Winter Park, FL Homes for Rent with Pool

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  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Townhouse for Rent

  2539 Antilles Dr, Winter Park, FL 32792

  Welcome to 2539 Antilles Dr, Winter Park, FL – a beautiful corner unit townhouse in the highly desirable Windward Square. As you step inside, you’re welcomed by a cozy living room that seamlessly leads into the kitchen, featuring a new dishwasher and plenty of cabinet space. As you continue walking through the house you will notice the 3 spacious bedrooms and 2 bathrooms. Outside, you'll find a

  Allie George CORCORAN PREMIER REALTY

  2539 Antilles Dr, Winter Park, FL 32792
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  $1,075 - $2,325 per month

  The Taylor at Winter Park

  Studio-3 Beds

  2000 Village Ln, Winter Park, FL 32792

  5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

  2000 Village Ln, Winter Park, FL 32792
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  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 11C, Winter Park, FL 32789

  Lakefront Community on Skiable Lake Killarney with Private Community Ramp, Community Deck. Heated Pool.Well maintained second floor unit with views of the Lake. 2 Bedroom/2 Bath with Balcony overlooking Courtyard.Spacious Rooms, expanded Kitchen, Luxury Vinyl-Tile Floors in Living and Dining Room. Excellent Winter Park Location. Walk to Shopping, Restaurants. Movies and minutes to

  Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 11C, Winter Park, FL 32789
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  $1,538 - $2,943 per month

  Stonecastle Apartment Homes

  1-3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
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  /19

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 2108, Winter Park, FL 32792

  This 2 bedroom, 2 bathroom condo is located in Winter Park's desirable Four Seasons community. Enjoy all Winter Park has, Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  200 Saint Andrews Blvd Unit 2108, Winter Park, FL 32792
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  $1,374 - $1,695 per month

  Solis at Winter Park

  1-2 Beds

  7502 Sun Key Blvd, Winter Park, FL 32792

  Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

  7502 Sun Key Blvd, Winter Park, FL 32792
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  $1,235 per month

  • 1 Bed
  • 1 Bath
  • 756 Sq Ft
  • Condo for Rent

  261 Scottsdale Square Unit 261, Winter Park, FL 32792

  Spacious & Cozy 1 Bed/1 Bath Apartment for Rent – Prime Location Near Important Universities!Don’t miss this opportunity to live in a prime location with all the amenities you need nearby! Schedule a tour today and see why this apartment is the perfect place to call home.Discover your perfect home in this bright and spacious 1-bedroom, 1-bathroom apartment, offering comfort and convenience in a

  Juan Campana AGENT TRUST REALTY CORPORATION

  261 Scottsdale Square Unit 261, Winter Park, FL 32792
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  $1,292 - $1,936 per month

  Venue At Winter Park

  1-3 Beds

  5 Autumn Breeze Way, Winter Park, FL 32792

  Come home to Venue—a community nestled in the heart of Winter Park. Venue is designed to make your living experience better than it has ever been before.When it comes to finding the perfect floor plan for your lifestyle, we have you covered. Choose from our newly renovated 1, 2, and 3-bedroom residences offering refined interior finishes and premier features that are sure to fit all of your

  5 Autumn Breeze Way, Winter Park, FL 32792
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  $1,700 per month

  • 2 Beds
  • 1.5 Baths
  • 1,281 Sq Ft
  • Condo for Rent

  4880 Tangerine Ave Unit 4880, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Clean Winter Park Condo for Rent in Wrenwood! 2-Story Condo with 2 Bedrooms, 1.5 Bathrooms, 1,281 sqft. under air. Features include spacious living area downstairs, Carpeted upstairs bedrooms with walk-in closets, indoor laundry and private screened porch. Community offers quiet setting, Mature Landscaping & Community Pool. Location offers close

  Rick Protheroe RE/MAX TOWN & COUNTRY REALTY

  4880 Tangerine Ave Unit 4880, Winter Park, FL 32792
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  $1,230 - $2,485 per month

  Signal Pointe

  1-3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  2500 Howell Branch Rd, Winter Park, FL 32792
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  $1,550 per month

