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  • Sawgrass Grove Relaxing Retreat
    From $159 per night (USD)

    VRBO

    Sawgrass Grove Relaxing Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy vibrant Sawgrass Grove! Dance to free nightly live music at the Boxcar Stage, savor diverse dining at The Market, ...

    From $159 per night (USD)

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    Details
  • Enchanting 10BR w Themes|Windsor Cay near Disney
    From $470 per night (USD)

    Expedia

    Enchanting 10BR w Themes|Windsor Cay near Disney

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    21

    Summary: Welcome to your Ultimate Orlando Getaway! Discover unmatched luxury and enchantment at this stunning, newly-ren ...

    From $470 per night (USD)

    Expedia

    Details
  • 1149 Spacious Family 5-Bedroom Townhome
    From $285 per night (USD)

    VRBO

    1149 Spacious Family 5-Bedroom Townhome

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Summary: Discover your dream family getaway at 1149 Blue Island Drive, a stunning 5-bedroom townhouse in Clermont, Flori ...

    From $285 per night (USD)

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    Details
  • FOUND IT! Perfect 10BR Family Home – 16356
    From $515 per night (USD)

    Expedia

    FOUND IT! Perfect 10BR Family Home – 16356

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    24

    ✨ **Stunning 10-Bedroom Home in Windsor Cay Resort – Clermont, Florida!** ✨ Welcome to this **incredible 10-bedroom, 8- ...

    From $515 per night (USD)

    Expedia

    Details
  • Luxury 8BR Pool Home at Windsor Cay Resort | Near Disney
    From $834 per night (USD)

    VRBO

    Luxury 8BR Pool Home at Windsor Cay Resort | Near Disney

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    20

    Luxurious 8-Bedroom Retreat at Windsor Cay Resort – Minutes from Disney! Escape to the ultimate vacation haven at Wind ...

    From $834 per night (USD)

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    Details
  • Lovely 5 Bed Pool Townhome Themed Rooms-1296BPW
    From $353 per night (USD)

    Expedia

    Lovely 5 Bed Pool Townhome Themed Rooms-1296BPW

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    11

    Windsor Cay Resort - Clermont, Florida is a beautiful, family-friendly resort community in a prime location. Just a shor ...

    From $353 per night (USD)

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    Details
  • 5 Bedrooms / 5 Bathrooms / Windsor Cay (1137BI)
    From $325 per night (USD)

    VRBO

    5 Bedrooms / 5 Bathrooms / Windsor Cay (1137BI)

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    • Community: Windsor Cay • 5 Bedrooms/ 4.5 Bathrooms/ Sleeps 12 • Disney World® (8.1 miles) SeaWorld (18.3 miles) • Con ...

    From $325 per night (USD)

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    Details
  • Relaxing 5 Bed Pool Townhome Themed Rooms-1280BPW
    From $310 per night (USD)

    Expedia

    Relaxing 5 Bed Pool Townhome Themed Rooms-1280BPW

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Windsor Cay Resort - Clermont, Florida is a beautiful, family-friendly resort community in a prime location. Just a shor ...

    From $310 per night (USD)

    Expedia

    Details
  • Hilltop Golf Course Cottage in The Villages!
    From $145 per night (USD)

    VRBO

    Hilltop Golf Course Cottage in The Villages!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    1/2 Mi to Community Pool & Rec Center | Close to UF Health | Lounge & Dine w/ Views of the 8th Green Nestled in the hea ...

    From $145 per night (USD)

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    Details
  • LOOK! 5BR Pool Home w/Game Room – 1141
    From $319 per night (USD)

    Expedia

    LOOK! 5BR Pool Home w/Game Room – 1141

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    **Spacious 5-Bedroom Townhouse with Private Pool & Themed Rooms – Windsor Cay Resort, Clermont FL** Welcome to your dre ...

    From $319 per night (USD)

    Expedia

    Details
  • 10 Bedrooms / 8 Bathrooms / Windsor Cay (15977CC)
    From $633 per night (USD)

    VRBO

    10 Bedrooms / 8 Bathrooms / Windsor Cay (15977CC)

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    24

    • Community: Windsor Cay • 10 Bedrooms/ 8 Bathrooms/ Sleeps 24 • Disney (8.2 miles) SeaWorld (18.5 miles) Legoland (31.0 ...

    From $633 per night (USD)

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    Details
  • Charming home w/spacious kitchen, water view, enclosed lanai, & Pet Friendly
    From $192 per night (USD)

    Expedia

    Charming home w/spacious kitchen, water view, enclosed lanai, & Pet Friendly

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Please note Winter arrivals are as follows: January 2 - 30 February 1 - 28 March 2 - 30 Welcome to your perfect retreat ...

