1824+ Perfect Pickle Stays with Nearby Pickleball Facilities |
Gleneagles pickleball Stays, Resort Rentals, & Homes
New
House
9.8Exceptional
(20 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
Private Pool
Fireplace/Heating
Pool
Ocean View
US $277/Night
7 Nights - US $1,936
Villa
- Naples
- ·
- East Naples
- 1.50 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
1603.82 ft²
Oceanfront- Ocean View
Balcony/Terrace
View
US $316/Night
7 Nights - US $2,212
Apartment
9.4Exceptional
(564 Reviews)
1 Bedroom
2 Baths
4 Guests
Hot Tub- Pool
- Ocean View
- Balcony/Terrace
US $419/Night
7 Nights - US $2,936
Condo
3 Bedrooms
2 Baths
6 Guests
1454 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $392/Night
7 Nights - US $2,746
Villa
- Naples
- ·
- East Naples
- 1.50 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
3 Baths
8 Guests
1603.82 ft²
- Balcony/Terrace
Pet Friendly
Parking
Air Conditioner
US $316/Night
7 Nights - US $2,212
Condo
3 Bedrooms
2 Baths
6 Guests
1454 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $341/Night
7 Nights - US $2,390
New
Condo
3 Bedrooms
2 Baths
8 Guests
1454 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $332/Night
7 Nights - US $2,324
New
Condo
2 Bedrooms
2 Baths
6 Guests
1389 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $320/Night
7 Nights - US $2,242
New
Condo
2 Bedrooms
2 Baths
6 Guests
1389 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $320/Night
7 Nights - US $2,241
Luxury Places to Stay in Gleneagles
Over 1815+ Luxury Places to Stay in or Near Gleneagles
Villa
10.0Exceptional
(1 Review)
7 Bedrooms
4 Baths
20 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,593/Night
7 Nights - US $11,150
House
10.0Exceptional
(6 Reviews)
4 Bedrooms
3 Baths
17 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,469/Night
7 Nights - US $10,280
House
10.0Exceptional
(15 Reviews)
7 Bedrooms
4 Baths
18 Guests
3900 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,310/Night
7 Nights - US $9,172
House
- Naples
- ·
- The Majors
- 0.14 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $888/Night
7 Nights - US $6,216
House
- Naples
- ·
- East Naples
- 0.26 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
8 Guests
1729 ft²
- Hot Tub
- Balcony/Terrace
- Pet Friendly
Kitchen
US $737/Night
7 Nights - US $5,161
House
4 Bedrooms
3 Baths
8 Guests
3542 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $687/Night
7 Nights - US $4,807
Condo
9.8Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Pool
- Kitchen
- Parking
US $661/Night
7 Nights - US $4,630
Condo
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
1000 ft²
- Pool
- Kitchen
- Parking
- Air Conditioner
US $650/Night
7 Nights - US $4,551
Condo
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $631/Night
7 Nights - US $4,418
Top-Rated Villas with a Pool in Gleneagles
Over 1346+ Top-Rated Private Villas with a Pool in or Near Gleneagles
House
- Naples
- ·
- Falcons Glen
- 0.07 mi to center
10.0Exceptional
(146 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Private Pool
- Oceanfront
- Hot Tub
Spa
US $256/Night
7 Nights - US $1,794
Apartment
10.0Exceptional
(76 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $151/Night
7 Nights - US $1,058
House
- Naples
- ·
- Kings Lake
- 0.28 mi to center
10.0Exceptional
(64 Reviews)
2 Bedrooms
2 Baths
4 Guests
1567 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $424/Night
7 Nights - US $2,968
Condo
10.0Exceptional
(57 Reviews)
2 Bedrooms
2 Baths
5 Guests
1351 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $132/Night
7 Nights - US $921
House
- Naples
- ·
- Crown Pointe
- 0.34 mi to center
10.0Exceptional
(52 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $290/Night
7 Nights - US $2,033
Condo
10.0Exceptional
(44 Reviews)
3 Bedrooms
2 Baths
6 Guests
1495 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $442/Night
7 Nights - US $3,095
House
- Naples
- ·
- Mustang Island
- 0.14 mi to center
10.0Exceptional
(42 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $586/Night
7 Nights - US $4,104
House
- Naples
- ·
- Crown Pointe
- 0.14 mi to center
10.0Exceptional
(38 Reviews)
4 Bedrooms
3 Baths
8 Guests
2600 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $246/Night
7 Nights - US $1,724
Condo
10.0Exceptional
(38 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $216/Night
7 Nights - US $1,512
Pet-Friendly Villas in Gleneagles
Over 326+ Pet-Friendly Private Villas in or Near Gleneagles
Condo
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
6 Guests
1244 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $210/Night
7 Nights - US $1,470
Villa
- Naples
- ·
- Lely Golf Estates
- 0.27 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
