 mi to center
1100 ft²
8 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Pool
- Ocean View
US $296/Night
For 7 Nights US $2,073
9.8
Exceptional
(16 Reviews)
- Missouri
- Osage Beach
- 2.30 mi to center
775 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $394/Night
For 7 Nights US $2,755
9.8
Exceptional
(13 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.78 mi to center
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $405/Night
For 7 Nights US $2,832
9.6
Exceptional
(22 Reviews)
- Missouri
- Gravois Mills
- 4.30 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $334/Night
For 7 Nights US $2,338
Large Private Villas in Olean
Over 807+ Large Villas in or Near Olean for Groups and Families
10.0
Exceptional
(15 Reviews)
- Missouri
- Osage Beach
- 3.21 mi to center
14 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $518/Night
For 7 Nights US $3,625
10.0
Exceptional
(10 Reviews)
- Osage Beach
- Lakeland
- 0.76 mi to center
1302.43 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
US $262/Night
For 7 Nights US $1,832
9.2
Exceptional
(12 Reviews)
- Missouri
- Rocky Mount
- 2.45 mi to center
2500 ft²
20 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,216/Night
For 7 Nights US $8,513
10.0
Exceptional
(5 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.89 mi to center
3000 ft²
11 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $351/Night
For 7 Nights US $2,460
10.0
Exceptional
(2 Reviews)
1905.21 ft²
14 Guests
3 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,014/Night
For 7 Nights US $7,100
10.0
Exceptional
(3 Reviews)
- Osage Beach
- Lake Ozark
- 3.98 mi to center
2020 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Private Pool
- Fireplace/Heating
- Pool
US $354/Night
For 7 Nights US $2,478
10.0
Exceptional
(1 Review)
- Osage Beach
- Village of Four Seasons
- 0.83 mi to center
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $270/Night
For 7 Nights US $1,890
9.8
Exceptional
(27 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.95 mi to center
1428 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $257/Night
For 7 Nights US $1,799
9.8
Exceptional
(17 Reviews)
- Osage Beach
- Lake Ozark
- 3.00 mi to center
1923 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $333/Night
For 7 Nights US $2,328
Wheelchair Accessible Holiday Homes in Olean
Over 160+ Wheelchair Accessible Villas and Holiday Homes in or Near Olean
10.0
Exceptional
(11 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.83 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $210/Night
For 7 Nights US $1,467
9.2
Exceptional
(70 Reviews)
- Osage Beach
- Lake Ozark
- 2.91 mi to center
557.57 ft²
30 Guests
7 Bathrooms
Free Cancellation
Resort
- Oceanfront
- Fireplace/Heating
- Pool
US $287/Night
For 7 Nights US $2,012
New
- Osage Beach
- Lake Ozark
- 2.60 mi to center
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $638/Night
For 7 Nights US $4,463
10.0
Exceptional
(2 Reviews)
- Osage Beach
- Lakeland
- 0.76 mi to center
1600 ft²
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $250/Night
For 7 Nights US $1,752
9.0
Exceptional
(4 Reviews)
753.47 ft²
6 Guests
2 Bedrooms
1 Bathroom
Apartment
- Pool
- Breakfast
- Parking
US $227/Night
For 7 Nights US $1,589
10.0
Exceptional
(36 Reviews)
- Osage Beach
- Lake Ozark
- 2.60 mi to center
1018 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $158/Night
For 7 Nights US $1,105
10.0
Exceptional
(28 Reviews)
- Osage Beach
- Lake Ozark
- 2.66 mi to center
1082 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $200/Night
For 7 Nights US $1,401
10.0
Exceptional
(5 Reviews)
- Osage Beach
- Lake Ozark
- 2.60 mi to center
1100 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $183/Night
For 7 Nights US $1,284
10.0
Exceptional
(2 Reviews)
- Osage Beach
- Village of Four Seasons
- 1.67 mi to center
1701 ft²
8 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $384/Night
For 7 Nights US $2,685
Olean Villas, Airbnb and Holiday Homes Under $200
Over 633+ Olean Private Villas, Airbnb and Holiday Homes Under $200
10.0
Exceptional
(2 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.66 mi to center
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $113/Night
For 7 Nights US $791
10.0
Exceptional
(9 Reviews)
8 Guests
3 Bedrooms
3 Bathrooms
House
- Pool
- Parking
- Air Conditioner
US $100/Night
For 7 Nights US $700
9.2
Exceptional
(50 Reviews)
- Missouri
- Versailles
- 0.77 mi to center
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $124/Night
For 7 Nights US $871
9.6
Exceptional
(15 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.64 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Pool
- Balcony/Terrace
US $181/Night
For 7 Nights US $1,265
10.0
Exceptional
(4 Reviews)
1334.72 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Apartment
- Fireplace/Heating
- Parking
- Internet
US $193/Night
For 7 Nights US $1,351
9.4
Exceptional
(13 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.69 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $175/Night
For 7 Nights US $1,223
9.0
Exceptional
(2 Reviews)
- Missouri
