Winter Springs vacation rentals

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Top-rated vacation rentals in Winter Springs

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guest suite in Altamonte Springs
Comfortable Guest Suite-Stylish Altamonte Springs!
Enjoy a stylish guest experience at this centrally-located Altamonte Springs Florida guest suite. This luxury 830 sq ft unit offers a living room, kitchenette, bedroom, bathroom and large pool in the peaceful Spring Valley Farms residential community. It is located 8 miles north of downtown Orlando, a primo location close to downtown, both ocean coasts, Wakiwa Springs State Park, theme parks (Disney, Universal, SeaWorld, more), Crane's Roost, and many other great destinations in central Florida!
Sep 14 – 21
$99 per night
4.96 out of 5 average rating, 137 reviews
Guest favorite
Bungalow in Maitland
Maitland-Orlando Area, FL. Pool House Bungalow
Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.
Aug 22 – 29
$80 per night
4.86 out of 5 average rating, 484 reviews
Guest favorite
Guest suite in Altamonte Springs
St. Augustine suite
Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting
Jun 8 – 15
$78 per night
4.95 out of 5 average rating, 310 reviews

Popular amenities for Winter Springs vacation rentals

Stay near Winter Springs's top sights

Oviedo Mall16 locals recommend
Townhouse Restaurant15 locals recommend
Regal Oviedo Mall10 locals recommend
Spring Hammock Preserve6 locals recommend
Publix Super Market at Winter Springs Town Center3 locals recommend
Target6 locals recommend

Other great vacation rentals in Winter Springs

Guest favorite
Guest suite in Casselberry
“Jungle Hideout” w/ Pool near (Orlando) WinterPark
Apr 4 – 11
$83 per night
4.8 out of 5 average rating, 249 reviews
Guest favorite
Townhouse in Winter Park
Beautiful Downtown Winter Park
Jun 15 – 22
$109 per night
4.98 out of 5 average rating, 193 reviews
Guest favorite
Home in Altamonte Springs
Eclectic Home Where Luxury Meets Affordability
Aug 24 – 31
$173 per night
4.97 out of 5 average rating, 274 reviews
Guest favorite
Guest suite in Geneva
The Weathered Inn at Cedar Knoll Flying Ranch
Apr 28 – May 5
$112 per night
4.95 out of 5 average rating, 216 reviews
Guest favorite
Home in Oviedo
4 bedroom Modern pool home, close to UCF&Boombah
Feb 15 – 22
$193 per night
4.92 out of 5 average rating, 279 reviews
Guest favorite
Home in Winter Park
Guest Suite in Winter Park/Orlando
Apr 28 – May 5
$66 per night
4.9 out of 5 average rating, 120 reviews
Guest favorite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
May 29 – Jun 5
$171 per night
4.95 out of 5 average rating, 332 reviews
Guest favorite
Farm stay in Orlando
Charming Guesthouse at Pine & Oak Place
Jan 28 – Feb 4
$105 per night
4.9 out of 5 average rating, 155 reviews
Guest favorite
Apartment in Winter Park
Get a Little Glam in a Retro Palm Beach-Style Boudoir
Jun 28 – Jul 5
$105 per night
4.95 out of 5 average rating, 280 reviews
Guest favorite
Home in Sanford
Clean, cozy home in a GREAT location
May 27 – Jun 3
$113 per night
4.97 out of 5 average rating, 206 reviews
Superhost
Treehouse in Geneva
Treehouse at Danville
Dec 22 – 27
$230 per night
4.89 out of 5 average rating, 908 reviews
Guest favorite
Bungalow in Altamonte Springs
Villa Mariana - Private & Cozy!
Jun 12 – 19
$71 per night
4.86 out of 5 average rating, 322 reviews

Other great vacation rentals in Winter Springs

Superhost
Home in Winter Springs
Pure Vida - Your home away from home!
Jun 21 – 28
$162 per night
4.86 out of 5 average rating, 7 reviews
Guest favorite
Home in Winter Springs
Modern Lakefront House (Family Friendly)
Jan 23 – 30
$207 per night
4.94 out of 5 average rating, 82 reviews
Guest favorite
Guesthouse in Lake Mary
Cozy Cottage in the heart of Lake Mary
Aug 11 – 18
$78 per night
4.98 out of 5 average rating, 56 reviews
Guest favorite
Home in Casselberry
Spacious 3 BR Home Perfect for Orlando Getaway
Sep 2 – 9
$147 per night
5.0 out of 5 average rating, 37 reviews
Guest favorite
Home in Casselberry
Moxy Luxe Vacation / Heated Pool/ King Bed Ste
Nov 19 – 26
$257 per night
5.0 out of 5 average rating, 7 reviews
Guest favorite
Place to stay in Oviedo
Harmony
Aug 1 – 8
$199 per night
4.97 out of 5 average rating, 33 reviews
Superhost
Home in Winter Park
ꜱʟᴇᴇᴘꜱ 4, ᴡɪɴᴛᴇʀ ᴘᴀʀᴋ & ᴅᴏᴡɴᴛᴏᴡɴ
May 10 – 17
$120 per night
4.9 out of 5 average rating, 39 reviews
Guest favorite
Home in Longwood
Tailor made for you.
Oct 23 – 30
$135 per night
4.92 out of 5 average rating, 12 reviews
Guest favorite
Apartment in Winter Park
The Lake House
Aug 21 – 28
$76 per night
4.88 out of 5 average rating, 25 reviews
Guest favorite
Apartment in Orlando
Parent's Retreat!
Aug 21 – 28
$99 per night
5.0 out of 5 average rating, 59 reviews
Guest favorite
Home in Oviedo
Peaceful & Private Estate Perfect for Large Groups
Jun 15 – 22
$707 per night
4.93 out of 5 average rating, 42 reviews
Superhost
Home in Oviedo
Complete Modern House
Aug 16 – 23
$211 per night
4.83 out of 5 average rating, 12 reviews

Quick stats about vacation rentals in Winter Springs

Total rentals

80 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

2.8K reviews

Nightly prices starting at

$10 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Winter Springs?

    Yes! Work meets play with ease at over 30 vacation rentals in Winter Springs featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winter Springs?

    Four-legged friends are welcome in Winter Springs. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there Winter Springs vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Winter Springs, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Winter Springs?

    Experience the best of Winter Springs with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Winter Springs have wireless internet?

    Absolutely! We offer over 50 house rentals with wireless internet in Winter Springs. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Winter Springs?

    Winter Springs has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Winter Springs have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Winter Springs. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Winter Springs?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wireless internet, over 50 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore