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Vacation rentals in Kissimmee, Florida, United States

Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park

1 bedroom·1 bath

Orlando • Florida

452,38 $ USD gesamt für 3 Nächte

25.–28. Sept. 2026

Exterior of this lovely home with driveway for two vehicles

Formal living area at the entrance to the home with stylish seating - a great spot for reading, relaxing and chatting

Stylish open-plan living space with Smart TV, ceiling fan and sliding doors to the pool deck

Private pool with spa (pool/spa heat is an optional pre-bookable extra). There is also a pool safety fence.

The garage has been converted into a games room with air hockey and table football

Great 5 Bed Pool Home, Games Room, Disney 9 miles!

5 bedrooms·3 baths

Clermont • Florida

5(2 reviews)

780,00 $ USD gesamt für 3 Nächte

25.–28. Sept. 2026

Lake Eola Thornton Park Studio with Balcony

Lake Eola Thornton Park Studio with Balcony

Lake Eola Thornton Park Studio with Balcony

Lake Eola Thornton Park Studio with Balcony

Lake Eola Thornton Park Studio with Balcony

Lake Eola Thornton Park Studio with Balcony

0 bedrooms·1 bath

Orlando • Florida

4.93(46 reviews)

381,88 $ USD gesamt für 3 Nächte

27.–30. Sept. 2026

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

1 bedroom·1 bath

Orlando • Florida

5(26 reviews)

364,25 $ USD gesamt für 3 Nächte

27.–30. Sept. 2026

Historic Lake Eola studio Thornton Park

Historic Lake Eola studio Thornton Park

Historic Lake Eola studio Thornton Park

Historic Lake Eola studio Thornton Park

Historic Lake Eola studio Thornton Park

Historic Lake Eola studio Thornton Park

0 bedrooms·1 bath

Orlando • Florida

5(11 reviews)

364,25 $ USD gesamt für 3 Nächte

27.–30. Sept. 2026

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

1 bedroom·1 bath

Orlando • Florida

411,25 $ USD gesamt für 3 Nächte

26.–29. Sept. 2026

3-Bedroom Luxury House

3-Bedroom Luxury House

3-Bedroom Luxury House

3-Bedroom Luxury House

3-Bedroom Luxury House

3-Bedroom Luxury House

4 bedrooms·2 baths

Orlando • Florida

896,65 $ USD gesamt für 3 Nächte

26.–29. Sept. 2026

WC16211 LUXURY BRAND NEW Cozy Pool Townhouse near Disney

5 bedrooms·5½ baths

Clermont • Florida

1.482,05 $ USD gesamt für 4 Nächte

26.–30. Sept. 2026

WC16077 LUXURY BRAND NEW Cozy Pool Townhouse near Disney

5 bedrooms·4½ baths

Clermont • Florida

1.152,70 $ USD gesamt für 4 Nächte

26.–30. Sept. 2026

Private Heat Pool & Hot Tub | Games Room image 1

Private Heat Pool & Hot Tub | Games Room image 2

Private Heat Pool & Hot Tub | Games Room image 3

Private Heat Pool & Hot Tub | Games Room image 5

Private Heat Pool & Hot Tub | Games Room image 6

Private Heat Pool & Hot Tub | Games Room

5 bedrooms·4 baths

Clermont • Florida

1.395,27 $ USD gesamt für 4 Nächte

26.–30. Sept. 2026

Cozy Vintage Family Retreat

Cozy Vintage Family Retreat

Cozy Vintage Family Retreat

Cozy Vintage Family Retreat

Cozy Vintage Family Retreat

Cozy Vintage Family Retreat

2 bedrooms·2 baths

Orlando • Florida

1.030,58 $ USD gesamt für 3 Nächte

1.–4. Apr. 2027

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

5 bedrooms·3 baths

Haines City • Florida

3.361,50 $ USD gesamt für 10 Nächte

26. Sept. – 6. Okt. 2026

Stylish & Cozy King Bed Retreat @ Baldwin Park image 1

Stylish & Cozy King Bed Retreat @ Baldwin Park image 2

Stylish & Cozy King Bed Retreat @ Baldwin Park image 3

Stylish & Cozy King Bed Retreat @ Baldwin Park image 4

Stylish & Cozy King Bed Retreat @ Baldwin Park image 5

Stylish & Cozy King Bed Retreat @ Baldwin Park

2 bedrooms·2 baths

Orlando • Florida

5(63 reviews)

596,00 $ USD gesamt für 3 Nächte

26.–29. Sept. 2026

Private Entry 1/1 Apt Full size Kitchen - Welcome!

