Harold pickleball Stays, Resort Rentals, & Homes
Condo
9.6Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
1042 ft²
Oceanfront
Hot Tub
Spa
Fireplace/Heating
US $287/Night
7 Nights - US $2,011
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
1872.92 ft²
- Oceanfront
- Fireplace/Heating
Pool
Ocean View
US $372/Night
7 Nights - US $2,604
Hotel
9.8Exceptional
(490 Reviews)
1 Bath
- Pool
Balcony/Terrace
Breakfast
Pet Friendly
US $181/Night
7 Nights - US $1,266
Condo
9.4Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1134 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $305/Night
7 Nights - US $2,135
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pool
View- Breakfast
US $266/Night
7 Nights - US $1,863
House
9.6Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
11 Guests
1700 ft²
Private Pool- Fireplace/Heating
- Pool
- Ocean View
US $228/Night
7 Nights - US $1,599
New
House
1 Bedroom
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen
Parking
US $561/Night
7 Nights - US $3,928
Cottage
10.0Exceptional
(49 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $107/Night
7 Nights - US $751
House
10.0Exceptional
(47 Reviews)
1 Bedroom
1 Bath
3 Guests
400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $156/Night
7 Nights - US $1,093
Luxury Places to Stay in Harold
Over 138+ Luxury Places to Stay in or Near Harold
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $746/Night
7 Nights - US $5,222
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $643/Night
7 Nights - US $4,502
House
7.0Very Good
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
Air Conditioner
Internet
Child Friendly
Laundry
US $643/Night
7 Nights - US $4,502
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
2548 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $615/Night
7 Nights - US $4,304
House
2 Bedrooms
2 Baths
6 Guests
1130.21 ft²
- Fireplace/Heating
- Pool
- View
- Breakfast
US $568/Night
7 Nights - US $3,975
House
9.8Exceptional
(7 Reviews)
3 Bedrooms
3 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $538/Night
7 Nights - US $3,765
House
8.0Excellent
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $439/Night
7 Nights - US $3,072
House
10.0Exceptional
(14 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $425/Night
7 Nights - US $2,973
House
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- View
- Breakfast
US $414/Night
7 Nights - US $2,898
Top-Rated Villas with a Pool in Harold
Over 38+ Top-Rated Private Villas with a Pool in or Near Harold
House
10.0Exceptional
(16 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $244/Night
7 Nights - US $1,708
House
10.0Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
1439 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $225/Night
7 Nights - US $1,572
Hotel
9.5Exceptional
(205 Reviews)
13 Baths
345.27 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $177/Night
7 Nights - US $1,236
Hotel
8.6Fabulous
(737 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $161/Night
7 Nights - US $1,129
Hotel
8.6Fabulous
(109 Reviews)
9 Baths
443.72 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $159/Night
7 Nights - US $1,113
Hotel
8.6Fabulous
(62 Reviews)
1 Bath
- Pool
- Kitchen
- Parking
- Air Conditioner
US $103/Night
7 Nights - US $723
Hotel
8.2Excellent
(44 Reviews)
3 Baths
322.92 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Parking
US $95/Night
7 Nights - US $662
Hotel
8.1Excellent
(163 Reviews)
1 Bath
344.45 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $126/Night
7 Nights - US $880
Condo
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $385/Night
7 Nights - US $2,696
Pet-Friendly Villas in Harold
Over 36+ Pet-Friendly Private Villas in or Near Harold
Cabin
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $221/Night
7 Nights - US $1,550
House
9.9Exceptional
(9 Reviews)
4 Bedrooms
2 Baths
7 Guests
2400.35 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Ocean View
US $154/Night
7 Nights - US $1,077
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1540 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $233/Night
7 Nights - US $1,634
House
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1205.56 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $272/Night
7 Nights - US $1,902
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $189/Night
7 Nights - US $1,323
House
9.8Exceptional
(28 Reviews)
2 Bedrooms
1 Bath
6 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $300/Night
7 Nights - US $2,100
House
9.8Exceptional
(18 Reviews)
2 Bedrooms
1 Bath
6 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $248/Night
7 Nights - US $1,734
Cottage
9.6Exceptional
(31 Reviews)
2 Bedrooms
1 Bath
6 Guests
867 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $283/Night
7 Nights - US $1,981
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $302/Night
7 Nights - US $2,113
Large Private Villas in Harold
Over 18+ Large Villas in or Near Harold for Groups and Families
House
10.0Exceptional
(12 Reviews)
5 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $188/Night
7 Nights - US $1,317
New
House
3 Bedrooms
4 Baths
10 Guests
1969.8 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $265/Night
7 Nights - US $1,853
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
10 Guests
1500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $250/Night
7 Nights - US $1,752
House
10.0Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $247/Night
7 Nights - US $1,728
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
11 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $332/Night
7 Nights - US $2,326
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $328/Night
7 Nights - US $2,297
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $289/Night
7 Nights - US $2,022
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $252/Night
7 Nights - US $1,767
New
House
3 Bedrooms
3 Baths
12 Guests
1970 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $251/Night
7 Nights - US $1,756
Wheelchair Accessible Holiday Homes in Harold
Over 11+ Wheelchair Accessible Villas and Holiday Homes in or Near Harold
