Oakland pickleball Stays, Resort Rentals, & Homes
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.54 mi to center
9.8Exceptional
(112 Reviews)
1 Bedroom
1 Bath
5 Guests
1000 ft²
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $135/Night
7 Nights - US $946
Apartment
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
Air Conditioner
Internet
Child Friendly
US $686/Night
7 Nights - US $4,800
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
7.6Very Good
(147 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $211/Night
7 Nights - US $1,474
Apartment
- Chicago
- ·
- Bronzeville
- 0.42 mi to center
10.0Exceptional
(32 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
Oceanfront- Parking
Ocean View- Balcony/Terrace
US $212/Night
7 Nights - US $1,486
Apartment
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1851.39 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $287/Night
7 Nights - US $2,007
Apartment
- Chicago
- ·
- North Kenwood
- 0.10 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $359/Night
7 Nights - US $2,510
Apartment
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
Spa- Ocean View
- Balcony/Terrace
US $212/Night
7 Nights - US $1,481
House
- Chicago
- ·
- Prairie District
- 0.14 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
5 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $884/Night
7 Nights - US $6,185
Apartment
- Chicago
- ·
- Bridgeport
- 0.46 mi to center
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $287/Night
7 Nights - US $2,012
Luxury Places to Stay in Oakland
Over 1160+ Luxury Places to Stay in or Near Oakland
New
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
6 Bedrooms
4 Baths
12 Guests
1603.82 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $4,976/Night
7 Nights - US $34,831
New
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
3 Baths
12 Guests
1496.18 ft²
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
US $4,545/Night
7 Nights - US $31,814
Hotel
8.9Fabulous
(209 Reviews)
4 Baths
349.83 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Air Conditioner
US $2,333/Night
7 Nights - US $16,331
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
4 Baths
12 Guests
2303.48 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $2,198/Night
7 Nights - US $15,383
House
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,184/Night
7 Nights - US $15,288
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
12 Guests
2723.27 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $2,158/Night
7 Nights - US $15,106
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
3 Baths
12 Guests
1851.39 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $2,119/Night
7 Nights - US $14,833
House
- Chicago
- ·
- Bridgeport
- 0.68 mi to center
8.8Fabulous
(7 Reviews)
7 Bedrooms
5 Baths
16 Guests
4499.31 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $1,785/Night
7 Nights - US $12,497
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.4Exceptional
(16 Reviews)
3 Bedrooms
2 Baths
8 Guests
2368.06 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $1,466/Night
7 Nights - US $10,262
Top-Rated Villas with a Pool in Oakland
Over 49+ Top-Rated Private Villas with a Pool in or Near Oakland
House
- Chicago
- ·
- Bronzeville
- 0.38 mi to center
9.6Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
6 Guests
1500 ft²
Private Pool- Parking
Pool- Balcony/Terrace
US $389/Night
7 Nights - US $2,722
Hotel
- Chicago
- ·
- Near South Side
- 0.41 mi to center
9.2Exceptional
(938 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
US $468/Night
7 Nights - US $3,279
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
9.0Exceptional
(1008 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $242/Night
7 Nights - US $1,691
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.6Fabulous
(1004 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $272/Night
7 Nights - US $1,906
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.6Fabulous
(268 Reviews)
1 Bath
301.39 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $291/Night
7 Nights - US $2,035
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.5Fabulous
(730 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $229/Night
7 Nights - US $1,604
Hotel
8.3Excellent
(360 Reviews)
5 Baths
363.82 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $171/Night
7 Nights - US $1,197
House
- Chicago
- ·
- Grand Boulevard
- 0.32 mi to center
8.3Excellent
(12 Reviews)
6 Bedrooms
5 Baths
15 Guests
3196.88 ft²
- Parking
- Pool
- Balcony/Terrace
View
US $657/Night
7 Nights - US $4,597
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.0Excellent
(359 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $162/Night
