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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 9 – 14

R7,234 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 16 – 21

R4,391 ZAR for 5 nights

for 5 nights

4.87 out of 5 average rating, 277 reviews

Top guest favorite

Home in Winter Park

Stylish newly updated home in Winter Park

Free cancellation

Jul 12 – 17

R20,093 ZAR for 5 nights

for 5 nights

4.99 out of 5 average rating, 127 reviews

Home in Winter Park

10 min to Winter Park, Games, Gym, King bd, Coffee

Free cancellation

Jun 29 – Jul 4

R13,788 ZAR for 5 nights

for 5 nights

New place to stay

Superhost

Tiny home in Winter Park

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

2 beds

Jun 3 – 8

R11,293 ZAR for 5 nights

for 5 nights

4.84 out of 5 average rating, 90 reviews

Guest favorite

Room in Winter Park

Stay with Emily

Stones-Throw of Disney - NO secret cleaning fee!

Jul 6 – 11

R5,197 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 37 reviews

Superhost

Room in Orlando

Stay with JamieTeacher,

Downtown Orlando Room 2

Jun 15 – 20

R4,348 ZAR for 5 nights

for 5 nights

4.71 out of 5 average rating, 548 reviews

Home in Winter Park

3BR Townhome + Private Bath + Near Rollins College

3 beds

Jun 20 – 25

R22,547 ZAR for 5 nights

for 5 nights

New place to stay

Top guest favorite

Home in Winter Park

Cozy Winter Park Bungalow

Free cancellation

Jun 27 – Jul 2

R13,829 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 7 reviews

Top guest favorite

Home in Orlando

Cozy Orlando Home @ Baldwin Park

Free cancellation

Jul 20 – 25

R16,863 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 16 reviews

Guest favorite

Home in Orlando

City Charmer

Free cancellation

Jun 15 – 20

R12,727 ZAR for 5 nights

for 5 nights

4.92 out of 5 average rating, 79 reviews

Guest favorite

Home in Orlando

Charming Home Close to Golf + Car Rental and more

9 beds

Jun 15 – 20

R13,824 ZAR for 5 nights

for 5 nights

4.89 out of 5 average rating, 28 reviews

Superhost

Apartment in Winter Park

Cozy by the Creek

Free cancellation

Jun 9 – 14

R14,721 ZAR for 5 nights

for 5 nights

New place to stay

Top guest favorite

Guest suite in Eatonville

Private entrance/bathroom 10 min from DT Orlando

Free cancellation

Jul 12 – 17

R7,318 ZAR for 5 nights

for 5 nights

4.99 out of 5 average rating, 158 reviews

Top guest favorite

Home in Winter Park

The Winter Park Experience

4 beds

Jun 3 – 8

R23,862 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 39 reviews

Superhost

Home in Winter Park

Cozy home 5min to Park Ave and Downtown Orlando

3 beds

Jun 21 – 26

R13,122 ZAR for 5 nights

for 5 nights

4.83 out of 5 average rating, 18 reviews

Top guest favorite

Room in Orlando

Stay with RezaHosting for 8 years,

Orlando Oasis

Jun 3 – 8

R6,469 ZAR for 5 nights

for 5 nights

4.96 out of 5 average rating, 116 reviews

Guest favorite

Apartment in Winter Park

Retro Palm Beach-Style Boudoir

Free cancellation

Aug 1 – 6

R14,318 ZAR for 5 nights

for 5 nights

4.95 out of 5 average rating, 292 reviews

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