    From $192 per night (USD)

    Expedia

    Details
  • SUPER HOMEY- 8BDR - PS5, ARCADEs, POKER, LOFT
    From $481 per night (USD)

    VRBO

    SUPER HOMEY- 8BDR - PS5, ARCADEs, POKER, LOFT

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    16

    Summary: Windsor Cay Resort has so many amazing features! Located just 9 miles from the gates of Disney World®, the reso ...

    From $481 per night (USD)

    VRBO

    Details
  • Charming Lakefront Apt. Near Disney
    From $109 per night (USD)

    Expedia

    Charming Lakefront Apt. Near Disney

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to our Charming Lakefront Apartment, located in South Clermont, just 20 minutes from Downtown Orlando, Walt Disn ...

    From $109 per night (USD)

    Expedia

    Details
  • Charming Lakefront Cottage Near Disney
    From $106 per night (USD)

    VRBO

    Charming Lakefront Cottage Near Disney

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to our Charming Lakefront Cottage, located in South Clermont, just 20 minutes from Downtown Orlando, Walt Disney ...

    From $106 per night (USD)

    VRBO

    Details
  • Welcome to The Dove at Eastport\nA 3BR/3 FULL BA home in The Villages, Florida
    From $170 per night (USD)

    Expedia

    Welcome to The Dove at Eastport\nA 3BR/3 FULL BA home in The Villages, Florida

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    The Dove at Eastport – A Stylish 3BR/3 FULL BA Designer Home in Waters Edge just minutes from Eastport, Middleton and Br ...

    From $170 per night (USD)

    Expedia

    Details
  • 3-bedroom villa in fantastic Clermont that backs on to a Conservation Area
    From $160 per night (USD)

    VRBO

    3-bedroom villa in fantastic Clermont that backs on to a Conservation Area

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to this welcoming villa in Clermont. This awesome property features 3 bedrooms with a variety of bed sizes to ac ...

    From $160 per night (USD)

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    Details
  • Beautiful home with private pool and space for the whole family
    From $203 per night (USD)

    Expedia

    Beautiful home with private pool and space for the whole family

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Serenity Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $203 per night (USD)

    Expedia

    Details
  • Beautiful home with private pool and space for the whole family
    From $204 per night (USD)

    VRBO

    Beautiful home with private pool and space for the whole family

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Serenity Stay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $204 per night (USD)

    VRBO

    Details
  • Magical 5BR Townhome with Private Pool – Minutes from Disney
    From $204 per night (USD)

    Expedia

    Magical 5BR Townhome with Private Pool – Minutes from Disney

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    11

    Escape to the brand-new Windsor Cay Resort and experience a one-of-a-kind Orlando vacation in this stylish and family-fr ...

    From $204 per night (USD)

    Expedia

    Details
  • Relaxing Stay with Easy Disney Parks Access | 5 Pools & Free Shuttle!
    From $122 per night (USD)

    VRBO

    Relaxing Stay with Easy Disney Parks Access | 5 Pools & Free Shuttle!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stay inside Disney’s Main Gate at this family-friendly resort! Just minutes from both Disney and Universal, you’ll enjoy ...

    From $122 per night (USD)

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    Details
  • 2 Spacious Rooms Near Disney's Animal Kingdom – W/ 5 Pools & Free Shuttle
    From $243 per night (USD)

    VRBO

    2 Spacious Rooms Near Disney's Animal Kingdom – W/ 5 Pools & Free Shuttle

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Stay inside Disney’s Main Gate at this family-friendly resort! Just minutes from both Disney and Universal, you’ll enjoy ...

    From $243 per night (USD)

    VRBO

    Details
  • Orlando's Best: 3 Magical Rooms w/ Free Breakfast, Pools & Theme Park Access
    From $365 per night (USD)

    VRBO

    Orlando's Best: 3 Magical Rooms w/ Free Breakfast, Pools & Theme Park Access

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    Stay inside Disney’s Main Gate at this family-friendly resort! Just minutes from both Disney and Universal, you’ll enjoy ...

    From $365 per night (USD)

    VRBO

    Details
  • 10 BED | 8 BATH Extraordinary Villa w/ Gamesroom & Pool 15985Cape
    From $442 per night (USD)

    Expedia

    10 BED | 8 BATH Extraordinary Villa w/ Gamesroom & Pool 15985Cape

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    24

    • Community: Windsor Cay • Gated Community • 10 Bedrooms/ 8 Bathrooms/ Sleeps Distances : • Walmart (1.2 miles - 5min ...

    From $442 per night (USD)

    Expedia

    Details
  • 5 Bedrooms / 4.5 Bathrooms / Windsor Cay (16033BW)
    From $330 per night (USD)

    VRBO

    5 Bedrooms / 4.5 Bathrooms / Windsor Cay (16033BW)

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    11

    • Community: Windsor Cay • 5 Bedrooms/ 4.5 Bathrooms/ Sleeps 11 • Disney World® (8.1 miles) SeaWorld (18.3 miles) • Conv ...

