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Winter Springs
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Over 1,000 places in Winter Springs
Guest favorite
Guest favorite
Condo in Davenport
Airy Resort Condo, Bahama Bay, 10 miles to Disney!
5 beds
5 beds
May 5 – 10
May 5 – 10
$125
$107
night
$107 per night, originally $125
4.98 out of 5 average rating, 48 reviews
4.98 (48)
Guest favorite
Guest favorite
Home in Casselberry
Moxy Luxe Vacation / Heated Pool/ King Bed Ste
5 beds
5 beds
Jun 10 – 15
Jun 10 – 15
$245
night
$245 per night
4.88 out of 5 average rating, 8 reviews
4.88 (8)
Superhost
Superhost
Home in Casselberry
Mirror Manor Lakehouse
9 beds
9 beds
Apr 13 – 18
Apr 13 – 18
$535
$403
night
$403 per night, originally $535
4.94 out of 5 average rating, 16 reviews
4.94 (16)
Guest favorite
Guest favorite
Villa in Kissimmee
Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub
14 beds
14 beds
May 1 – 7
May 1 – 7
$333
$244
night
$244 per night, originally $333
4.98 out of 5 average rating, 98 reviews
4.98 (98)
Guest favorite
Guest favorite
Home in Kissimmee
Storey Lake - Amazing Pool & Peloton - Game Room
9 beds
9 beds
May 13 – 18
May 13 – 18
$299
night
$299 per night
4.92 out of 5 average rating, 103 reviews
4.92 (103)
Guest favorite
Guest favorite
Guest suite in Winter Springs
Modern Guest Studio 15 mins from SFB Airport
1 queen bed
1 queen bed
May 12 – 17
May 12 – 17
$64
night
$64 per night
4.97 out of 5 average rating, 64 reviews
4.97 (64)
Guest favorite
Guest favorite
Home in Oviedo
Peaceful & Private Estate Perfect for Large Groups
12 beds
12 beds
Apr 2 – 7
Apr 2 – 7
$730
$610
night
$610 per night, originally $730
4.93 out of 5 average rating, 43 reviews
4.93 (43)
Home in Kissimmee
Disney Home Retreat| Resort & Private Pool!
8 beds
8 beds
May 2 – 7
May 2 – 7
$185
night
$185 per night
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favorite
Guest favorite
Home in Oviedo
Orlando Heated*Pool Home close to Disney/UCF
5 beds
5 beds
Aug 1 – 6
Aug 1 – 6
$195
night
$195 per night
5.0 out of 5 average rating, 32 reviews
5.0 (32)
Guest favorite
Guest favorite
Home in Oviedo
4 bedroom Modern pool home, close to UCF&Boombah
6 beds
6 beds
Jun 24 – 29
Jun 24 – 29
$200
night
$200 per night
4.92 out of 5 average rating, 281 reviews
4.92 (281)
Guest favorite
Guest favorite
Home in Oviedo
3 bedroom Modern pool home,close to UCF&Boombah
6 beds
6 beds
May 28 – Jun 2
May 28 – Jun 2
$189
night
$189 per night
4.95 out of 5 average rating, 76 reviews
4.95 (76)
Superhost
Superhost
Home in Winter Springs
Pure Vida - Your home away from home!
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$170
night
$170 per night
4.88 out of 5 average rating, 8 reviews
4.88 (8)
Guest favorite
Guest favorite
Home in Sanford
⭐ Beautiful 4/2, 🏌Golf, 🧡 Pool & 🎮 Games!
12 beds
12 beds
Apr 1 – 6
Apr 1 – 6
$267
$152
night
$152 per night, originally $267
4.93 out of 5 average rating, 134 reviews
4.93 (134)
Guest favorite
Guest favorite
Townhouse in Orlando
★Modern DT Home★King Bed☀️Patios✔Long Stays⚡️WiFi★
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
$181
$158
night
$158 per night, originally $181
4.95 out of 5 average rating, 138 reviews
4.95 (138)
Guest favorite
Guest favorite
Home in Altamonte Springs
Orlando Poolside Oasis
Apr 6 – 11
Apr 6 – 11
$281
$202
night
$202 per night, originally $281
4.97 out of 5 average rating, 61 reviews
4.97 (61)
Guest favorite
Guest favorite
Guesthouse in Oviedo
Gated Luxury Country Home on Private 35 Acres
2 beds
2 beds
Apr 8 – 13
Apr 8 – 13
$93
night
$93 per night
4.95 out of 5 average rating, 239 reviews
4.95 (239)
Guest favorite
Guest favorite
Home in Casselberry
Luxurious lakefront home near DT and Winter Park
5 beds
5 beds
Apr 15 – 20
Apr 15 – 20
$311
night
$311 per night
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favorite
Guest favorite
Home in Oviedo
2 Bdrm Cottage near UCF & trails, No cleaning fee
2 queen beds
2 queen beds
Apr 17 – 22
Apr 17 – 22
$143
night
$143 per night
4.95 out of 5 average rating, 116 reviews
4.95 (116)
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