Glenwood pickleball Stays, Resort Rentals, & Homes
House
10.0Exceptional
(31 Reviews)
3 Bedrooms
2 Baths
10 Guests
4000 ft²
Private Pool
Fireplace/Heating
Pool
Ocean View
US $329/Night
7 Nights - US $2,305
Apartment
9.7Exceptional
(3 Reviews)
1 Bedroom
1 Bath
3 Guests
355.21 ft²
- Fireplace/Heating
Balcony/Terrace
View
Breakfast
US $94/Night
7 Nights - US $660
US $80/Night
7 Nights - US $560
House
10.0Exceptional
(86 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
Spa- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $154/Night
7 Nights - US $1,076
Apartment
9.6Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
7 Guests
753.47 ft²
- Fireplace/Heating
- View
- Breakfast
Parking
US $125/Night
7 Nights - US $876
House
10.0Exceptional
(72 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
US $144/Night
7 Nights - US $1,005
House
10.0Exceptional
(36 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
Air Conditioner
Internet
Child Friendly
US $78/Night
7 Nights - US $549
House
10.0Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
6 Guests
1168 ft²
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
US $207/Night
7 Nights - US $1,449
Apartment
10.0Exceptional
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $116/Night
7 Nights - US $810
Luxury Places to Stay in Glenwood
Over 133+ Luxury Places to Stay in or Near Glenwood
House
10.0Exceptional
(2 Reviews)
7 Bedrooms
3 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $997/Night
7 Nights - US $6,981
House
3 Bedrooms
3 Baths
10 Guests
4004.17 ft²
- Spa
- Fireplace/Heating
- Pool
- Pet Friendly
US $604/Night
7 Nights - US $4,230
House
- DeLand
- ·
- Rogers Deland
- 1.20 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
10 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $581/Night
7 Nights - US $4,067
House
9.6Exceptional
(74 Reviews)
5 Bedrooms
2 Baths
11 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $483/Night
7 Nights - US $3,378
House
10.0Exceptional
(14 Reviews)
3 Bedrooms
2 Baths
6 Guests
2950 ft²
Hot Tub- Fireplace/Heating
- Pool
- Ocean View
US $425/Night
7 Nights - US $2,973
New
House
4 Bedrooms
3 Baths
10 Guests
3003.13 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Child Friendly
US $371/Night
7 Nights - US $2,596
House
9.8Exceptional
(36 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $344/Night
7 Nights - US $2,411
House
- DeLand
- ·
- Hoffmann Hills
- 0.04 mi to center
9.8Exceptional
(81 Reviews)
3 Bedrooms
2 Baths
10 Guests
2700 ft²
- Private Pool
Oceanfront- Hot Tub
- Fireplace/Heating
US $338/Night
7 Nights - US $2,363
House
- DeLand
- ·
- Deleon Springs Heights
- 0.33 mi to center
9.6Exceptional
(71 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $335/Night
7 Nights - US $2,348
Top-Rated Villas with a Pool in Glenwood
Over 25+ Top-Rated Private Villas with a Pool in or Near Glenwood
Apartment
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
450 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $180/Night
7 Nights - US $1,260
Apartment
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $253/Night
7 Nights - US $1,772
House
- DeLand
- ·
- Hoffmann Hills
- 0.03 mi to center
9.8Exceptional
(118 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $303/Night
7 Nights - US $2,118
Cottage
9.8Exceptional
(63 Reviews)
3 Bedrooms
2 Baths
5 Guests
940 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $153/Night
7 Nights - US $1,073
House
9.6Exceptional
(75 Reviews)
3 Bedrooms
3 Baths
8 Guests
1650 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $324/Night
7 Nights - US $2,268
House
9.4Exceptional
(19 Reviews)
4 Bedrooms
3 Baths
8 Guests
1218 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $262/Night
7 Nights - US $1,834
Hotel
8.5Fabulous
(266 Reviews)
3 Baths
367.51 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $114/Night
7 Nights - US $798
Hotel
8.3Excellent
(140 Reviews)
4 Baths
379.43 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $179/Night
7 Nights - US $1,253
Hotel
7.7Very Good
(306 Reviews)
2 Baths
297.8 ft²
- Pool
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $117/Night
7 Nights - US $816
Pet-Friendly Villas in Glenwood
Over 39+ Pet-Friendly Private Villas in or Near Glenwood
Cottage
- DeLand
- ·
- De Leon Springs
- 2.92 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $255/Night
7 Nights - US $1,785
Hotel
8.2Excellent
(1009 Reviews)
1 Bath
- Pool
- Breakfast
- Pet Friendly
- Kitchen
US $111/Night
7 Nights - US $777
House
- DeLand
- ·
- Lasburys Sunset Terrace
- 0.06 mi to center
9.4Exceptional
(54 Reviews)
2 Bedrooms
2 Baths
8 Guests
1680 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $184/Night
7 Nights - US $1,288
House
9.4Exceptional
(25 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $172/Night
7 Nights - US $1,205
Apartment
9.4Exceptional
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $141/Night
7 Nights - US $990
Apartment
9.2Exceptional
(37 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $141/Night
7 Nights - US $990
House
9.2Exceptional
(16 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $141/Night
7 Nights - US $990
House
9.2Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
5 Guests
620 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $151/Night
7 Nights - US $1,055
Apartment
8.8Fabulous
(41 Reviews)
2 Bedrooms
1 Bath
3 Guests
900 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $141/Night
7 Nights - US $990
Large Private Villas in Glenwood
Over 14+ Large Villas in or Near Glenwood for Groups and Families
House
9.8Exceptional
(19 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $245/Night
7 Nights - US $1,715
House
- DeLand
- ·
- Richs Deland
- 0.11 mi to center
9.6Exceptional
(39 Reviews)
3 Bedrooms
2 Baths
10 Guests
2400 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $274/Night
7 Nights - US $1,920
House
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $232/Night
7 Nights - US $1,625
House
1 Bedroom
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $116/Night
7 Nights - US $812
New
House
4 Bedrooms
3 Baths
10 Guests
1980 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $219/Night
7 Nights - US $1,535
House
