orSearch for vacation rentals in Winter Park.
Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Winter Park area to find the perfect spot for your vacay.
425 Balmoral Rd |
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425 Balmoral RdWinter Park, FL$3,950
Vacation Rentals, Unknown
3 bedroom 2 baths located at the entrance of the beautiful Windsong area, surrounded by picturesque homes. Great location close to great schools and downtown winter park. Property features:...... |
1868 Lake Spier Dr |
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1868 Lake Spier DrWinter Park, FL$2,845
Vacation Rentals, Unknown
This beautiful 3-bedroom, 2-bathroom home features hardwood flooring throughout and an abundance of windows that fill the space with natural light. The spacious kitchen is equipped with a modern...... |
1985 Japonica Rd |
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1985 Japonica RdWinter Park, FL$3,300
Vacation Rentals, Unknown
Charming family home available for rent in a quiet area of Winter Park! This property has a spacious design of 4 bedrooms, a private patio perfect for barbecues and an incredible pool to share with...... |
1185 Village Forest Pl |
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1185 Village Forest PlWinter Park, FL$2,220
Vacation Rentals, Unknown
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare professional...... |
1803 Pineview Cir |
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1803 Pineview CirWinter Park, FL$1,975
Vacation Rentals, Unknown
This beautiful 2 bed / 1 bath 1,029 square foot home is totally refurbished and available for immediate occupancy. Newer kitchen cabinets. Newer bathroom. With a single car carport. This property...... |
2141 Ridge Dr |
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2141 Ridge DrWinter Park, FL$2,670
Vacation Rentals, Unknown
Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or...... |
870 Carver St |
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870 Carver StWinter Park, FL$5,150
Vacation Rentals, Unknown
Welcome to 870 Carver Street, a one-of-a-kind rental offering two distinct, private residences on a single fully fenced property in the heart of Winter Park. The main home is a 2 bedroom, 2 bath...... |
1391 Oneco Ave |
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1391 Oneco AveWinter Park, FL$4,800
Vacation Rentals, Unknown
Available June 1, 2026, this fully renovated 4-bedroom/3-bathroom home in Winter Park, FL, offers ~2,500 sq ft of modern luxury in a top-tier school district. Features include high-end finishes,...... |
1711 Chestnut Ave |
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1711 Chestnut AveWinter Park, FL$4,150
Vacation Rentals, Unknown
Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from Interlachen Country Club and Winter Park...... |
438 Lakeview Ave |
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438 Lakeview AveWinter Park, FL$3,400
Vacation Rentals, Unknown
Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a...... |
1625 Tioga Trl |
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1625 Tioga TrlWinter Park, FL$4,275
Vacation Rentals, Unknown
A RARE FIND IN WINTER PARK!! 4 BEDROOMS, 3 BATHROOMS, POOL, AND FENCED BACKYARD. AVAILABLE FOR MOVE-IN EARLY JUNE. GREAT HOME IN WONDERFUL NEIGHBORHOOD, perfect location with sought after Winter...... |
616 Driver Ave |
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616 Driver AveWinter Park, FL$2,695
Vacation Rentals, Unknown
Fantastic 6 Bedrooms & 3 Bathrooms Huge Home Available 05/07 Located At 616 Driver Ave Winter Park, FL 32789. Limited-time offer! Enjoy $150 off the base rent of $2,845 during months 2, 3, and 4...... |
540 W Comstock Ave |
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540 W Comstock AveWinter Park, FL$2,900
Vacation Rentals, Unknown
Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida's most desirable and high-demand areas, this newly renovated residence at 540 W...... |
2507 Windward Way |
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2507 Windward WayWinter Park, FL$1,895
Vacation Rentals, Unknown
This 2 Bedroom, 2 Bath Attached Villa has been completely remodeled in past 2 years inside and out! NEW Cabinets, NEW Appliances, NEW Tile Floors throughout. Living and Family Room with Fireplace,...... |
1791 Winchester Dr |
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1791 Winchester DrWinter Park, FL$6,000
Vacation Rentals, Unknown
Welcome to Timberlake Shores. This 4/2 one story ranch home offers a peaceful living experience. The generous master suite features a spacious bath and walk-in closet. There are wood floors...... |
4800 Tangerine Ave |
