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Search results; Over 1,000 places in Winter Park

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Explore more homes

Top guest favorite

Room in Winter Park

Stay with Maria

Top Floor French Style Studio.

Jun 2 – 7

R7,533 ZAR for 5 nights

for 5 nights

4.99 out of 5 average rating, 98 reviews

Guest favorite

Room in Winter Park

Stay with MyrianHosting for 8 years,

Winter Park, cozy small room.

Jun 2 – 7

R4,387 ZAR for 5 nights

for 5 nights

4.87 out of 5 average rating, 276 reviews

Top guest favorite

Home in Winter Park

Stylish newly updated home in Winter Park

Free cancellation

Jun 16 – 21

R18,300 ZAR for 5 nights

for 5 nights

4.99 out of 5 average rating, 125 reviews

Superhost

Guesthouse in Winter Park

Cozy guest house close to Downtown Orlando

2 beds

Jun 1 – 6

R9,959 ZAR for 5 nights

for 5 nights

4.85 out of 5 average rating, 157 reviews

Superhost

Tiny home in Winter Park

Comfy Tiny Home @WP. Large Private Deck+Queen bed

2 beds

Jun 1 – 6

R11,702 ZAR for 5 nights

for 5 nights

4.84 out of 5 average rating, 90 reviews

Superhost

Home in Winter Park

Funky Remodeled Otown Bungalow Sleeps 8

7 beds

Jun 23 – 28

R13,545 ZAR for 5 nights

for 5 nights

4.85 out of 5 average rating, 92 reviews

Guest favorite

Apartment in Winter Park

Retro Palm Beach-Style Boudoir

Free cancellation

Aug 1 – 6

R14,304 ZAR for 5 nights

for 5 nights

4.95 out of 5 average rating, 292 reviews

Top guest favorite

Home in Winter Park

The Winter Park Experience

4 beds

Jun 1 – 6

R23,839 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 37 reviews

Top guest favorite

Room in Winter Park

Stay with JenniferReal estate,

Gorgeous Working Person's Hideaway in Winter Park

Jun 1 – 6

R5,743 ZAR for 5 nights

for 5 nights

4.91 out of 5 average rating, 56 reviews

Guest favorite

Apartment in Winter Park

Apt F -Modern Elegance in the Heart of Winter Park

2 queen beds

Jun 4 – 9

R11,654 ZAR for 5 nights

for 5 nights

4.91 out of 5 average rating, 138 reviews

Guest favorite

Loft in Orlando

Contemporary Loft Near Downtown

Free cancellation

Jun 4 – 9

R15,151 ZAR for 5 nights

for 5 nights

4.92 out of 5 average rating, 576 reviews

Top guest favorite

Guesthouse in Orlando

The Loft in College Park

Free cancellation

Jul 4 – 9

R9,112 ZAR for 5 nights

for 5 nights

4.98 out of 5 average rating, 215 reviews

Guest favorite

Guest suite in Orlando

Private guest unit W/Tropical Views! (Not shared)

Free cancellation

Jun 16 – 21

R7,311 ZAR for 5 nights

for 5 nights

4.93 out of 5 average rating, 165 reviews

Top guest favorite

Bungalow in Maitland

Maitland-Orlando Area, FL. Pool House Bungalow

Free cancellation

Jul 8 – 13

R11,634 ZAR for 5 nights

for 5 nights

4.88 out of 5 average rating, 556 reviews

Superhost

Home in Orlando

the guest house orlando

Free cancellation

Jul 16 – 23

R18,256 ZAR for 7 nights

for 7 nights

New place to stay

Home in Winter Park

The Briarcliff

Free cancellation

Jul 6 – 11

R22,991 ZAR for 5 nights

for 5 nights

New place to stay

Superhost

Apartment in Winter Park

Charming Flat in Winter Park

Free cancellation

Jun 1 – 6

R13,032 ZAR for 5 nights

for 5 nights

New place to stay

Superhost

Guesthouse in Orlando

Comfy Studio Guest Suite

Free cancellation

Jun 8 – 13

R8,646 ZAR for 5 nights

for 5 nights

4.91 out of 5 average rating, 119 reviews

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