    From $330 per night (USD)

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    Details
  • Spacious 5-bedroom villa with AC, WiFi in lovely Clermont
    From $199 per night (USD)

    Expedia

    Spacious 5-bedroom villa with AC, WiFi in lovely Clermont

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    This Clermont villa boasts 5 inviting bedrooms, including 3 queen beds. With AC, a washing machine, WiFi, and more, gues ...

    From $199 per night (USD)

    Expedia

    Details
  • Modern 5 beds/ 5 baths Retreat~Pool
    From $248 per night (USD)

    VRBO

    Modern 5 beds/ 5 baths Retreat~Pool

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to the modern 5BR, 5.5Bath family retreat in the prestigious Windsor Cay Resort community ( resort amenities und ...

    From $248 per night (USD)

    VRBO

    Details
  • Pet Friendly Family Home Close to Everything!
    From $190 per night (USD)

    Expedia

    Pet Friendly Family Home Close to Everything!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Come enjoy peaceful setting near everything The Space: Welcome to your peaceful Central Florida retreat in the ...

    From $190 per night (USD)

    Expedia

    Details
  • 3-bedroom Biker's bungalow in brilliant Clermont Close to Downtown
    From $184 per night (USD)

    VRBO

    3-bedroom Biker's bungalow in brilliant Clermont Close to Downtown

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Make yourself at home in this 3-bedroom Clermont retreat. This gorgeous bungalow boasts 1 king bed and 2 queen beds, per ...

    From $184 per night (USD)

    VRBO

    Details
  • Orchid Greens Getaway
    From $109 per night (USD)

    VRBO

    Orchid Greens Getaway

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nestled on a picturesque course in the villages, Orchid Greens is your gateway to a tranquil vacation. This charming ho ...

    From $109 per night (USD)

    VRBO

    Details
  • Deluxe Getaway/ Themed Room & Private Pool
    From $226 per night (USD)

    VRBO

    Deluxe Getaway/ Themed Room & Private Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Be among the first to experience the excitement of the new Epic Universe park this May 22nd — book your stay wi ...

    From $226 per night (USD)

    VRBO

    Details
  • 10 Bedrooms / 8 Bathrooms / Windsor Cay (15953CC)
    From $629 per night (USD)

    Expedia

    10 Bedrooms / 8 Bathrooms / Windsor Cay (15953CC)

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    22

    • Community: Windsor Cay • 10 Bedrooms/ 8 Bathrooms/ Sleeps 24 • Disney (8.2 miles) SeaWorld (18.5 miles) Legoland (31.0 ...

    From $629 per night (USD)

    Expedia

    Details
  • 9 Mi to Disney World: Family Home w/ Private Pool!
    From $195 per night (USD)

    VRBO

    9 Mi to Disney World: Family Home w/ Private Pool!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Pet Friendly w/ Fee | BBQ Ready | Near Golf Courses Get ready to soak up the Florida sun at this 4-bedroom, 2-bath vaca ...

    From $195 per night (USD)

    VRBO

    Details
  • Golf & Pool Access: Home w/ Yard in Lady Lake
    From $156 per night (USD)

    Expedia

    Golf & Pool Access: Home w/ Yard in Lady Lake

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Dog Friendly w/ Fee | Get Around on the Golf Cart | Home Office Enjoy the fun-filled atmosphere of The Villages from th ...

    From $156 per night (USD)

    Expedia

    Details
  • New 5BR • 15 Mins to Disney • Private Pool
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    VRBO

    New 5BR • 15 Mins to Disney • Private Pool

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to your dream getaway at the beautiful Windsor Cay Resort, the newest gem near Orlando’s top attractions, shoppi ...

    Click For Pricing

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    Details
  • Charming studio in superb Clermont with AC, WiFi
    From $181 per night (USD)

    Expedia

    Charming studio in superb Clermont with AC, WiFi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Your Clermont getaway starts at this welcoming studio. This peaceful retreat offers heating, AC, and WiFi for guests to ...

    From $181 per night (USD)

    Expedia

    Details
  • 10 BED | 8 BATH Ultimate Luxury Villa Gamesroom & Pool 16248Saint
    From $405 per night (USD)

    VRBO

    10 BED | 8 BATH Ultimate Luxury Villa Gamesroom & Pool 16248Saint

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    24

    • Community: Windsor Cay • Gated Community • 10 Bedrooms/ 8 Bathrooms/ Sleeps 26 Distances : • Walmart (1.2 miles - 5mi ...

    From $405 per night (USD)

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    Details
  • Indulge in Luxury | Secret Hideaway in Clermont
    From $246 per night (USD)

    Expedia

    Indulge in Luxury | Secret Hideaway in Clermont

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    This fully furnished, newly renovated 5-bedroom home in Clermont won't last long! Whether you're looking for a dream hom ...