2303.48 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $828/Night
7 Nights - US $5,796
House
- Naples
- ·
- Kings Lake
- 0.22 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $887/Night
7 Nights - US $6,209
Condo
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
1137 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $116/Night
7 Nights - US $815
House
- Naples
- ·
- East Naples
- 0.26 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
8 Guests
1732.99 ft²
- Hot Tub
- Balcony/Terrace
- View
- Pet Friendly
US $544/Night
7 Nights - US $3,808
Condo
10.0Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
6 Guests
1062 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $422/Night
7 Nights - US $2,952
Condo
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $183/Night
7 Nights - US $1,282
Condo
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Pool
- Pet Friendly
- Kitchen
US $190/Night
7 Nights - US $1,331
Condo
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $241/Night
7 Nights - US $1,687
Large Private Villas in Gleneagles
Over 165+ Large Villas in or Near Gleneagles for Groups and Families
Villa
10.0Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
6 Guests
1538 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $203/Night
7 Nights - US $1,420
Villa
9.8Exceptional
(57 Reviews)
2 Bedrooms
2 Baths
6 Guests
1399.31 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $278/Night
7 Nights - US $1,946
Villa
- Naples
- ·
- East Naples
- 0.86 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $262/Night
7 Nights - US $1,831
Villa
9.6Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
1539.24 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $285/Night
7 Nights - US $1,993
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $205/Night
7 Nights - US $1,437
Villa
8.0Excellent
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1450 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $190/Night
7 Nights - US $1,328
Villa
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $366/Night
7 Nights - US $2,564
Villa
- Naples
- ·
- East Naples
- 1.19 mi to center
2 Bedrooms
2 Baths
4 Guests
1565 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $262/Night
7 Nights - US $1,834
Villa
2 Bedrooms
2 Baths
6 Guests
1387 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $185/Night
7 Nights - US $1,292
Wheelchair Accessible Holiday Homes in Gleneagles
Over 134+ Wheelchair Accessible Villas and Holiday Homes in or Near Gleneagles
Condo
2 Bedrooms
2 Baths
6 Guests
1661 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $186/Night
7 Nights - US $1,303
Apartment
9.4Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
US $251/Night
7 Nights - US $1,755
Hotel
- Naples
- ·
- Isles of Collier Preserve
- 0.21 mi to center
9.8Exceptional
(471 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $107/Night
7 Nights - US $746
Condo
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $164/Night
7 Nights - US $1,150
House
- Naples
- ·
- Kings Lake
- 0.28 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1603.82 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $416/Night
7 Nights - US $2,912
Condo
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1408 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $287/Night
7 Nights - US $2,007
Condo
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1137 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $183/Night
7 Nights - US $1,282
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $218/Night
7 Nights - US $1,528
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $164/Night
7 Nights - US $1,149
Gleneagles Villas, Airbnb and Holiday Homes Under $200
Over 553+ Gleneagles Private Villas, Airbnb and Holiday Homes Under $200
Apartment
- Naples
- ·
- East Naples
- 0.69 mi to center
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Parking
US $197/Night
7 Nights - US $1,382
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- View
- Parking
US $124/Night
7 Nights - US $868
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $178/Night
7 Nights - US $1,247
House
- Naples
- ·
- Crown Pointe
- 0.27 mi to center
3 Bedrooms
2 Baths
6 Guests
1450 ft²
- Oceanfront
- Spa
- Pool
- Ocean View
US $178/Night
7 Nights - US $1,244
Apartment
10.0Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
1011.81 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $181/Night
7 Nights - US $1,267
Condo
10.0Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
1389 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $181/Night
7 Nights - US $1,267
Condo
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $174/Night
7 Nights - US $1,220
Condo
- Naples
- ·
- East Naples