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4800 Tangerine AveWinter Park, FL$1,900
Vacation Rentals, Unknown
Beautiful & Spacious 2-Bedroom, 2-Bath Condo for Rent in Winter Park $1,900/Month Discover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained condo located in...... |
1387 Clay St |
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1387 Clay StWinter Park, FL$2,950
Vacation Rentals, Unknown
Live just minutes from Park Avenue in this beautifully maintained Craftsman home, offering timeless character and modern-day convenience in a prime Winter Park location. Charming Craftsman Home | 3...... |
1430 Lone Feather Trl |
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1430 Lone Feather TrlWinter Park, FL$3,895
Vacation Rentals, Unknown
Welcome to this newly built and well-maintained home in the fabulous Winter Park gated community of Hawk's Crest. A gorgeous open floor plan single-family home with 4 bedrooms, 3.5 bathrooms and...... |
1872 Erudite Way |
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1872 Erudite WayWinter Park, FL$2,500
Vacation Rentals, Unknown
Experience luxury smart home living in the highly desirable, gated community of Grayson Square. This spacious two-story townhome, featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a...... |
1461 Lone Feather Trl |
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1461 Lone Feather TrlWinter Park, FL$3,600
Vacation Rentals, Unknown
Beautiful newer two-story home in Winter Park's exclusive Gated community of Hawk's Crest. Community has lake access with canon launch. The home has a great floor plan that features open dining and...... |
1968 Lanier Ct |
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1968 Lanier CtWinter Park, FL$1,650
Vacation Rentals, Unknown
**TEXT OR SEND ZILLOW MESSAGE FOR ANY SHOWING REQUESTS OR QUESTIONS** ADDRESS: 1968 LANIER CT WINTER PARK This totally remodeled 2 bedroom 1 bath apartment is part of a single floor triplex located...... |
650 Minnesota Ave |
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650 Minnesota AveWinter Park, FL$3,950
Vacation Rentals, Unknown
Beautifully restored 1940's home in A rated school district with 10' ceilings and oversized bedrooms. Hardwood floors, updated, amenities, large back yard patio area with deck, plenty of parking,...... |
1961 Winter Park Rd |
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1961 Winter Park RdWinter Park, FL$3,250
Vacation Rentals, Unknown
Beautifully redone home in A rated school district with large fenced back yard minutes from Park Ave. Updated amenities with porcelain tile floors. For a list of ALL additional properties...... |
3246 Heatherbrook Ct |
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3246 Heatherbrook CtWinter Park, FL$2,800
Vacation Rentals, Unknown
This home at 3246 Heatherbrook Ct in Winter Park is in a quiet, safe, and desirable neighborhood just minutes from shopping, dining, parks, and everyday conveniences. The bedrooms feature fairly...... |
717 Denton Rd |
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717 Denton RdWinter Park, FL$2,099
Vacation Rentals, Unknown
AVAILABLE: May 19, 2026 Pets: OK (Dangerous Pets are not permitted, Pit Bulls, etc.) EASY TO VIEW AT A CONVENIENT TIME SAVE MONEY ON THE APPLICATION FEES: We recommend that you not fill out an...... |
1790 Viburnum Ln |
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1790 Viburnum LnWinter Park, FL$2,610
Vacation Rentals, Unknown
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare professional...... |
1313 Buckingham Rd |
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1313 Buckingham RdWinter Park, FL$3,800
Vacation Rentals, Unknown
**Move-in ready starting June 1st!! | Schedule your tour today! ** Welcome to your new home! This charming 4 bed, 2 bath home in beautiful Winter Park is waiting for you to make it yours. The...... |
3152 Dwarf Pine Ave |
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3152 Dwarf Pine AveWinter Park, FL$1,299
Vacation Rentals, Unknown
Lush mature landscaping is your first impression of this lovely 3 bedroom 2 full bathroom home in the desirable Bel Aire Pines subdivision of Winter Park. The impressive wood burning fireplace is...... |
7433 Betty St |
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7433 Betty StWinter Park, FL$2,245
Vacation Rentals, Unknown
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare professional...... |
1924 Azalea Ave |
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1924 Azalea AveWinter Park, FL$1,995
Vacation Rentals, Unknown
Adorable mid century modern bungalow in Winter Park! This 3 bedroom, 1 bathroom home has been beautifully updated with new tile wood floors in the main living area. The kitchen features white...... |