7 Nights - US $1,133
Pet-Friendly Villas in Oakland
Over 306+ Pet-Friendly Private Villas in or Near Oakland
Apartment
- Chicago
- ·
- Lower West Side
- 1.59 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $384/Night
7 Nights - US $2,691
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- View
- Air Conditioner
- Internet
- Pet Friendly
US $385/Night
7 Nights - US $2,692
Condo
- Chicago
- ·
- Grand Boulevard
- 0.49 mi to center
1 Bedroom
1 Bath
- Kitchen
- Internet
- Pet Friendly
Laundry
US $180/Night
7 Nights - US $1,259
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Internet
- Pet Friendly
- Child Friendly
US $181/Night
7 Nights - US $1,266
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Air Conditioner
- Internet
- Pet Friendly
Wheelchair Accessible
US $351/Night
7 Nights - US $2,454
Condo
- Chicago
- ·
- South Loop
- 0.15 mi to center
9.8Exceptional
(54 Reviews)
2 Bedrooms
2 Baths
6 Guests
958 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $381/Night
7 Nights - US $2,665
Apartment
9.8Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $250/Night
7 Nights - US $1,750
Apartment
- Chicago
- ·
- South Loop
- 0.21 mi to center
9.4Exceptional
(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
958 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $361/Night
7 Nights - US $2,529
Apartment
- Chicago
- ·
- Bridgeport
- 0.29 mi to center
8.8Fabulous
(21 Reviews)
1 Bedroom
1 Bath
4 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $218/Night
7 Nights - US $1,528
Large Private Villas in Oakland
Over 148+ Large Villas in or Near Oakland for Groups and Families
Apartment
- Chicago
- ·
- Back of the Yards
- 0.61 mi to center
1 Bedroom
1 Bath
16 Guests
- Air Conditioner
- Child Friendly
Security/Safety
US $172/Night
7 Nights - US $1,205
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1119.45 ft²
- EV Charge Station
- Parking
- Spa
- Air Conditioner
US $439/Night
7 Nights - US $3,070
Apartment
- Chicago
- ·
- Armour Square
- 0.77 mi to center
10.0Exceptional
(25 Reviews)
4 Bedrooms
1 Bath
12 Guests
1100 ft²
- Parking
- Kitchen
- Internet
- Child Friendly
US $543/Night
7 Nights - US $3,799
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.5Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1097.92 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $414/Night
7 Nights - US $2,898
House
10.0Exceptional
(22 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $769/Night
7 Nights - US $5,381
Condo
10.0Exceptional
(20 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $623/Night
7 Nights - US $4,359
House
10.0Exceptional
(16 Reviews)
5 Bedrooms
3 Baths
8 Guests
4000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $851/Night
7 Nights - US $5,957
House
10.0Exceptional
(11 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $609/Night
7 Nights - US $4,264
House
- Chicago
- ·
- Bridgeport
- 0.76 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $631/Night
7 Nights - US $4,419
Wheelchair Accessible Holiday Homes in Oakland
Over 404+ Wheelchair Accessible Villas and Holiday Homes in or Near Oakland
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $174/Night
7 Nights - US $1,219
Apartment
- Chicago
- ·
- East Hyde Park
- 0.14 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Ocean View
- View
- Air Conditioner
- Internet
US $54/Night
7 Nights - US $378
Hotel
9.6Exceptional
(1009 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $266/Night
7 Nights - US $1,865
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $160/Night
7 Nights - US $1,117
Apartment
- Chicago
- ·
- East Hyde Park
- 0.22 mi to center
9.5Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1001.04 ft²
- Ocean View
- View
- Air Conditioner
- Internet
US $86/Night
7 Nights - US $602
Apartment
- Chicago
- ·
- Prairie District
- 0.03 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $138/Night
7 Nights - US $969
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
8 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,102
Apartment
- Chicago
- ·
- Near South Side
- 0.41 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $224/Night
7 Nights - US $1,570
Apartment
- Chicago
- ·
- Near South Side
- 0.14 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $187/Night
7 Nights - US $1,308
Oakland Villas, Airbnb and Holiday Homes Under $200
Over 396+ Oakland Private Villas, Airbnb and Holiday Homes Under $200
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.20 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Air Conditioner
- Internet
- Child Friendly
US $172/Night
7 Nights - US $1,201
Apartment
- Chicago
- ·
- South Loop
- 0.22 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