    From $246 per night (USD)

    Expedia

    Details
  • 5-Bedroom – Private Pool – 15min to Disney - Brand New House - Summer Kitchen
    From $294 per night (USD)

    VRBO

    5-Bedroom – Private Pool – 15min to Disney - Brand New House - Summer Kitchen

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    <p>Located in Four Corners, this welcoming vacation home brings it all within your reach. With convenient onsite parking ...

    From $294 per night (USD)

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    Details
  • Spacious 5-bedroom townhome with  AC amazing  windsor cay new resort   Clermont
    From $352 per night (USD)

    Expedia

    Spacious 5-bedroom townhome with AC amazing windsor cay new resort Clermont

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    14

    Escape to this enchanting townhome in picturesque Clermont. This 5-bedroom retreat offers a king bed, queen bed, and two ...

    From $352 per night (USD)

    Expedia

    Details
  • Charming 4-bedroom villa with WiFi and AC in tranquil Clermont near to Disney
    From $190 per night (USD)

    VRBO

    Charming 4-bedroom villa with WiFi and AC in tranquil Clermont near to Disney

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Located in Clermont, enjoy what this 4-bedroom villa has to offer. Marvelous views and tranquil surroundings await guest ...

    From $190 per night (USD)

    VRBO

    Details
  • Utimate 7BR villa w/Game Loft | WCR near Disney
    From $392 per night (USD)

    Expedia

    Utimate 7BR villa w/Game Loft | WCR near Disney

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    15

    Summary: Unwind in style at this brand-new 7-bedroom, 6-bathroom luxury villa in the highly desirable Windsor Cay Resort ...

    From $392 per night (USD)

    Expedia

    Details
  • 2 Mi to Dtwn: Mt Dora Home w/ Grill!
    From $135 per night (USD)

    VRBO

    2 Mi to Dtwn: Mt Dora Home w/ Grill!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Peaceful Surroundings | Great For Pondside Bird-Watching | 5 Mi to Lake Eustis Your Mt Dora getaway begins at this 2-be ...

    From $135 per night (USD)

    VRBO

    Details
  • Hot Tub: Home, 2 Mi to Dtwn Mt Dora!
    From $193 per night (USD)

    Expedia

    Hot Tub: Home, 2 Mi to Dtwn Mt Dora!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Shared Outdoor Space | Great For Pondside Bird-Watching | BBQ Ready Feel the pulse of Florida's 'Festival City' from t ...

    From $193 per night (USD)

    Expedia

    Details
  • Spacious lake view home near Historic Downtown Mount Dora!
    From $214 per night (USD)

    VRBO

    Spacious lake view home near Historic Downtown Mount Dora!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to your home away from home, a cozy and inviting 3-bedroom, 2-bath lakeview gem nestled in the serene beauty of ...

    From $214 per night (USD)

    VRBO

    Details
  • 18 Mi to Disney: Clermont Home w/ Yard
    From $228 per night (USD)

    Expedia

    18 Mi to Disney: Clermont Home w/ Yard

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Close to Shopping & Restaurants | Family Friendly | Modern Interior Slide into your flip-flops and let the good times r ...

    From $228 per night (USD)

    Expedia

    Details
  • Pet-Friendly Home w/ Golf Cart in The Villages!
    From $139 per night (USD)

    VRBO

    Pet-Friendly Home w/ Golf Cart in The Villages!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Snowbirds Welcome | Near Shopping & Dining Embrace the laid-back Florida lifestyle at this peaceful Lady Lake vacation ...

    From $139 per night (USD)

    VRBO

    Details
  • Luxury Themed Brand New 01/2025 Pvt Pool-Near Disney-Windsor Cay Resort
    From $234 per night (USD)

    Expedia

    Luxury Themed Brand New 01/2025 Pvt Pool-Near Disney-Windsor Cay Resort

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    ★ Ensuring the safety and hygiene of our guests is our utmost priority. Rest assured that our property undergoes thoroug ...

    From $234 per night (USD)

    Expedia

    Details
  • NEW House - 4 bed / Private pool
    From $220 per night (USD)

    VRBO

    NEW House - 4 bed / Private pool

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This cozy and beautiful four-bedroom house has a spacious living area and a fully equipped kitchen. It also includes a b ...

    From $220 per night (USD)

    VRBO

    Details
  • Family Villa w/ Pool + Foosball + Loft Lounge | 17 Min to Disney
    From $151 per night (USD)

    Expedia

    Family Villa w/ Pool + Foosball + Loft Lounge | 17 Min to Disney

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Contact us for monthly specials (up to 3 months)! Welcome to your perfect getaway near Disney and all major other attra ...

