Caldecott 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
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
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
House
3 Bedrooms
2 Baths
6 Guests
1603.82 ft²
Parking
Air Conditioner
Internet
Child Friendly
US $565/Night
7 Nights - US $3,957
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 Caldecott
Over 1392+ Luxury Places to Stay in or Near Caldecott
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
- 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
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
House
- Naples
- ·
- Falcons Glen
- 0.07 mi to center
9.2Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
2034 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $618/Night
7 Nights - US $4,323
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
2100 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $602/Night
7 Nights - US $4,211
Top-Rated Villas with a Pool in Caldecott
Over 1067+ Top-Rated Private Villas with a Pool in or Near Caldecott
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
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
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
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
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
House
- Naples
- ·
- Falcons Glen
- 0.11 mi to center
10.0Exceptional
(31 Reviews)
3 Bedrooms
2 Baths
6 Guests
1750 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $351/Night
7 Nights - US $2,455
Condo
10.0Exceptional
(27 Reviews)
3 Bedrooms
2 Baths
6 Guests
1454 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $472/Night
7 Nights - US $3,302
Pet-Friendly Villas in Caldecott
Over 217+ Pet-Friendly Private Villas in or Near Caldecott
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
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $178/Night
7 Nights - US $1,247
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
Apartment
9.9Exceptional
(24 Reviews)
2 Bedrooms
2 Baths
5 Guests
1248.61 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $269/Night
7 Nights - US $1,882
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 Caldecott
Over 111+ Large Villas in or Near Caldecott for Groups and Families
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
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
9.4Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1555 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $285/Night
7 Nights - US $1,993
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
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
1387 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $185/Night
7 Nights - US $1,292
Villa
2 Bedrooms
2 Baths
4 Guests
1204 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $175/Night
7 Nights - US $1,228
Villa
2 Bedrooms
2 Baths
6 Guests
1643 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $158/Night
7 Nights - US $1,107
Villa
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $404/Night
7 Nights - US $2,831
Wheelchair Accessible Holiday Homes in Caldecott
Over 114+ Wheelchair Accessible Villas and Holiday Homes in or Near Caldecott
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
9.6Exceptional
(42 Reviews)
2 Bedrooms
2 Baths
5 Guests
1345.49 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $198/Night
7 Nights - US $1,388
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
9.5Exceptional
(48 Reviews)
3 Bedrooms
2 Baths
8 Guests
1388.54 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $605/Night
7 Nights - US $4,235
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
4 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $164/Night
7 Nights - US $1,149
Condo
9.6Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
6 Guests
1137 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $170/Night
7 Nights - US $1,192
Caldecott Villas, Airbnb and Holiday Homes Under $200
Over 417+ Caldecott Private Villas, Airbnb and Holiday Homes Under $200
New
House
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $198/Night
7 Nights - US $1,386
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
View- Parking
US $124/Night
7 Nights - US $868
Hotel
9.4Exceptional
(1006 Reviews)
1 Bath
- Pool
- Balcony/Terrace
Breakfast- Kitchen
US $134/Night
7 Nights - US $940
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
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
(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
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $195/Night
7 Nights - US $1,362
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
Instantly Bookable Villa Rentals in Caldecott
Over 644+ Instantly Bookable Private Villas in or Near Caldecott
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
(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
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $232/Night
7 Nights - US $1,624
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1538 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $184/Night
7 Nights - US $1,291
Book a Last Minute Place to Stay in Caldecott
About Caldecott Vacation Rentals
Discover over 1401 amazing vacation rental options in Caldecott 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 Caldecott.
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 1002.02 ft², with prices averaging US $303 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 Caldecott.
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Top Pickleball-Ready Accommodation Types in Caldecott
| Type | Count |
|---|---|
| Vacation Homes | 525 |
| Holiday Apartments | 92 |
| Villas | 82 |
| Cottages | 14 |
Use these Quick Filters to Find a Vacation Rental in Caldecott
★ 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 Caldecott with PickleTrip™.
Weather in Caldecott, FL
View the weather forecast for Caldecott before booking your Caldecott 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 Caldecott?
What are the top vacation rentals, resorts, and hotels in Caldecott 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 Caldecott. 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 Caldecott!
- New Updates Lely Resort, 3 bed, golf course home Includes Players Club and Spa
- Lovely 2-Bedroom + Den Condo in Greenlinks Resort
- Generously sized updated lanai showcasing a prime mid-water south view.
- PLAYERS CLUB AVAILABLE, Professionally Renovated, 3 Bedroom Golf Condo
- Welcome to your luxury vacation retreat in the prestigious Majors at Lely Resort
- NEW Luxury 3 BR Greenlinks Condo totally remodeled! Sleeps 8!
- Luxury Golf Villa in Beautiful Lely Resort w/Pool
- 🌞 WOW! FIVE STAR Stunning Retreat! ~ Lely Resort ~ Golf ~ FREE Players Club!🌴
- GOLF, PICKLEBALL, BEACHES, MARCO ISLAND, HAPPY HOUR. this location has it all
- Stunning Flamingo Condo at Lely Resort-Golf/Pool/Courts/Gym
How many pickleball-ready properties have private pools in Caldecott?
Discover 265 accommodations with private or nearby pickleball courts in Caldecott. Some of the best destinations to stay and play pickleball are:
- Water view condo w/access to community amenities, wifi, & outdoor private patio
- Gated Community/Lazy River/Pool/Tennis/Granite/Tile/Lanai with Kitchen
- Updated condo with large lanai + outdoor kitchen. Water view at Magnolia Falls.
- Townhouse in South Naples, Lely resort OLE
Which vacation rentals, resorts, or hotels in Caldecott is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Caldecott? 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+
- 7940 # 626, Naples, FL
- 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 Caldecott?
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 1401 properties listed in Caldecott 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 |
|---|---|
| Calumet Reserve Vacation Rentals in Naples, Florida | 1315 |
| Alden Woods Vacation Rentals in Naples, Florida | 1280 |
People Also Ask
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