3 Bedrooms
3 Baths
10 Guests
- Private Pool
- Pool
- Kitchen
- Internet
US $428/Night
7 Nights - US $2,996
House
2.0Average
(1 Review)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $94/Night
7 Nights - US $659
House
3 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $792/Night
7 Nights - US $5,541
House
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $150/Night
7 Nights - US $1,050
Wheelchair Accessible Holiday Homes in Glenwood
Over 4+ Wheelchair Accessible Villas and Holiday Homes in or Near Glenwood
Hotel
8.3Excellent
(141 Reviews)
12 Baths
456.39 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $177/Night
7 Nights - US $1,241
Hotel
9.2Exceptional
(511 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $184/Night
7 Nights - US $1,290
Hotel
9.0Exceptional
(932 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $128/Night
7 Nights - US $898
Hotel
9.0Exceptional
(770 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $138/Night
7 Nights - US $964
Glenwood Villas, Airbnb and Holiday Homes Under $200
Over 64+ Glenwood Private Villas, Airbnb and Holiday Homes Under $200
House
10.0Exceptional
(22 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $165/Night
7 Nights - US $1,157
Apartment
9.5Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $68/Night
7 Nights - US $478
Hotel
9.0Exceptional
(662 Reviews)
1 Bath
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $150/Night
7 Nights - US $1,051
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $132/Night
7 Nights - US $921
House
- DeLand
- ·
- Rogers Deland
- 3.15 mi to center
2 Bedrooms
1 Bath
5 Guests
1097.92 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $134/Night
7 Nights - US $935
Cottage
- DeLand
- ·
- Deleon Springs Heights
- 0.26 mi to center
9.8Exceptional
(147 Reviews)
2 Bedrooms
1 Bath
6 Guests
600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $131/Night
7 Nights - US $918
House
9.6Exceptional
(75 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $112/Night
7 Nights - US $783
House
9.6Exceptional
(64 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $106/Night
7 Nights - US $740
Apartment
9.6Exceptional
(49 Reviews)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $153/Night
7 Nights - US $1,073
Instantly Bookable Villa Rentals in Glenwood
Over 49+ Instantly Bookable Private Villas in or Near Glenwood
Apartment
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
7 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $183/Night
7 Nights - US $1,282
Cottage
9.2Exceptional
(12 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $144/Night
7 Nights - US $1,006
House
2 Bedrooms
1 Bath
4 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $155/Night
7 Nights - US $1,085
New
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $121/Night
7 Nights - US $850
House
2 Bedrooms
1 Bath
4 Guests
1010 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $117/Night
7 Nights - US $816
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $331/Night
7 Nights - US $2,319
House
9.6Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
6 Guests
1146 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $182/Night
7 Nights - US $1,275
House
9.0Exceptional
(16 Reviews)
3 Bedrooms
2 Baths
5 Guests
1092 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $208/Night
7 Nights - US $1,455
Apartment
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $155/Night
7 Nights - US $1,085
Book a Last Minute Place to Stay in Glenwood
About Glenwood Vacation Rentals
Discover over 142 amazing vacation rental options in Glenwood 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 Glenwood.
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 642.11 ft², with prices averaging US $212 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 Glenwood.
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Top Pickleball-Ready Accommodation Types in Glenwood
| Type | Count |
|---|---|
| Vacation Homes | 93 |
| Holiday Apartments | 20 |
| Cottages | 9 |
Use these Quick Filters to Find a Vacation Rental in Glenwood
★ 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 Glenwood with PickleTrip™.
Weather in Glenwood, FL
View the weather forecast for Glenwood before booking your Glenwood 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 Glenwood?
What are the top vacation rentals, resorts, and hotels in Glenwood 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 Glenwood. 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 Glenwood!
- Beautiful Fishing Lake Front Home, Close To Beaches And Theme Parks, Sleeps 6.
- Quaint Bungalow walking distance to downtown DeLand, 2 weeks maximum Stay
- Cozy 1-bedroom 5min from Stetson university in delightful DeLand
- Riverfront DeLand Home w/Pool, Near Daytona!
- Walkable to Downtown DeLand & Stetson University - Beach 30-45 Minute Drive
- Mini Monarch 🦋 Cabina
- Cozy country home in North Deland. Close to historic downtown!
- The Studio at Casa Cascada. A ground floor studio suite in a stunning oasis
- Historic Home in the Heart of DeLand
- The Casita is a stunning villa in a tropical oasis in historic downtown DeLand.
How many pickleball-ready properties have private pools in Glenwood?
Discover 5 accommodations with private or nearby pickleball courts in Glenwood. Some of the best destinations to stay and play pickleball are:
- Beautifully Appointed Lakefront home in quiet neighborhood, with pool & hot tub
- Lovely Pool Home in Historic Town Close to Beach & Theme Parks
- 3 Mi to Dtwn DeLand: Poolside Paradise!
- Peacock House Downtown DeLand
Which vacation rentals, resorts, or hotels in Glenwood is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Glenwood? 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.
- 40'Yacht-Directly Docked on the St John's River
- Downtown DeLand Home: Walk to Stetson University!
- Tropical Resort & Marina on Lake Beresford
How many PickleTrip vacation rentals or resorts are available in Glenwood?
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 142 properties listed in Glenwood 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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