    From $151 per night (USD)

    Expedia

    Details
  • Impressive Hideaway with Private pool and Near Parks
    From $280 per night (USD)

    VRBO

    Impressive Hideaway with Private pool and Near Parks

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Summary: No Shared Rooms No Resort Fees in Included Resort Amenities Private pool Stay 30 nights, get $200 credit for ex ...

    From $280 per night (USD)

    VRBO

    Details
  • Spacious and charming private Pool Townhome. Nxt to Disney
    From $191 per night (USD)

    Expedia

    Spacious and charming private Pool Townhome. Nxt to Disney

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This Townhome boasts 4 inviting bedrooms, including 1 king bed, 2 queen beds, and 1 twin bed. With 3 bathrooms featuring ...

    From $191 per night (USD)

    Expedia

    Details
  • 5 Bedrooms / 4.5 Bathrooms / Windsor Cay (16053BW)
    From $515 per night (USD)

    VRBO

    5 Bedrooms / 4.5 Bathrooms / Windsor Cay (16053BW)

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    • Community: Windsor Cay • 5 Bedrooms/ 4.5 Bathrooms/ Sleeps 10 • Disney World® (8.1 miles) SeaWorld (18.3 miles) • Conv ...

    From $515 per night (USD)

    VRBO

    Details
  • 6 bed near Disney, with conservation views and sun all day on extended deck
    From $286 per night (USD)

    Expedia

    6 bed near Disney, with conservation views and sun all day on extended deck

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    12

    Welcome Step in, kick off your shoes and relax! This beautifully appointed 6 bedroom villa offers over 2,200 sq ft of sp ...

    From $286 per night (USD)

    Expedia

    Details
  • 4-bedroom house- Black Sheep Hideaway: Modern Countryside Serenity
    From $410 per night (USD)

    VRBO

    4-bedroom house- Black Sheep Hideaway: Modern Countryside Serenity

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Your Clermont adventure begins at this delightful 4-bedroom house. With 3 queen beds and 1 twin bed, this lovely propert ...

    From $410 per night (USD)

    VRBO

    Details
  • Resort-Like Escape  BBQ, Pizza Oven & Pickleball
    From $122 per night (USD)

    Expedia

    Resort-Like Escape BBQ, Pizza Oven & Pickleball

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unfurnished condo w/ air bed, Wi-Fi & peaceful vibes Enjoy pickleball courts, a sparkling pool, outdoor fire pit, BBQ l ...

    From $122 per night (USD)

    Expedia

    Details
  • 3BR Pool Home + Bonus Lounge w/ Daybed • WiFi • Sleeps 10
    From $208 per night (USD)

    VRBO

    3BR Pool Home + Bonus Lounge w/ Daybed • WiFi • Sleeps 10

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Your cozy getaway awaits in Clermont at this fabulous townhome. With 3 bedrooms including 1 king bed and 2 full beds, al ...

    From $208 per night (USD)

    VRBO

    Details
  • Charming 4-bedroom house in Leesburg Florida!
    From $235 per night (USD)

    Expedia

    Charming 4-bedroom house in Leesburg Florida!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Get ready to relax in this 4-bedroom house in Leesburg. This quaint property features 1 king bed and 3 queen beds, perfe ...

    From $235 per night (USD)

    Expedia

    Details
  • 10 Bedrooms / 8 Bathrooms / Windsor Cay (15945CC)
    From $607 per night (USD)

    VRBO

    10 Bedrooms / 8 Bathrooms / Windsor Cay (15945CC)

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    22

    • Community: Windsor Cay • 10 Bedrooms/ 8 Bathrooms/ Sleeps 24 • Disney World® (8.2 miles) SeaWorld (18.5 miles) • Conv ...

    From $607 per night (USD)

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    Details
  • 10 Bedrooms / 8 Bathrooms / Windsor Cay (16005CC)
    From $667 per night (USD)

    Expedia

    10 Bedrooms / 8 Bathrooms / Windsor Cay (16005CC)

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    26

    • Community: Windsor Cay • 10 Bedrooms/ 8 Bathrooms/ Sleeps 26 • Disney (8.2 miles) SeaWorld (18.5 miles) Legoland (31.0 ...

    From $667 per night (USD)

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    Details
  • 5 Bedrooms / 4.5 Bathrooms / Windsor Cay (1153BI)
    From $338 per night (USD)

    VRBO

    5 Bedrooms / 4.5 Bathrooms / Windsor Cay (1153BI)

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    • Community: Windsor Cay • 5 Bedrooms/ 4.5 Bathrooms/ Sleeps 12 • Disney (8.1 miles) SeaWorld (18.3 miles) Legoland (29. ...

    From $338 per night (USD)

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    Details
  • Fabulous lakefront villa 4 bedrooms with pool, spa, fitness room, ping-pong ...
    From $359 per night (USD)

    Expedia

    Fabulous lakefront villa 4 bedrooms with pool, spa, fitness room, ping-pong ...

