Trip The Film - Vacation Rentals in Water Oak Country Club Estates

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From US $138

         

10.0 (77 Reviews)

Villa

VILLA 2 MASTER SUITES & 2 GOLF CARTS

• Air Conditioner
• Parking
• Pet Friendly

• Leesburg
• The Villages

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From US $65

         

9.1 (35 Reviews)

House

Village Of Country Club Hills COUPLES ONLY

• Air Conditioner
• Parking
• Pool

• Leesburg
• The Villages

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From US $259

         

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9.6 (8 Reviews)

Cottage

Grand Oaks Resort

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Weirsdale

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From US $606

         

10.0 (60 Reviews)

House

Perfect for FAMILY REUNIONS. Close by The Villages & shopping yet very private.

• Air Conditioner
• Parking
• Pet Friendly

• Leesburg
• Lady Lake

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From US $212

         

New

House

Across from pool! Centrally Located!

• Air Conditioner
• Parking
• Child Friendly

• Leesburg
• Del Mar

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From US $321

         

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New

Cottage

Renovated Villa Btwn Lake Sumter & Spanish Springs

• Air Conditioner
• Pool
• TV

• Leesburg
• Lady Lake

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From US $204

         

8.0 (16 Reviews)

House

One Of A Kind Dog Villa close to Lake Sumter Landing w/Golf Cart, & WiFi!

• Air Conditioner
• Pet Friendly
• Pool

• Leesburg
• Mallory Square

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From US $167

         

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10.0 (6 Reviews)

House

Peaceful Lady Lake Home with Screened-In Porch!

• Parking
• Accessibility
• Transportation/Shuttle

• Leesburg
• Del Mar

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From US $200

         

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New

Cottage

Lady Lake House w/Lanai & Community Pool!

• Air Conditioner
• Parking
• Pool

• Leesburg
• The Villages

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From US $163

         

10.0 (14 Reviews)

House

Lovely Lady Lake Home w/Resort Amenities & Lanai!

• Air Conditioner
• Parking
• Pool

• Leesburg
• The Villages

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From US $191

         

9.6 (68 Reviews)

House

Walk to Spanish Springs, free 4 seater golf cart, covered patio! Pools nearby!

• Air Conditioner
• Parking
• Pool

• Leesburg
• The Villages

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From US $160

         

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10.0 (1 Review)

Villa

Score big in this hoops-themed retreat packed with college basketball pride!

• Air Conditioner
• Pool
• TV

• Leesburg
• Lady Lake

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From US $199

         

10.0 (128 Reviews)

House

Entire 3 Bedroom Home in The Villages - Sleeps 10

• Air Conditioner
• Parking
• Pool

• Leesburg
• Del Mar

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From US $314

         

10.0 (99 Reviews)

House

Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI

• Air Conditioner
• Parking
• Pool

• Leesburg
• The Villages

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From US $114

         

10.0 (67 Reviews)

House

Marilyn’s Romantic Getaway

• Air Conditioner
• Parking
• Pool

• Leesburg
• Lady Lake

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From US $109

         

10.0 (48 Reviews)

House

Cozy Villages villa, 2 bed, 2 bath. Great Location

• Air Conditioner
• Parking
• Pet Friendly

• Leesburg
• The Villages

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From US $216

         

10.0 (44 Reviews)

House

Beautifully updated and close to everything! Yamaha gas cart included!

• Air Conditioner
• Parking
• Pet Friendly

• Leesburg
• The Villages

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From US $284

         

10.0 (42 Reviews)

House

Special OFFER Limited time The Villages January 2026 availability + golf cart

• Air Conditioner
• Parking
• Pet Friendly

• Leesburg
• Mallory Square

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From US $208

         

10.0 (34 Reviews)

House

Peaceful Lady Lake Home w/Screened-In Porch!

• Air Conditioner
• Parking
• Pool

• Leesburg
• Del Mar

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From US $166

         

10.0 (32 Reviews)

House

2 bedrm, den, 2 living rms, 2 baths, near Spanish Springs, golf cart included,

• Air Conditioner
• Parking
• Pool

• Leesburg
• The Villages

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From US $468

         

10.0 (29 Reviews)

House

Private Heated Pool and Hottub , Pet Friendly, New Golf Cart , Close to shopping

• Air Conditioner
• Parking
• Pet Friendly

• Leesburg
• The Villages

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From US $119

         

10.0 (22 Reviews)

House

Best location, dog friendly, and gas golf cart included!

• Air Conditioner
• Pet Friendly
• Pool

• Leesburg
• The Villages

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From US $238

         

10.0 (19 Reviews)

House

Villa Tortuga Modern Updated home with 2beds/2bath Modern Farmhouse w/Golfcartn

• Air Conditioner
• Parking
• Pool

• Leesburg
• The Villages

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From US $309

         

10.0 (17 Reviews)

House

Rare find in Historic Orange Blossom 3/2 with golf cart

• Air Conditioner
• Pet Friendly
• Security/Safety

• Leesburg
• The Villages

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★ Pro Tip: Tripthefilm makes it easy to compare the best listings on Tripthefilm homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Tripthefilm homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Water Oak Country Club Estates.