- 0.44 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
4 Guests
1540 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $128/Night
7 Nights - US $899
Condo
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $195/Night
7 Nights - US $1,362
Instantly Bookable Villa Rentals in Gleneagles
Over 853+ Instantly Bookable Private Villas in or Near Gleneagles
Condo
2 Bedrooms
2 Baths
4 Guests
1389 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $273/Night
7 Nights - US $1,910
Apartment
1 Bedroom
1 Bath
- Air Conditioner
- Child Friendly
Laundry
Bedding/Linens
US $529/Night
7 Nights - US $3,703
Condo
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
6 Guests
1389 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $219/Night
7 Nights - US $1,531
Condo
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
1496 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $259/Night
7 Nights - US $1,816
Condo
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $203/Night
7 Nights - US $1,421
Condo
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Pool
- Ocean View
- View
- Kitchen
US $135/Night
7 Nights - US $944
Condo
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $161/Night
7 Nights - US $1,127
Condo
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1350 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $155/Night
7 Nights - US $1,086
Condo
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1389 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $268/Night
7 Nights - US $1,878
Book a Last Minute Place to Stay in Gleneagles
About Gleneagles Vacation Rentals
Discover over 1824 amazing vacation rental options in Gleneagles 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 Gleneagles.
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 991.88 ft², with prices averaging US $302 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 Gleneagles.
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Top Pickleball-Ready Accommodation Types in Gleneagles
| Type | Count |
|---|---|
| Vacation Homes | 745 |
| Holiday Apartments | 121 |
| Villas | 114 |
| Cottages | 13 |
Use these Quick Filters to Find a Vacation Rental in Gleneagles
★ 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 Gleneagles with PickleTrip™.
Weather in Gleneagles, FL
View the weather forecast for Gleneagles before booking your Gleneagles 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 Gleneagles?
What are the top vacation rentals, resorts, and hotels in Gleneagles 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 Gleneagles. 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 Gleneagles!
- New Updates Lely Resort, 3 bed, golf course home Includes Players Club and Spa
- Lovely 2-Bedroom + Den Condo in Greenlinks Resort
- VILLA BELLY :-) heated pool. free WIFI, very private, Garage, BBQ, Kings Lake
- Generously sized updated lanai showcasing a prime mid-water south view.
- Beautiful Updated Home, Private Pool, Minutes from Downtown 5th Ave & Beaches!
- PLAYERS CLUB AVAILABLE, Professionally Renovated, 3 Bedroom Golf Condo
- Welcome to your luxury vacation retreat in the prestigious Majors at Lely Resort
- Luxury Crown Pointe pool & lake view home minutes to beaches & Old Naples
- NEW Luxury 3 BR Greenlinks Condo totally remodeled! Sleeps 8!
- Luxury Golf Villa in Beautiful Lely Resort w/Pool
How many pickleball-ready properties have private pools in Gleneagles?
Discover 384 accommodations with private or nearby pickleball courts in Gleneagles. Some of the best destinations to stay and play pickleball are:
- Water view condo w/access to community amenities, wifi, & outdoor private patio
- Updated condo with large lanai + outdoor kitchen. Water view at Magnolia Falls.
- Townhouse in South Naples, Lely resort OLE
- Luxurious Lake Front Condo 2/2, First Floor Unit
Which vacation rentals, resorts, or hotels in Gleneagles is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Gleneagles? 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.
- Booking Jan-April 2026 NOW! Lely 2BR 2BATH +Den Lely Golf & Swim Condo! A+
- Isles of Collier, Pickleball, Tennis, Pool, Hike
- Genoa Vacation Rental: Stylish 2-BR Condo with Golf & Lake Views. Resort-Style Pool, Hot Tub, and Easy Access to Championship Golf. Minutes from Naples Beaches, 5th Avenue S, and Marco Island
How many PickleTrip vacation rentals or resorts are available in Gleneagles?
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 1824 properties listed in Gleneagles 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 (1)
| Neighborhood | Property Count |
|---|---|
| Lely Golf Estates Vacation Rentals in Naples, Florida | 38 |
People Also Ask
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