Oakland Vacation Rentals
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Distance from
5 mi
45 rentals in Oakland.
5 Minutes Walk to Shopping and Great Restaurants
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Oak View Place..
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Modern Florida Bungalow: 3 Miles to Winter Garden!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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The following properties within 20 miles of Oakland match all your filters:
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB -near Orlando
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Downtown Winter Garden Cottage ~ 12 Mi to Disney!
Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Downtown Winter Garden Home ~ 12 Mi to Disney!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Modern Winter Garden Cottage: 16 Mi to Disney
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Large Studio Apartment Downtown
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Private In-Law Suite with a lake view in a gated community
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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A place with a view
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Our RV is located in winter garden near downtown
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Lakefront Clermont Retreat w/ Fire Pit!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chic Studio in Winter Garden
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Waterfront Luxury Airstream on An Orange Grove
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Mid Century Hipster
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 3BR King/Queen Free Parking Near Disney
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mystic Cabin Retreat Home w/pool near Orlando, close to Disney!
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Learn how to camp RV style in this Lux RV which sleeps up to 8 people.
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable 1-bedroom right on the bike trail
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Guest room Near Lake Bennet ORL
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury garage apartment in Winter Garden that sleeps four.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Studio Private Entrance 30 Minute From Disney and Universal Studio All new
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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4 Bedroom, 3 Bath Home has 2,602 Square Feet
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Studio Apartment Near Downtown and Disney
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Updated Winter Garden Home w/ Yard & Fire Pit!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Winter Garden Bungalow w/ Gas Grill, Walk to Dtwn!
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Winter Garden Home w/ BBQ, Walk to Dwtn!
Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Dreamy Family Pool House
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn
Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern Private Room With Private Entrance
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Studio in Winter Garden
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Eclectic Escape: Disney Proximity
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stay A While
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lake serenity and natural beauty near Orlando
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Quaint 1Br/Ba entire guest house in heart of Hist. Downtown Winter Garden
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Tranquil Oasis - Pool - Gym- Kid/Pet Friendly
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Studio on the Bike Trail
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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StylishAptWtrGrdnOppLake&Prk&Yrd
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3 2 � Oasis 2acres 10mins from Disney
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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1921 Winter Garden home 22 min from Magic Kingdom & 15 min walking to Plant ST
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Amaizing Villa Flores w/hot tub located 30 minutes from Disney land Atractions.
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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House with large deck, walking distance to Historic Downtown Winter Garden
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cute Studio on the Bike trail
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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All-You-Need Studio Apartment
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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FunTropicalTinyHomeGolfCartLake
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Showing results 1-45 of 45
Frequently Asked Questions about Oakland
- Yes, here are some popular vacation rentals in Oakland that have a pool:
- 5 Minutes Walk to Shopping and Great Restaurants
- The Oak View Place..
- Modern Florida Bungalow: 3 Miles to Winter Garden!
- Yes, here are some popular vacation rentals in Oakland that have internet access:
- 5 Minutes Walk to Shopping and Great Restaurants
- The Oak View Place..
- Modern Florida Bungalow: 3 Miles to Winter Garden!
- Some of the most popular kid friendly rentals in Oakland are:
- 5 Minutes Walk to Shopping and Great Restaurants
- The Oak View Place..
- Modern Florida Bungalow: 3 Miles to Winter Garden!
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