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
6 Guests
2061 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $403/Night
7 Nights - US $2,822
Condo
9.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
468 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $181/Night
7 Nights - US $1,267
Condo
8.8Fabulous
(13 Reviews)
2 Bedrooms
1 Bath
6 Guests
736 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $213/Night
7 Nights - US $1,488
Condo
4.3Average
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
1035 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $239/Night
7 Nights - US $1,673
Condo
3 Bedrooms
2 Baths
1035 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $331/Night
7 Nights - US $2,318
Condo
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $619/Night
7 Nights - US $4,334
Condo
9.8Exceptional
(64 Reviews)
2 Bedrooms
1 Bath
4 Guests
754 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $227/Night
7 Nights - US $1,588
Condo
9.8Exceptional
(61 Reviews)
1 Bedroom
2 Baths
6 Guests
803 ft²
- Spa
- Fireplace/Heating
- Pool
- Breakfast
US $317/Night
7 Nights - US $2,218
Condo
6.0Good
(1 Review)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $281/Night
7 Nights - US $1,966
Harold Villas, Airbnb and Holiday Homes Under $200
Over 33+ Harold Private Villas, Airbnb and Holiday Homes Under $200
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $179/Night
7 Nights - US $1,256
House
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
6 Guests
2012.85 ft²
- Balcony/Terrace
- View
- Parking
- Air Conditioner
US $126/Night
7 Nights - US $882
Hotel
5.6Average
(217 Reviews)
1 Bath
- Kitchen
- Parking
- Air Conditioner
- Internet
US $140/Night
7 Nights - US $980
Apartment
1 Bedroom
1 Bath
1 Guest
700 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $50/Night
7 Nights - US $351
Hotel
5.2Average
(37 Reviews)
4 Baths
279.86 ft²
- Fireplace/Heating
- View
- Breakfast
- Parking
US $120/Night
7 Nights - US $840
House
10.0Exceptional
(271 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $170/Night
7 Nights - US $1,187
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $140/Night
7 Nights - US $981
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $165/Night
7 Nights - US $1,152
House
5.0Average
(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $125/Night
7 Nights - US $875
Instantly Bookable Villa Rentals in Harold
Over 54+ Instantly Bookable Private Villas in or Near Harold
Cottage
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1015 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $276/Night
7 Nights - US $1,930
New
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $233/Night
7 Nights - US $1,632
House
10.0Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $273/Night
7 Nights - US $1,913
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $316/Night
7 Nights - US $2,211
House
9.8Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $350/Night
7 Nights - US $2,451
House
9.8Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $288/Night
7 Nights - US $2,015
House
9.6Exceptional
(15 Reviews)
4 Bedrooms
2 Baths
8 Guests
2025 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $280/Night
7 Nights - US $1,960
House
9.4Exceptional
(11 Reviews)
4 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $219/Night
7 Nights - US $1,530
House
7.0Very Good
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $213/Night
7 Nights - US $1,494
Book a Last Minute Place to Stay in Harold
About Harold Vacation Rentals
Discover over 147 amazing vacation rental options in Harold 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 Harold.
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 639.5 ft², with prices averaging US $274 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 Harold.
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Top Pickleball-Ready Accommodation Types in Harold
| Type | Count |
|---|---|
| Vacation Homes | 93 |
| Cottages | 9 |
| Holiday Apartments | 6 |
Use these Quick Filters to Find a Vacation Rental in Harold
★ 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 Harold with PickleTrip™.
Weather in Harold, FL
View the weather forecast for Harold before booking your Harold 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 Harold?
What are the top vacation rentals, resorts, and hotels in Harold 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 Harold. 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 Harold!
- El Matador 562 - FREE TICKETS! Your stay includes free tickets to many area attractions!
- Oakwood 3000 Destination vacation relaxation station extraordinaire
- El Matador 460- FREE TICKETS! Your stay includes free tickets to many area attractions!
- Quiet Getaway for 2
- Cozy Private Room-Queen&Full Bed, Hot Tub Pool Pets Welcome!
- Blackwater Bay Bungalow - Pet friendly waterfront home!
- The Mill House - a charming 3-bedroom home in tranquil Baker
- Cooper Basin River House - 35 mins to beaches
- Riverfront Milton Cabin w/Boat Ramp & Dock!
- Retro Style River house in Milton Florida on Beautiful Black Water River.
How many pickleball-ready properties have private pools in Harold?
Discover 7 accommodations with private or nearby pickleball courts in Harold. Some of the best destinations to stay and play pickleball are:
- Solar Pool & Fun|4BR Milton
- Blackwater Bay Hideaway by AvantStay | Waterfront, Pool, Dock, Hot Tub
- Okaloosa Island Family Beach Retreat!
- 2 Bedroom 1.5 Bath - With Private Condo Community Pool
Which vacation rentals, resorts, or hotels in Harold is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Harold? 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.
- RELAX ON BLACKWATER RIVER
- Waterfront Milton Home w/Boat Dock!
- El Matador 620 - FREE TICKETS! Your stay includes free tickets to many area attractions!
How many PickleTrip vacation rentals or resorts are available in Harold?
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 147 properties listed in Harold 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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