441.32 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $185/Night
7 Nights - US $1,295
House
- Chicago
- ·
- Bronzeville
- 0.35 mi to center
6.6Good
(104 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $125/Night
7 Nights - US $875
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $174/Night
7 Nights - US $1,219
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.60 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
9687.52 ft²
- Air Conditioner
- Internet
- Child Friendly
US $180/Night
7 Nights - US $1,260
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,318
Apartment
- Chicago
- ·
- Near South Side
- 0.48 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $174/Night
7 Nights - US $1,219
Apartment
- Chicago
- ·
- Near South Side
- 0.40 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $167/Night
7 Nights - US $1,167
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $167/Night
7 Nights - US $1,167
Instantly Bookable Villa Rentals in Oakland
Over 582+ Instantly Bookable Private Villas in or Near Oakland
Apartment
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
905 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $408/Night
7 Nights - US $2,859
Bed & Breakfast
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
237 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $194/Night
7 Nights - US $1,357
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $242/Night
7 Nights - US $1,693
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $230/Night
7 Nights - US $1,611
Apartment
- Chicago
- ·
- Bridgeport
- 0.56 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $267/Night
7 Nights - US $1,872
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $167/Night
7 Nights - US $1,167
Apartment
- Chicago
- ·
- Bridgeport
- 0.48 mi to center
9.8Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
861 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $223/Night
7 Nights - US $1,561
Condo
- Chicago
- ·
- Grand Boulevard
- 0.66 mi to center
9.6Exceptional
(29 Reviews)
1 Bedroom
1 Bath
2 Guests
- Internet
- Child Friendly
Bedding/Linens
Wellness Facilities
US $320/Night
7 Nights - US $2,237
Apartment
- Chicago
- ·
- Bridgeport
- 0.70 mi to center
9.6Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
1200 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $245/Night
7 Nights - US $1,714
Book a Last Minute Place to Stay in Oakland
About Oakland Vacation Rentals
Discover over 1169 amazing vacation rental options in Oakland 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 Oakland.
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 799.79 ft², with prices averaging US $409 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 Oakland.
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Top Pickleball-Ready Accommodation Types in Oakland
| Type | Count |
|---|---|
| Holiday Apartments | 839 |
| Vacation Homes | 135 |
| Cottages | 2 |
| Villas | 2 |
Use these Quick Filters to Find a Vacation Rental in Oakland
★ 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 Oakland with PickleTrip™.
Weather in Oakland, IL
View the weather forecast for Oakland before booking your Oakland 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
Other Places to Stay in Oakland, IL
Frequently Asked Questions About Oakland?
What are the top vacation rentals, resorts, and hotels in Oakland 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 Oakland. 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 Oakland!
- Lg Studio Apt. No cleaning fee. Obama Center 10 mins.
- Toca Bella ~ 7mins to Downtown
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Penthouse, Lux stay near Downtown, McComick & Lake
- Large historic home minutes from downtown Chicago and the lakefront.
- Bronzeville-Lakefront property, near Sox, McCormick, Museums & Downtown Chicago.
- The Landmark; a comfy suite near McCormick Place
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
Which vacation rentals, resorts, or hotels in Oakland is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Oakland? 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.
- Spacious unit in historic gem
- Cozy 3BR City Living in South Loop Near McCormick Place, Soldier Field & Lakefront
- Sophy Hyde Park
How many PickleTrip vacation rentals or resorts are available in Oakland?
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 1169 properties listed in Oakland 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 (2)
| Neighborhood | Property Count |
|---|---|
| Bronzeville Vacation Rentals in Chicago, Illinois | 78 |
| North Kenwood Vacation Rentals in Chicago, Illinois | 777 |
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