  • 2 Beds
  • 2 Baths
  • 802 Sq Ft
  • Condo for Rent

  7340 Swallow Run Unit 7340, Winter Park, FL 32792

  Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

  Bobby Mills METRO CITY REALTY

  7340 Swallow Run Unit 7340, Winter Park, FL 32792
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  $1,629 - $1,899 per month

  The Vista at Winter Park

  2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  Get up to %50 off - **Divided evenly over 12 months**Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!Take advantage of exclusive offers available! Valid until 04/30/2025 on specific units only!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the

  4704 Lucier Ct, Winter Park, FL 32792
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  /17

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 784 Sq Ft
  • Condo for Rent

  7268 Swallow Run Unit 7268, Winter Park, FL 32792

  This 2-bedroom, 2-bathroom condominium at 7268 Swallow Run in Winter Park, Florida, offers 784 square feet of comfortable living space. The unit includes a washer and dryer for added convenience. Located near University Boulevard and Goldenrod Road, it provides easy access to shopping centers, restaurants, and major highways. The community features a swimming pool for residents to enjoy. The

  Alejandro Bastidas MY REALTY GROUP, LLC.

  7268 Swallow Run Unit 7268, Winter Park, FL 32792
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  $1,411 - $2,027 per month

  Atlas at Winter Park

  1-3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  $3,400 per month

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • House for Rent

  1850 Whitehall Dr, Winter Park, FL 32789

  This is a wonderful, furnished, pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. This 3 bedroom 2 bath home has an open floor plan with family room/dining room combo, a wonderful family room overlooking the lush tropical landscape of the backyard with a state of the art in ground pool. Enjoy the weekends lounging around the black bottom pool and the lush

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1850 Whitehall Dr, Winter Park, FL 32789
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  $1,592 - $1,908 per month

  POSTE Winter Park

  1-2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  800 Semoran Park Dr, Winter Park, FL 32792
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  $1,649 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Townhouse for Rent

  3271 Forest Oaks Ct Unit 110, Winter Park, FL 32792

  Welcome to this beautifully updated townhouse, ideally located in the sought-after Winter Park community. Featuring 2 spacious bedrooms and 2.5 bathrooms, this home offers the perfect blend of comfort and style for modern living. Enjoy the convenience of a community pool, providing a refreshing retreat on warm Florida days. The included washer and dryer make laundry day a breeze, adding ease to

  Dean D Nikolic PMI PROPERTY ALLIANCE

  3271 Forest Oaks Ct Unit 110, Winter Park, FL 32792
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  $1,250 - $1,800 per month

  Park Apartments

  1-3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  7528 Park Promenade Dr, Winter Park, FL 32792
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  $1,175 per month

  • 1 Bed
  • 1 Bath
  • 549 Sq Ft
  • Condo for Rent

  3035 George Mason Ave Unit C, Winter Park, FL 32792

  MOVE -In READY! Water/Sewer INCLUDED! Second floor perch where price and location put you right where you want to be, with no noisy neighbors above you! Walking distance to grocery and commerce. Washer & Dryer included! Cool, easy-to-clean laminate flooring, and ceiling fans. Community pool, playground. Perfect for first time renter! Plan to see this condo and get your application in today!

  Marcus Phillips REAL PROPERTY MANAGEMENT SUNSTATE

  3035 George Mason Ave Unit C, Winter Park, FL 32792
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  $1,032 - $1,543 per month

  Carlton Arms of Winter Park

  Studio-3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  *Call or email for today’s availabilityCarlton Arms of Winter Park, a well-established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff, offers an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  300 Jamestown Dr, Winter Park, FL 32792
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  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 207, Winter Park, FL 32789

  Welcome to this beautifully renovated 2-bedroom, 1-bathroom second-floor condo on picturesque Lake Killarney. This move-in-ready gem offers the perfect blend of modern conveniences and serene lakefront living. The stylish kitchen features granite countertops, a contemporary backsplash, and brand-new stainless-steel appliances, including a dishwasher and a convenient combination washer/dryer. The