- Osage Beach
- 2.38 mi to center
950 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $152/Night
For 7 Nights US $1,065
10.0
Exceptional
(10 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.95 mi to center
1420 ft²
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $192/Night
For 7 Nights US $1,345
9.8
Exceptional
(13 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.88 mi to center
1618 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $199/Night
For 7 Nights US $1,391
Instantly Bookable Villa Rentals in Olean
Over 1496+ Instantly Bookable Private Villas in or Near Olean
10.0
Exceptional
(11 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.90 mi to center
1300 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $234/Night
For 7 Nights US $1,635
New
- Osage Beach
- Village of Four Seasons
- 0.66 mi to center
463 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $230/Night
For 7 Nights US $1,611
10.0
Exceptional
(8 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.76 mi to center
1001 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $285/Night
For 7 Nights US $1,994
10.0
Exceptional
(5 Reviews)
- Osage Beach
- Shawnee Bend
- 0.46 mi to center
900 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $340/Night
For 7 Nights US $2,377
10.0
Exceptional
(4 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.66 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $215/Night
For 7 Nights US $1,507
10.0
Exceptional
(1 Review)
- Missouri
- Osage Beach
- 3.46 mi to center
720 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Kitchen
US $248/Night
For 7 Nights US $1,737
10.0
Exceptional
(1 Review)
- Osage Beach
- Village of Four Seasons
- 1.19 mi to center
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
US $203/Night
For 7 Nights US $1,424
9.6
Exceptional
(78 Reviews)
- Osage Beach
- Lake Ozark
- 4.85 mi to center
860 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $224/Night
For 7 Nights US $1,569
9.6
Exceptional
(5 Reviews)
- Osage Beach
- Village of Four Seasons
- 0.82 mi to center
980 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $279/Night
For 7 Nights US $1,953
Book a Last Minute Place to Stay in Olean
About Olean Vacation Rentals
Discover over 2484 amazing vacation rental options in Olean 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 Olean.
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 1183.55 ft², with prices averaging US $399 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 Olean.
Show more
Show less
Top Pickleball-Ready Accommodation Types in Olean
| Type | Count |
|---|---|
| Vacation Homes | 1262 |
| Holiday Apartments | 208 |
| Villas | 35 |
| Cottages | 25 |
Use these Quick Filters to Find a Vacation Rental in Olean
★ 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 Olean with PickleTrip™.
Weather in Olean, MO
View the weather forecast for Olean before booking your Olean 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
Top Attractions Around Olean, MO
PickleTrip offers a large selection of top attractions around Olean . Research things to do on your vacation before you visit Olean.
Frequently Asked Questions About Olean?
What are the top vacation rentals, resorts, and hotels in Olean 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 Olean. 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 Olean!
- Waters Edge Condo 2B/2B GREAT location by land/water! Discounts on 7 + nights
- Breathtaking Sunsets at 17mm Lake of the Ozarks! Indian Pointe, Osage Beach, MO
- Treetop Village 14. Pet-friendly; Pool & Slips steps away; Sleeps 10
- Regatta Bay-3BD/3BA- 2 w/Lakeview. NoSteps-Great large deck- Dock incl.
- Beautiful View of Main Channel 2 Bed/2 Bath Condo w/Pools, Pickleball & Tennis!
- SUMMER NEARS! W108 Harbour Towne. Pool Opens Before Mother's Day. Kids Welcome.
- Spectacular waterfront luxury
- Lake-View Patio, Pool Access! Regatta Bay Condo
- Awesome Lakefront with Amazing Sunset views . Indian Pointe Condos Lake Ozarks
- Lakefront Stargazer - Fireplace - Desk - King & Queen Beds - Stunning Views
How many pickleball-ready properties have private pools in Olean?
Discover 125 accommodations with private or nearby pickleball courts in Olean. Some of the best destinations to stay and play pickleball are:
- Panoramic Lakefront Condo with Boat Slip
- Full Moon Condo
- Buddy's Harbor
- Top‑floor 3BR/3BA lakeview condo at Regatta Bay with vaulted ceilings, private deck, and stunning views at the 12‑Mile Marker. Optional boat slip available.
Which vacation rentals, resorts, or hotels in Olean is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Olean? 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.
- Lake-Life Condo close to Attractions & LOZ strip
- Lakefront Summer Launch Private Deck Sleep 6
- Balcony w/Marina Views: Lake Ozark Hideaway!
How many PickleTrip vacation rentals or resorts are available in Olean?
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 2484 properties listed in Olean 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.
People Also Ask
Finding the best prices in Olean
Map
