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Our top choices for Winter Springs holiday homes
1. The Longwood Escape • Modern Private Guesthouse Near Orlando
The Longwood Escape • Modern Private Guesthouse Near OrlandoLongwood
The price is AU$232
includes taxes & fees
16 Nov - 17 Nov
2. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!Casselberry
9.8 out of 10, Exceptional, (58 reviews)
"Everything about the house was great. Great house for the price!"
Charles T.
The price is AU$344
includes taxes & fees
17 Nov - 18 Nov
3. Florida Vacation with pool fun for families
Florida Vacation with pool fun for familiesCasselberry
9.0 out of 10, Wonderful, (50 reviews)
"Good location for shops and food etc. quiet neighborhood and host was very nice."
Anonymous traveller
The price is AU$476
includes taxes & fees
16 Nov - 17 Nov
4. Welcoming 2-bedroom house with AC in charming Sanford
Welcoming 2-bedroom house with AC in charming SanfordSanford
10.0 out of 10, Exceptional, (6 reviews)
"Charming and beautifully decorated. The home was so comfortable and was well stocked with everything we could have needed. The backyard was awesome with so many fun things. Would stay again."
Aimee B.
The price is AU$458
includes taxes & fees
1 Dec - 2 Dec
5. Peaceful Private Gated Patio Walk to Mall Publix
Peaceful Private Gated Patio Walk to Mall PublixAltamonte Springs
8.6 out of 10, Excellent, (4 reviews)
"Everything was perfect, clean, and all staff were very polite , friendly and respectful. All were willing to help out, and responded quickly to any and all questions. Thank you again for the nice accommodation. "
Barbara R.
The price is AU$262
includes taxes & fees
23 Nov - 24 Nov
6. Renovated Peaceful Luxury Walk to Mall Park Publix
Renovated Peaceful Luxury Walk to Mall Park PublixAltamonte Springs
9.0 out of 10, Wonderful, (23 reviews)
"Host responded quickly to our texts.Location was excellent for our needs."
Angie Y.
The price is AU$270
includes taxes & fees
16 Nov - 17 Nov
7. Home Sweet Home
Home Sweet HomeSanford
9.4 out of 10, Exceptional, (33 reviews)
"Second time to stay at property and it was ideal. Clean, comfortable and easy"
Aimee B.
The price is AU$450
includes taxes & fees
17 Nov - 18 Nov
8. A Home Where Eclectic Luxury Meets Affordability
A Home Where Eclectic Luxury Meets AffordabilityAltamonte Springs
9.8 out of 10, Exceptional, (131 reviews)
"The property was very well located and convenient to many restaurants. Lovely back yard."
Sandra F.
The price is AU$433
includes taxes & fees
16 Nov - 17 Nov
9. River City Retreat
River City RetreatSanford
9.6 out of 10, Exceptional, (22 reviews)
"Great place to stay at. Host was very good at communicating. The house was bigger than expected. Would definitely recommend staying here again!"
Haleigh C.
The price is AU$332
includes taxes & fees
12 Dec - 13 Dec
10. Spacious 4+1 bedroom house in Sanford with fast WiFi, A/C, & sleeping up to 12!
Spacious 4+1 bedroom house in Sanford with fast WiFi, A/C, & sleeping up to 12!Sanford
10.0 out of 10, Exceptional, (16 reviews)
"Location as described, comfortable and spacious. Great communication and easy check-in/out. Would stay again! "
Justin K.
The price is AU$745
includes taxes & fees
1 Dec - 2 Dec
11. Sunshine Escape Guesthouse ☀
Sunshine Escape Guesthouse ☀Orlando
8.6 out of 10, Excellent, (21 reviews)
"The location worked perfect for our needs in a quiet and safe area. The host was very pleasant and we had a wonderful experience dealing with him and any concerns were met and promptly taken care of. We would definitely stay there again "
Robin R.
The price is AU$241
includes taxes & fees
17 Nov - 18 Nov
12. Spacious 5-bedroom house in gorgeous Winter Park
Spacious 5-bedroom house in gorgeous Winter ParkWinter Park
10.0 out of 10, Exceptional, (5 reviews)
"Rented this property for a friend's engagement party and it worked super well. Host was super nice and great with communication"
Hannah F.
The price is AU$439
includes taxes & fees
16 Nov - 17 Nov
13. Top 1% Modern Japandi Retreat - Jacuzzi No Fee
Top 1% Modern Japandi Retreat - Jacuzzi No FeeWinter Park
10.0 out of 10, Exceptional, (8 reviews)
"Clean house, good location to where we wanted to be!"
Jennifer M.
The price is AU$991
includes taxes & fees
22 Nov - 23 Nov
14. Modern Oasis in Orlando | Private Yard | Cabana
Modern Oasis in Orlando | Private Yard | CabanaFairview Shores
8.6 out of 10, Excellent, (8 reviews)
"It was nice place to stay!"
Jason A.
The price is AU$314
includes taxes & fees
17 Nov - 18 Nov
15. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!College Park
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location, easy access to many amenities.Host genuinely cares about the clienteles well being and that needs are accommodated for if required."
Kevin G.
The price is AU$247
includes taxes & fees
16 Nov - 17 Nov
16. Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful ApopkaApopka
9.4 out of 10, Exceptional, (10 reviews)
"It is very close to the restaurant, shops and parks"
Naiviv
The price is AU$186
includes taxes & fees
16 Nov - 17 Nov
17. Sleeps 10 • Fenced Yard, Pets Welcome, Near Daytona and Orlando
Sleeps 10 • Fenced Yard, Pets Welcome, Near Daytona and OrlandoSanford
9.6 out of 10, Exceptional, (22 reviews)
"Thank you so much we had a wonderful visit and so great to be able to bring our dog he really loved the back yard!"
Miriam R.
The price is AU$659
includes taxes & fees
16 Nov - 17 Nov
18. Modern Tropical Pool Home ⭐️
Modern Tropical Pool Home ⭐️Orlando
9.8 out of 10, Exceptional, (23 reviews)
"We had a great stay and communication with Andy was great!! "
Anonymous traveller
The price is AU$592
includes taxes & fees
16 Nov - 17 Nov
19. Comfy studio in Central Orlando
Comfy studio in Central OrlandoAzalea Park
9.0 out of 10, Wonderful, (2 reviews)
"Hosts were very responsive. Everything is as pictured."
Diondra
The price is AU$222
includes taxes & fees
17 Nov - 18 Nov
20. 1x1 Guest Suite 10 minutes from UCF
1x1 Guest Suite 10 minutes from UCFUnion Park
9.4 out of 10, Exceptional, (8 reviews)
"The room was clean, quiet and very convenient. It is more spacious than what it looks in photos, a nice alternative to a hotel room. Parking was easy and the area feels safe. "
Michael
The price is AU$182
includes taxes & fees
30 Nov - 1 Dec
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Learn more about Winter Springs
Nestled among sparkling lakes, this charming city offers tranquil nature trails and scenic parks perfect for picnicking. Don't miss the farmers' market or the nearby 'Oviedo on the Park' for local flavours and family-friendly events.
