Winter Springs Rentals

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549 Houses

17

Perfect home for a family getaway!!

Florida / Winter Springs

Winter Springs house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$114

Price per night from

$114

Great rentals within 20 miles that match your search

Distance approx 5.21 km from Winter Springs Show on Map

24

NEW! Sleek 4BR Lake Mary House w/Private Backyard

Florida / Lake Mary

Lake Mary house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$207

Responds fast!
avg. 7 minutes

Price per night from

$207

Distance approx 6.92 km from Winter Springs Show on Map

24

Gorgeous Sanford House w/ Yard - Walk to Downtown!

Central Florida / Sanford

Sanford apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$172

Responds fast!
avg. 9 minutes

Price per night from

$172

Distance approx 8.42 km from Winter Springs Show on Map

27

Cozy Longwood Home w/Screened-In Porch & Gas Grill

Florida / Longwood

Longwood house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$161

Responds fast!
avg. 7 minutes

Price per night from

$161

Distance approx 5.66 km from Winter Springs Show on Map

18

Warm and Inviting. Ideally located, 3BR/2BA Home

Florida / Maitland

Maitland house

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Child Friendly

Price per night from

$230

Price per night from

$230

Distance approx 10.03 km from Winter Springs

(4) Excellent 

30

Floating Cottage . . .afloat on the St. Johns River in Florida

Central Florida / Sanford

Sanford cottage

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 24 mi
  • Swimming pool
  • Child Friendly

Price per night from

$160

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$160

Distance approx 4.33 km from Winter Springs Show on Map

(1) Very Good 

25

3 bed/2 both Lake Front home

Florida / Lake Mary

Lake Mary house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 59 mi
  • Child Friendly
  • Air conditioning

Price per night from

$114

Responds fast!
avg. 1 hour 18 minutes

Price per night from

$114

Distance approx 9.3 km from Winter Springs

(1) Excellent 

24

Orlando Area “4+Star” 3BR/2BA Pool Home w/ Patio!

Central Florida / Altamonte Springs

Altamonte Springs house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 7 minutes

Price per night from

$144

Distance approx 13.5 km from Winter Springs

(27) Excellent 

38

Elegant Modern Condo/Apt. in Sunny Orlando !

Central Florida / Orlando

Orlando apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 89 mi
  • Swimming pool
  • Child Friendly
“Fantastic Vacation in Orlando” Thanks to Jan we probably had the best vacation in years. The condo is very well situated. It’s only a five minute drive from restaurants and supermarkets, such as Aldi and WalMart. For us it was very important since we
…see more

Price per night from

$87

Responds fast!
avg. 3 hours 13 minutes

Price per night from

$87

Distance approx 13.09 km from Winter Springs

21

Solana Resort-6bedroom-5 masters-Pool-Spa-Free wifi--Close to Disney

Central Florida / Orlando

Orlando villa

6 13 min stay varies

  • 6 bedrooms
  • sleeps 13
  • min stay varies
  • Child Friendly

Price per night from

$207

Responds fast!
avg. 38 minutes

Price per night from

$207

Distance approx 19.14 km from Winter Springs

22

3150ft2 - Room 4 Rent House Share golf course pool

Central Florida / Orlando

Orlando house

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$230

Price per night from

$230

Distance approx 3.61 km from Winter Springs Show on Map

66

Five-Bedroom House at Gator Palace

Central Florida / Oviedo

Oviedo house

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Nearest beach 65 mi
  • Child Friendly
  • Air conditioning

Price per night from

$345

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$345

Distance approx 10.4 km from Winter Springs

(2) Excellent 

27

Winter Park-College Park-Orlando-1

Central Florida / Winter Park

Winter Park house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 100 mi
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$92

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$92

Distance approx 7.05 km from Winter Springs Show on Map

7

Bedroom for Renting. 4 can sleep.

Central Florida / Orlando

Orlando house

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$138

Distance approx 8.02 km from Winter Springs Show on Map

(2) Excellent 

13

2br - 1000ft2 - Winter Park House

Central Florida / Winter Park

Winter Park house

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 88 mi
  • Child Friendly
  • Air conditioning

Price per night from

$165

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$165

Distance approx 3.55 km from Winter Springs Show on Map

(2) Excellent 

25

Three-Bedroom Two Bath Lake Jesup Home at Gator Den

Central Florida / Oviedo

Oviedo house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 65 mi
  • Child Friendly

Price per night from

$196

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$196

Distance approx 8.8 km from Winter Springs

14

Luxe Quite Relaxing Home by UCF Area

Florida / Union Park

Union Park house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 78 mi
  • Child Friendly
  • Air conditioning

Price per night from

$87

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$87

Distance approx 10.81 km from Winter Springs

29

A great loft apartment in College Park, Orlando.