Private Entry 1/1 Apt Full size Kitchen - Welcome!

Private Entry 1/1 Apt Full size Kitchen - Welcome!

Private Entry 1/1 Apt Full size Kitchen - Welcome!

Private Entry 1/1 Apt Full size Kitchen - Welcome!

Private Entry 1/1 Apt Full size Kitchen - Welcome!

1 bedroom·1 bath

Orlando • Florida

4.91(23 reviews)

$66 – $75/ Nacht(zzgl. Gebühren & Steuern)

Ortona's Best Kept Secret 3/2 Spacious Home

Ortona's Best Kept Secret 3/2 Spacious Home

Ortona's Best Kept Secret 3/2 Spacious Home

Ortona's Best Kept Secret 3/2 Spacious Home

Ortona's Best Kept Secret 3/2 Spacious Home

Ortona's Best Kept Secret 3/2 Spacious Home

3 bedrooms·2 baths

Orlando • Florida

668,63 $ USD gesamt für 3 Nächte

26.–29. Sept. 2026

Modern Family Retreat Near Disney

Modern Family Retreat Near Disney

Modern Family Retreat Near Disney

Modern Family Retreat Near Disney

Modern Family Retreat Near Disney

Modern Family Retreat Near Disney

3 bedrooms·2 baths

Orlando • Florida

646,60 $ USD gesamt für 3 Nächte

26.–29. Sept. 2026

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

3 bedrooms·2 baths

Winter Haven • Florida

733,30 $ USD gesamt für 3 Nächte

1.–4. Okt. 2026

A space made for fun and unforgettable moments: Perfect for games, laughter, and time together

Designed for comfort and shared experiences: A place where good food and great company come together

Relax in Orlando, Florida! This peaceful bedroom features pastel accents, cozy bedding, natural light & a mounted TV—perfect for couples, solo travelers, or long-term guests seeking comfort, style, and a restful retreat near top attractions.

Feel at home in Orlando, Florida! This serene bedroom with soft blue walls, cozy green throw & a cheerful “Together” pillow is perfect for couples, solo travelers, or long-term guests seeking warmth, comfort, and a welcoming retreat.

Unwind in Orlando, Florida! This modern bathroom features marble-style tile, sleek black fixtures, and natural light—perfect for couples, families, or long-term guests seeking comfort, cleanliness, and a touch of contemporary elegance.

Game room fun | Family stays | Near theme parks

3 bedrooms·2 baths

Orlando • Florida

1.203,87 $ USD gesamt für 3 Nächte

3.–6. Okt. 2026

Refresh, reset, and relax: A space that feels as good as it looks.

Fresh spaces, peaceful moments: Where comfort begins and stress fades away.

Fun-filled game room with pool table and bar area – perfect for family entertainment at Oh Winter Heaven, Winter Haven FL

Crystal-clear private pool with sun loungers and lush tropical landscaping – Oh Winter Heaven's resort-style backyard

Open-concept kitchen, dining and game room view – fully equipped for your perfect Florida vacation at Oh Winter Heaven

Private Pool | Game Room Fun | Fenced Yard

4 bedrooms·3 baths

Winter Haven • Florida

999,00 $ USD gesamt für 3 Nächte

26.–29. Sept. 2026

Spacious, family retreat near Orlando attractions

Spacious, family retreat near Orlando attractions

Spacious, family retreat near Orlando attractions

Spacious, family retreat near Orlando attractions

Spacious, family retreat near Orlando attractions

Spacious, family retreat near Orlando attractions

3 bedrooms·2 baths

Clermont • Florida

5(18 reviews)

1.000,13 $ USD gesamt für 4 Nächte

27.–31. Okt. 2026

Cute & Cozy in Winter Haven, Florida image 1

Cute & Cozy in Winter Haven, Florida image 2

Cute & Cozy in Winter Haven, Florida image 3

Cute & Cozy in Winter Haven, Florida image 4

Cute & Cozy in Winter Haven, Florida image 5

Cute & Cozy Guesthouse in Winter Haven

1 bedroom·1 bath

Winter Haven • Florida

4.79(42 reviews)

295,68 $ USD gesamt für 3 Nächte

29. Sept. – 2. Okt. 2026

Front of the house

Front of the house

Newly remodeled Vacation Home with Saltwater Pool

3 bedrooms·2 baths

Winter Haven • Florida

1.075,20 $ USD gesamt für 4 Nächte

26.–30. Sept. 2026