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Stunning lakefront retreat, where modern luxury meets natural beauty. Spacious and stylish home offers panoramic west-fa ...

    From $359 per night (USD)

    Expedia

    Details
  • Charming lakefront 3BR 3BA house w/ EV chg in heart of Mt. Dora. Nature abounds.
    From $274 per night (USD)

    VRBO

    Charming lakefront 3BR 3BA house w/ EV chg in heart of Mt. Dora. Nature abounds.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Escape to the tranquility of our pet-friendly Lakehouse. It is a lakefront 3-bedroom, 3-bathroom house surrounded by n ...

    From $274 per night (USD)

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    Details
  • Tuscan Style Villa / Near Disney
    From $152 per night (USD)

    Expedia

    Tuscan Style Villa / Near Disney

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Welcome to Your Tuscan-Inspired Disney Retreat! This cozy, family-friendly villa is nestled in a gated resort just minut ...

    From $152 per night (USD)

    Expedia

    Details
  • Fabulous 10 Bed Pool Home with Game Room-16248SMS
    From $720 per night (USD)

    VRBO

    Fabulous 10 Bed Pool Home with Game Room-16248SMS

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    24

    Windsor Cay Resort - Clermont, Florida is a beautiful, family-friendly resort community in a prime location. Just a shor ...

    From $720 per night (USD)

    VRBO

    Details
  • 2025 Brand NEW 05Bdrms At Windsor Cay
    From $239 per night (USD)

    Expedia

    2025 Brand NEW 05Bdrms At Windsor Cay

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    11

    * Bedrooms: 5 * Bathrooms: 5 * Accommodates: 10 * Property type: Townhome * Location: Windsor Cay Resort 1st Floor Bedr ...

    From $239 per night (USD)

    Expedia

    Details
  • This single family home offers everything you need for the perfect vacation!
    From $207 per night (USD)

    VRBO

    This single family home offers everything you need for the perfect vacation!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This luxury single family home offers everything you need for the perfect Disney Family vacation! We have 2,000+ SQFT of ...

    From $207 per night (USD)

    VRBO

    Details
  • Charming 2-bedroom villa in brilliant The Villages with WiFi, AC
    From $134 per night (USD)

    Expedia

    Charming 2-bedroom villa in brilliant The Villages with WiFi, AC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Charming, Cozy, fully furnished Patio Villa in the Village of Waters Edge. Waters Edge is close to both Eastport and Mid ...

    From $134 per night (USD)

    Expedia

    Details
  • 10BR Villa w/ Pool + Themed Rooms Near Disney
    From $590 per night (USD)

    VRBO

    10BR Villa w/ Pool + Themed Rooms Near Disney

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    28

    About this space Welcome to your ultimate group getaway! This stunning 10-bedroom home is the perfect choice for large f ...

    From $590 per night (USD)

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    Details
  • Charming 2-Bedroom, 2-Bath Villa in Newell Village
    From $175 per night (USD)

    Expedia

    Charming 2-Bedroom, 2-Bath Villa in Newell Village

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the perfect blend of comfort, convenience, and entertainment in this beautiful 2-bedroom, 2-bath villa, newly b ...

    From $175 per night (USD)

    Expedia

    Details
  • 10 Bedrooms / 8 Bathrooms / Windsor Cay (15973CC)
    From $615 per night (USD)

    VRBO

    10 Bedrooms / 8 Bathrooms / Windsor Cay (15973CC)

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    22

    • Community: Windsor Cay • 10 Bedrooms/ 8 Bathrooms/ Sleeps 28 • Disney World® (8.3 miles) SeaWorld (18.5 miles) • Conv ...

    From $615 per night (USD)

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    Details
  • Luxurious Windsor Cay Villa | Private Pool, Epic Game Room & Minutes to Disney!
    From $380 per night (USD)

    VRBO

    Luxurious Windsor Cay Villa | Private Pool, Epic Game Room & Minutes to Disney!

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Dive into the magic of Orlando from this stunning 5-bedroom paradise! Relax poolside in your private oasis, challenge fa ...

    From $380 per night (USD)

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    Details
  • Come stay at this wonderful vacation home for a relaxing stay!
    From $531 per night (USD)

    VRBO

    Come stay at this wonderful vacation home for a relaxing stay!

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    21

    Guests have keyless access to the entire house using the digital lock with a keypad on the front door as well as private ...

    From $531 per night (USD)

    VRBO

    Details
  • Windsor Cay 5bd with pool
    From $255 per night (USD)

    Expedia

    Windsor Cay 5bd with pool

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    This amazing townhome with 5 Bedroom 4.5 Bathroom, 2,271 Sq.Ft. home with private splash pool is perfectly located, just ...