Central Florida / Orlando

Orlando apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Car not necessary

Price per night from

$129

Price per night from

$129

Distance approx 11.8 km from Winter Springs

34

Altamonte Springs/Bear Lake/ 34min to DISNEY WiFi

Florida / Apopka

Apopka house

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$131

Responds fast!
avg. 3 hours 49 minutes

Price per night from

$131

Distance approx 15.52 km from Winter Springs

(2) Excellent 

32

Deltona Private Oasis Awaits! ONLY 30MIN T0 DAYTONA, 45MIN TO DISNEY & UNIVERSAL

Florida / Deltona

Deltona house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$190

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$190

Distance approx 10.81 km from Winter Springs

44

A great little apartment in College Park, Orlando.

Central Florida / Orlando

Orlando apartment

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Nearest beach 72 mi
  • Child Friendly
  • Air conditioning

Price per night from

$129

Price per night from

$129

Distance approx 10.48 km from Winter Springs

24

NEW! Orlando Condo Only 21 Miles to Disney World!

Florida / Lockhart

Lockhart apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$98

Responds fast!
avg. 39 minutes

Price per night from

$98

Distance approx 6.98 km from Winter Springs Show on Map

24

Longwood Studio w/Pool by Seminole Wekiva Trail

Florida / Longwood

Longwood studio

Studio 3 3 nights min

  • Studio
  • sleeps 3
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$81

Responds fast!
avg. 7 minutes

Price per night from

$81

Distance approx 10.87 km from Winter Springs

24

NEW! Updated Osteen Home w/Dock on St. Johns River

Florida / Osteen

Osteen house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$201

Responds fast!
avg. 39 minutes

Price per night from

$201

Distance approx 6.92 km from Winter Springs Show on Map

24

Victorian Sanford House w/ Patio - Walk Downtown!

Central Florida / Sanford

Sanford house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$288

Responds fast!
avg. 36 minutes

Price per night from

$288

Distance approx 7.06 km from Winter Springs Show on Map

9

.Bedroom for 2 - 3

Central Florida / Orlando

Orlando house

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$138

Distance approx 14.12 km from Winter Springs

(1)  

12

Free delivery and pick to Disney ft wilderness campground,2018 model sleeps 8

Central Florida / Orlando

Orlando camper van

1 7 1 night min

  • 1 bedroom
  • sleeps 7
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$127

Responds fast!
avg. 44 minutes

Price per night from

$127

Distance approx 14.13 km from Winter Springs

10

Wyndham Bonnet Creek Resort: Located adjacent to Walt Disney World Resort

Central Florida / Orlando

Orlando condo

2 8 6 nights min

  • 2 bedrooms
  • sleeps 8
  • 6 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$229

Price per night from

$229

Distance approx 15.45 km from Winter Springs

35

Cozy Home Close to the Airport & Theme Parks

Florida / Ventura

Ventura house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$213

Price per night from

$213

Distance approx 7.46 km from Winter Springs Show on Map

9

Uvera Town House

Central Florida / Altamonte Springs

Altamonte Springs house

3 6 10 nights min

  • 3 bedrooms
  • sleeps 6
  • 10 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$173

Price per night from

$173

Distance approx 7.29 km from Winter Springs Show on Map

22

NEW! Artsy Longwood Condo near Cranes Roost Park!

Florida / Longwood

Longwood condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$110

Responds fast!
avg. 36 minutes

Price per night from

$110

Distance approx 12.21 km from Winter Springs

7

Ferncreek House

Central Florida / Orlando

Orlando house

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$115

Price per night from

$115

Distance approx 6.9 km from Winter Springs Show on Map

27

NEW! Lavish Sanford Apt. w/Gourmet Kitchen & Patio

Central Florida / Sanford

Sanford apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 7 minutes

Price per night from

$138

Distance approx 14.12 km from Winter Springs

(37) Excellent 

45

Disney Area Tropical Water Park Resort & Spa, located in the Four Corners-Disney

Central Florida / Orlando

Orlando townhouse

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Awsome !!” We stayed in Laura's Villas, this was a great place to stay, it was clean, close to club house, pool, can't wait to go back had a blast!!
…see more

Price per night from

$100

Responds fast!
avg. 3 hours 4 minutes

Price per night from

$100

Distance approx 14.12 km from Winter Springs

28

WESTRIDGE Pet Friendly 3 bedroom 2 Bath Pool Home.Solar heating; free wifi

Central Florida / Orlando

Orlando house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$148

Price per night from

$148

Distance approx 9.39 km from Winter Springs

34

Casa Vista Verde II Orlando Area 1/1 Pool Disney Daytona Universal Dream House &

Central Florida / Altamonte Springs

Altamonte Springs apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$104

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$104

Distance approx 16.08 km from Winter Springs

(1) Excellent 

26

Luxury 4 bed villa in prime location; 50051

Central Florida / Orlando

Orlando house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$160

Price per night from

$160

Distance approx 9.16 km from Winter Springs

50

Orlando Area 5BR/2BA Home w/ Jacuzzi!

Florida / Wekiva Springs

Wekiva Springs house

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$195

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$195