  Monika Kenney PALMANO GROUP RE BROKERAGE LLC

  151 N Orlando Ave Unit 207, Winter Park, FL 32789
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  $1,110 - $2,010 per month

  District On Baldwin Park

  Studio-3 Beds

  5590 Baldwin Park St, Orlando, FL 32807

  Join us at District on Baldwin Park in Orlando, where you'll revel in luxurious apartment living and resort-style amenities minutes from shopping, entertainment, restaurants and recreation. Lounge by one of our three sparkling pools, sip a cup of coffee and surf the net in our Internet cafe?? or chat with neighbors over cards in our clubhouse. At District on Baldwin Park, you get the resort

  5590 Baldwin Park St, Orlando, FL 32807
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  $1,749 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit D215, Winter Park, FL 32789

  This fabulous 3BD/2BTH second-floor condominium end unit. The kitchen features stainless steel appliances, oak cabinets and stunning wood floors greeting you as you enter the unit. Flowing from the living room to the dining room and down the hall. Spacious open floor concept with a sizeable living room boasting large sliding glass doors leading to your private patio while allowing for plenty of

  Fayola Adgar THE LISTING REAL ESTATE MANAGEMENT

  1695 Lee Rd Unit D215, Winter Park, FL 32789
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  $1,350 per month

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft
  • Condo for Rent

  169 Lewfield Cir Unit 169, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Rental Opportunity in Winter Park! Don’t miss this INCREDIBLE OPPORTUNITY! This 1-bedroom, 1-bathroom condo in Stratford at Winter Park offers the perfect blend of comfort, convenience, and lifestyle.Prime Location:Minutes away from shopping, dining, entertainment, and easy access to major highways.Spacious 678 sqft with modern

  Estela Gonzalez LPT REALTY, LLC

  169 Lewfield Cir Unit 169, Winter Park, FL 32792
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  /19

  $2,700 per month

  • 2 Beds
  • 1 Bath
  • 804 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 131, Winter Park, FL 32789

  Enjoy lakefront living in this 2-bedroom, 1-bath end-unit condo in Lake Killarney Condos. Located on private, navigable Lake Killarney, this fully renovated home offers stunning sunset views from the living room, kitchen, dining area, and master bedroom. The unit features high ceilings, bamboo wood flooring, recessed lighting, a modern kitchen with granite countertops, stainless steel appliances,

  Adriana Montes MBA ? FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 131, Winter Park, FL 32789
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  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit C103, Winter Park, FL 32789

  Charming condo for Lease! location , Location , location ! This 2-bedroom, 1-bathroom apartment offers an open layout with plenty of natural light, a spacious living area, and a well-equipped kitchen with brand new interior paint job.Enjoy the convenience of in-unit laundry and modern amenities throughout. The apartment is situated in a serene community, offering easy access to shopping, dining,

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C103, Winter Park, FL 32789
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  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 816, Winter Park, FL 32792

  Charming 2-Bedroom, 2-Bathroom Condo in Winter Park – Move-In Ready!This lovely second-floor unit in Golfside Villas features brand-new carpet installed in 2025! Step into a spacious, open-concept kitchen and living area, offering a comfortable and inviting space to relax and entertain.The master bedroom includes an en-suite bathroom, while the generously sized second bedroom also boasts

  Yuly Rodriguez DOUGLAS EDMUND REAL ESTATE LLC

  1000 S Semoran Blvd Unit 816, Winter Park, FL 32792
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  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
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  $3,500 per month

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Condo for Rent

  4392 Wardell Place Unit 102, Orlando, FL 32814

  Welcome to this charming, first floor, corner-unit condo in the heart of Baldwin Park! This impressive condo features an oversized wrap around patio, an attached one car garage and has been fully updated throughout! Lease stress-free with a New HVAC (2022), New Paint (2022), all New Luxury Vinyl Plank Flooring throughout (2022), Brand new Refrigerator, Microwave, Range & Disposal (2024), New

  Lindsey Hahn ALL REAL ESTATE & INVESTMENTS

  4392 Wardell Place Unit 102, Orlando, FL 32814

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