
Winter Springs Rentals

- From $250 per night (USD)
VRBO
Gator Nest: Charming 3-bedroom, 2-bath home, sleeps 6. Excellent for a relaxing, nature getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌅 Lakeside Serenity at Gator Nest 🌅 Experience breathtaking sunsets over Lake Jessup from our large back patio! Nestl ...
From $250 per night (USD)VRBO
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Expedia
Beautiful two bedroom two bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
RiZE at Winter Springs is a beautiful community located in Winter Springs, Florida. Our convenient location provides eas ...
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- From $504 per night (USD)
VRBO
Gator Mansion: Spacious 6-bedroom, 5-bath home, sleeps 12. Perfect for family gatherings.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Gator Mansion offers luxury with 6 bedrooms and 5 baths, perfect for large groups. Enjoy a spacious living area with a 5 ...
From $504 per night (USD)VRBO
- From $266 per night (USD)
Expedia
Gator Den: Comfortable 3-bedroom, 2-bath home, sleeps 6. Ideal for mid-sized groups.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gator Den offers a serene lakefront retreat minutes from the city. This fully furnished home features free WiFi, a smart ...
From $266 per night (USD)Expedia
- From $138 per night (USD)
VRBO
Gator Lodge: Inviting 2-bedroom, 1-bath home, sleeps 4. Perfect for couples or small families.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the charm of Gator Lodge, a cozy retreat near the Black Hammock Wilderness Area. This welcoming space is perf ...
From $138 per night (USD)VRBO
- From $193 per night (USD)
Expedia
Gator Cove: Quaint 2-bedroom, 1-bath cottage, sleeps 4. Great for a peaceful retreat.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a relaxing stay at Gator Cove, a cozy 2-bedroom, 1-bath home with a fully stocked kitchen, washer/dryer, and smart ...
From $193 per night (USD)Expedia
- From $526 per night (USD)
VRBO
Gator Palace: Stylish 5-bedroom, 4-bath home, with upstairs loft. Sleeps 12.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Gator Palace in Oviedo, Florida—a spacious, two-story villa perfect for large families, comfortably sleeping ...
From $526 per night (USD)VRBO
- From $236 per night (USD)
Expedia
Relaxing Oasis: Massage Chair, Game Garage, Large Fenced Backyard, and more
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Discover the perfect blend of comfort and entertainment in our large, cozy, and newly renovated home. Just a short dista ...
From $236 per night (USD)Expedia
- From $197 per night (USD)
VRBO
Paradise in a country setting. 2 BDRM 1100 SQ FT apartment. 1 King ,1 Queen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful,clean spacious and private on an acre and a half, yet close to everything! Imagine yourself and family right h ...
From $197 per night (USD)VRBO
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Expedia
New two story townhome with plenty of outdoor space.
- Bedrooms:
- 6
- Bathrooms:
- 2
- Sleeps:
- 4
Property is on the second and third floors of a three story townhouse. Main front entrance leads to open space Kitchen, ...
Click For PricingExpedia
- From $295 per night (USD)
VRBO
Tranquil, Spacious property within an gated Community
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Tranquil, spacious 5 bedroom with flat screen TVs, 3.5 bathroom and 6.5 acre wooded single family home. Property sit i ...
From $295 per night (USD)VRBO
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Expedia
NEAR THEME PARKS UNIVERSAL - DISNEY AND DOWNTOWN ORLANDO
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a beautiful house 3 Bedrooms 2 Bathrooms washer and dryers HUGE Backyard, very close to Wakavia Springs, 30 min ...
Click For PricingExpedia
- From $66 per night (USD)
VRBO
EFFICIENCY\/ROOM with garage, kitchen bar and a separate entrance from the garage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
The room/efficiency with corner kitchenette is on the first floor of the three story townhome building and is with separ ...
From $66 per night (USD)VRBO
- From $138 per night (USD)
Expedia
Luxury 2 room near Disney
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 1
Near Disney, restaurants, Walmart, Publix , 2 bed 2 bath family friendly, brand new house, near the Sanford internationa ...
From $138 per night (USD)Expedia
- From $185 per night (USD)
VRBO
“Harmony”_
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
“Harmony” is a lovely and comfortable 2 bedroom 1 bathroom 1 car garage duplex. It’s nestled in a quiet and friendly Ov ...
From $185 per night (USD)VRBO
- From $298 per night (USD)
Expedia
3B\/2Ba Home with Commmunity Pool. 30min from Universal Studios
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
In this home, you will find a newly renovated kitchen and bathrooms, with modern detailing and new appliances. There is ...
From $298 per night (USD)Expedia
- From $189 per night (USD)
VRBO
Gator Cottage: Cozy 2-bedroom, 1-bath cottage, sleeps 4. Perfect for a small family.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover tranquility at Lake Jesup Hideaway! Our charming 2BR cottage offers a cozy retreat near Black Hammock in rural ...
From $189 per night (USD)VRBO
- From $129 per night (USD)
Expedia
Gator Hole: Old-Florida Cabin Feeling 2-bedroom, 1.5-bath house, sleeps 4.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the breathtaking view of Florida wildlife or a sunset over Lake Jesup from a large open window overlooking the wat ...
