Over 1,000 places in Winter Springs

Guest favorite
Condo in Davenport
Airy Resort Condo, Bahama Bay, 10 miles to Disney!
5 beds
May 5 – 10
4.98 out of 5 average rating, 48 reviews
Guest favorite
Home in Casselberry
Moxy Luxe Vacation / Heated Pool/ King Bed Ste
5 beds
Jun 10 – 15
4.88 out of 5 average rating, 8 reviews
Superhost
Home in Casselberry
Mirror Manor Lakehouse
9 beds
Apr 13 – 18
4.94 out of 5 average rating, 16 reviews
Guest favorite
Villa in Kissimmee
Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub
14 beds
May 1 – 7
4.98 out of 5 average rating, 98 reviews
Guest favorite
Home in Kissimmee
Storey Lake - Amazing Pool & Peloton - Game Room
9 beds
May 13 – 18
4.92 out of 5 average rating, 103 reviews
Guest favorite
Guest suite in Winter Springs
Modern Guest Studio 15 mins from SFB Airport
1 queen bed
May 12 – 17
4.97 out of 5 average rating, 64 reviews
Guest favorite
Home in Oviedo
Peaceful & Private Estate Perfect for Large Groups
12 beds
Apr 2 – 7
4.93 out of 5 average rating, 43 reviews
Home in Kissimmee
Disney Home Retreat| Resort & Private Pool!
8 beds
May 2 – 7
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Oviedo
Orlando Heated*Pool Home close to Disney/UCF
5 beds
Aug 1 – 6
5.0 out of 5 average rating, 32 reviews
Guest favorite
Home in Oviedo
4 bedroom Modern pool home, close to UCF&Boombah
6 beds
Jun 24 – 29
4.92 out of 5 average rating, 281 reviews
Guest favorite
Home in Oviedo
3 bedroom Modern pool home,close to UCF&Boombah
6 beds
May 28 – Jun 2
4.95 out of 5 average rating, 76 reviews
Superhost
Home in Winter Springs
Pure Vida - Your home away from home!
3 beds
Apr 1 – 6
4.88 out of 5 average rating, 8 reviews
Guest favorite
Home in Sanford
⭐ Beautiful 4/2, 🏌Golf, 🧡 Pool & 🎮 Games!
12 beds
Apr 1 – 6
4.93 out of 5 average rating, 134 reviews
Guest favorite
Townhouse in Orlando
★Modern DT Home★King Bed☀️Patios✔Long Stays⚡️WiFi★
3 beds
Apr 21 – 26
4.95 out of 5 average rating, 138 reviews
Guest favorite
Home in Altamonte Springs
Orlando Poolside Oasis
Apr 6 – 11
4.97 out of 5 average rating, 61 reviews
Guest favorite
Guesthouse in Oviedo
Gated Luxury Country Home on Private 35 Acres
2 beds
Apr 8 – 13
4.95 out of 5 average rating, 239 reviews
Guest favorite
Home in Casselberry
Luxurious lakefront home near DT and Winter Park
5 beds
Apr 15 – 20
5.0 out of 5 average rating, 12 reviews
Guest favorite
Home in Oviedo
2 Bdrm Cottage near UCF & trails, No cleaning fee
2 queen beds
Apr 17 – 22
4.95 out of 5 average rating, 116 reviews