    From $255 per night (USD)

    Expedia

    Details
  • 10 Bedrooms / 8 Bathrooms / Windsor Cay (15965CC)
    From $645 per night (USD)

    VRBO

    10 Bedrooms / 8 Bathrooms / Windsor Cay (15965CC)

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    28

    • Community: Windsor Cay • 10 Bedrooms/ 8 Bathrooms/ Sleeps 28 • Disney (8.2 miles) SeaWorld (18.5 miles) Legoland (31.0 ...

    From $645 per night (USD)

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    Details
  • \The Skinny\ on Lake Gertrude! B2G1 night free in July!
    From $428 per night (USD)

    Expedia

    \"The Skinny\" on Lake Gertrude! B2G1 night free in July!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Lakefront Vacation Getaway on Lake Gertrude – Mount Dora, FL 3 Bedrooms | 2.5 Bathrooms. ...

    From $428 per night (USD)

    Expedia

    Details
  • Beautiful home with private pool and space for the whole family
    From $267 per night (USD)

    VRBO

    Beautiful home with private pool and space for the whole family

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    16

    Palm Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...

    From $267 per night (USD)

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    Details
  • Sunny open-layout retreat with modern flair and pet-friendly charm
    From $121 per night (USD)

    Expedia

    Sunny open-layout retreat with modern flair and pet-friendly charm

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Please note Winter arrivals are as follows: January 2 - 30 February 1 - 28 March 2 - 30 Welcome to your next Florida re ...

    From $121 per night (USD)

    Expedia

    Details
  • Luxury new Pool Home! 10 min from Disney - WALK to NEW WATER PARK!
    From $331 per night (USD)

    VRBO

    Luxury new Pool Home! 10 min from Disney - WALK to NEW WATER PARK!

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    Prepare to be amazed! This BRAND NEW elegantly furnished storybook resort home with 5 full ensuites is the absolute vaca ...

    From $331 per night (USD)

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    Details
  • 2025 Brand NEW 06 Bedrooms At Windsor Cay
    From $463 per night (USD)

    Expedia

    2025 Brand NEW 06 Bedrooms At Windsor Cay

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    16

    - Resort Amenities: * The amenities at resort are still under development but you will have full access to the amazing f ...

    From $463 per night (USD)

    Expedia

    Details
  • Stunning 8BR Pool Gameroom Minutes to Disney
    From $437 per night (USD)

    VRBO

    Stunning 8BR Pool Gameroom Minutes to Disney

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    18

    This amazing house with 8 Bedroom 6 Bathroom, 4,034 Sq.Ft. home with private splash pool is perfectly located, just minu ...

    From $437 per night (USD)

    VRBO

    Details
  • Lakeview Designer Home in Valle Verde Village
    From $219 per night (USD)

    Expedia

    Lakeview Designer Home in Valle Verde Village

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy comfort, convenience, and sustainability in our spacious, custom-designed solar home, ideally located with peacefu ...

    From $219 per night (USD)

    Expedia

    Details
  • Family Friendly w Pool near Disney @ Orlando 1420
    From $197 per night (USD)

    VRBO

    Family Friendly w Pool near Disney @ Orlando 1420

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Summary: This 2-story townhouse is perfect for families—offering the comfort of home and the perks of resort living! Sle ...

    From $197 per night (USD)

    VRBO

    Details
  • 3 Bedroom 2.5 Bathroom Clear Creek 1050
    From $152 per night (USD)

    Expedia

    3 Bedroom 2.5 Bathroom Clear Creek 1050

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    NEW LISTING! NEW FLOORING - NO CARPET AT ALL SINGLE LEVEL HOME with private HEATED pool! Located in the quiet commu ...

    From $152 per night (USD)

    Expedia

    Details
  • COSY POOlL HOME NEAR DISNEY AND OUTLETS
    From $192 per night (USD)

    VRBO

    COSY POOlL HOME NEAR DISNEY AND OUTLETS

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    <p>Located in Four Corners, this welcoming property brings it all within your reach. With convenient onsite parking, you ...

    From $192 per night (USD)

    VRBO

    Details
  • Warlock Retreat - Private Pool
    From $377 per night (USD)

    Expedia

    Warlock Retreat - Private Pool

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to Warlock Retreat! Step into a world of enchantment with our 5-bedroom fantasy-themed family vacation rental, l ...

    From $377 per night (USD)

    Expedia

    Details
  • Top Stunning Minions DLuxx  Home  Windsor Cay 1185
    From $244 per night (USD)

    VRBO

    Top Stunning Minions DLuxx Home Windsor Cay 1185

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to our brand new 5-bedroom, 4-bathroom townhome located in the beautiful Windsor Cay Resort. Be one of the first ...