From $129 per night (USD)Expedia
- From $98 per night (USD)
VRBO
Tiny remodel mobile home close to Orlando and Sanford Airport.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a memorable visit when you stay in this unique place. This mobile house is completely renovated on a NON HOA commu ...
From $98 per night (USD)VRBO
- From $173 per night (USD)
Expedia
Florida Guest House with Private pool & WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the beautiful city of Lake Mary! Kick back and relax in this quaint, stylish space. Located in Central Florid ...
From $173 per night (USD)Expedia
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VRBO
Modern Guest Studio 15 mins from SFB Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This guest studio has its own private entrance, kitchen, washer and dryer, bathroom, and all important appliances (TV, F ...
Click For PricingVRBO
- From $255 per night (USD)
Expedia
Fire Pit + Private Yard: Family Home in Longwood!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Plan your next trip to Longwood, FL, with this vacation rental as the focal point for all your Orlando-area adventures! ...
From $255 per night (USD)Expedia
- From $169 per night (USD)
VRBO
Enjoy a tailor made experience at this centrally-located place.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a tailor made experience at this centrally-located place. Centrally located between all the beautiful beaches on ...
From $169 per night (USD)VRBO
- From $142 per night (USD)
Expedia
Cottage with queen bed & nearby pickleball courts
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the beautiful city of Lake Mary! Kick back and relax in this calm, stylish space. Located in Central Florida ...
From $142 per night (USD)Expedia
- From $123 per night (USD)
VRBO
Gorgeous and Cozy Two Bedroom Townhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful townhome has everything you need and is greatly located within miles of attractions, theme parks, college ...
From $123 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Sun-filled oasis with furnished patio, shared pool, & fire pit - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Evergreen Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $249 per night (USD)Expedia
- From $273 per night (USD)
VRBO
16 Mi to Dtwn Orlando: Quiet Apt w\/ Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the best of Florida with ease from this 1-bedroom + bonus room, 1-bath vacation rental! This Lake Mary apartm ...
From $273 per night (USD)VRBO
- From $221 per night (USD)
Expedia
Peaceful family retreat-centrally located for attraction options!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Renovated deluxe spa master bath for the ultimate relaxation after a day of activities! Family board games, fire pit in ...
From $221 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Historic Oviedo Charmer - Close to everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This Oviedo House is nestled in a quiet, residential neighborhood that comfortably hosts a family, group of friends, cou ...
From $179 per night (USD)VRBO
- From $213 per night (USD)
VRBO
Cozy Central Florida Townhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This stylish, updated house is a family-owned, 2 bed / 2 bath townhome located in Casselberry, Florida. Conveniently loc ...
From $213 per night (USD)VRBO
- From $338 per night (USD)
VRBO
WHOLE HOUSE Near Universal & Seaworld
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The whole group will be comfortable in this spacious with 4 BR/3 full baths and unique space Huge garden . We are availa ...
From $338 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Scenic Lakefront Stay | 3BR, 2BA in Oviedo!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
🏡 Welcome to Your Spacious Retreat! Enjoy a private stay in Unit 2, part of a cozy quadruplex with its own entrance. � ...
From $223 per night (USD)Expedia
- From $81 per night (USD)
VRBO
Peaceful Lake Haven | 1BR & Parking in Oviedo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
🏡 Welcome to Your Cozy Escape! Enjoy a private stay in Unit 1, part of a quiet quadruplex with its own entrance. 🛏️ 1 ...
From $81 per night (USD)VRBO
- From $78 per night (USD)
Expedia
Charming 1BR Hideaway | Pet-Friendly & Laundry!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
🏡 Welcome to Your Cozy Getaway! Enjoy a private and comfortable stay in Unit 3, part of a quiet quadruplex with its own ...
From $78 per night (USD)Expedia
- From $147 per night (USD)
VRBO
Vibrant Oviedo 3BR | Pet-Friendly & Fast Wifi!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 2
🏡 Welcome to Your Spacious Home Away from Home! Enjoy a comfortable stay in Unit 4, a private space within a quiet quad ...
From $147 per night (USD)VRBO
- From $676 per night (USD)
Expedia
Gator Manor: Elegant 6-bedroom, 6-bath home, sleeps 12. Ideal for large groups
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Gator Manor, your perfect getaway nestled near the enchanting Black Hammock! This stunning 6-bedroom, 6-bathr ...
From $676 per night (USD)Expedia
- From $467 per night (USD)
VRBO
Spacious 4-bedroom house in lovely Winter Springs near everything
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Winter Springs, this house is a dream. With 4 bedrooms including 2 queen beds, 2 twin bed, and 1 king bed, th ...
From $467 per night (USD)VRBO
- From $356 per night (USD)
Expedia
Moxy Luxe - Charming 4-bedroom house with AC and WiFi in delightful Casselberry
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your new home away from home! This stunning single-level property boasts an open floor plan that is perfect f ...
From $356 per night (USD)Expedia
- From $142 per night (USD)
VRBO
3 bedroom 2 bathroom home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Longwood like a local in this 3-bedroom house. Nestled in a tranquil neighborhood, this gorgeous property off ...
From $142 per night (USD)VRBO
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Expedia
Centrally Located Home w\/ Fenced Yard in Oviedo!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Pets Welcome w/ Fee | Fireplace | Work From Home | Garage w/ Workout Weights Gather loved ones and furry friends and re ...
Click For PricingExpedia