    From $244 per night (USD)

    VRBO

    Details
  • 2025 Brand NEW 05 Bedrooms At Windsor Cay
    From $315 per night (USD)

    Expedia

    2025 Brand NEW 05 Bedrooms At Windsor Cay

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    *The Space * Accommodates: 12 * Bathrooms: 5 * Bedrooms: 4.5 * Property type: Luxury Villa * Location: Windsor Cay - R ...

    From $315 per night (USD)

    Expedia

    Details
  • Ref 113. Modern family villa, own private pool, near Disney.
    From $198 per night (USD)

    VRBO

    Ref 113. Modern family villa, own private pool, near Disney.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to our superb 5-bedroom 4-bathroom villa, located in the community of Silver Creek in Clemont, just off Highway ...

    From $198 per night (USD)

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    Details
  • 2025 Brand NEW 05 Bedrooms At Windsor Cay
    From $299 per night (USD)

    Expedia

    2025 Brand NEW 05 Bedrooms At Windsor Cay

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    The Space •⁠ ⁠Accommodates: 14 •⁠ ⁠Bedrooms: 5 •⁠ ⁠Bathrooms: 4 •⁠ ⁠Property type: Luxury Villa •⁠ ⁠Location: Wi ...

    From $299 per night (USD)

    Expedia

    Details
  • 561f) Very large 2 bedroom with King Bed!
    From $168 per night (USD)

    VRBO

    561f) Very large 2 bedroom with King Bed!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located just minutes from Southern Oaks, Jubilee, Mickylee, and Championship golf courses, this 2-bedroom home offers ea ...

    From $168 per night (USD)

    VRBO

    Details
  • Cozy Camper Stay in Mount Dora – Pet Friendly, Walk to Downtown!
    From $115 per night (USD)

    Expedia

    Cozy Camper Stay in Mount Dora – Pet Friendly, Walk to Downtown!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Looking for a unique Mount Dora experience? Stay in our permanently set-up camper — perfect for a cozy getaway for two — ...

    From $115 per night (USD)

    Expedia

    Details
  • NEW!! Sunsets at Cherry Lake-2 bedroom lake front cottage
    From $206 per night (USD)

    VRBO

    NEW!! Sunsets at Cherry Lake-2 bedroom lake front cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This gorgeous cottage in Groveland is the perfect home base for your trip. With 2 bedrooms including a king bed, queen b ...

    From $206 per night (USD)

    VRBO

    Details
  • Lake Haven Retreat, Private Dock & Peaceful Views
    From $226 per night (USD)

    VRBO

    Lake Haven Retreat, Private Dock & Peaceful Views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Escape to tranquility at Lake Haven Retreat — a serene lakefront home nestled in the heart of Tavares. This spa ...

    From $226 per night (USD)

    VRBO

    Details
  •  2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access
    From $186 per night (USD)

    VRBO

    2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to our cozy 2BR/2BA lake-themed cottage in Clermont—just 20 mins from Disney, Universal & more! Unwind by the hea ...

    From $186 per night (USD)

    VRBO

    Details
  • 3-bedroom house with Pool and Spa in The Villages with great views and privacy.
    From $353 per night (USD)

    VRBO

    3-bedroom house with Pool and Spa in The Villages with great views and privacy.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Experience The Villages like a local in this 3-bedroom, 2 bath house - with a master! Fully furnished and complete with ...

    From $353 per night (USD)

    VRBO

    Details
  • Casa Del Toro at Spanish Springs (Del Mar)
    From $127 per night (USD)

    VRBO

    Casa Del Toro at Spanish Springs (Del Mar)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Casa Del Toro at Spanish Springs Charming 2-Bedroom Retreat with Bonus Trundle Bed – Pet Friendly! Welcome to Casa Del ...

    From $127 per night (USD)

    VRBO

    Details
  • Playful Villa Ophelia (Lake Denham)
    From $138 per night (USD)

    VRBO

    Playful Villa Ophelia (Lake Denham)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    🌴 Villa Ophelia – Playful Patio Escape at Lake Denham! 🌞 2 Bed | 2 Bath | Spacious Lanai | Dog Friendly (with Approval ...

    From $138 per night (USD)

    VRBO

    Details
  • The Launch Pad - House with boat ramp on corner deep water canal lot
    From $278 per night (USD)

    VRBO

    The Launch Pad - House with boat ramp on corner deep water canal lot

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Bring your boats/watercrafts and launch directly from the property!  This property has a private 13 feet wide commercial ...

    From $278 per night (USD)

    VRBO

    Details
  • Summer Bay Resort 2br suite, Saturday check-in
    From $98 per night (USD)

    Expedia

    Summer Bay Resort 2br suite, Saturday check-in

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    This offer is only valid in 7 Night Intervals on a Saturday to Saturday schedule. All other offers cannot be accommodate ...

    From $98 per night (USD)

    Expedia

    Details