Oakland, FL, USA Vacation Rentals

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United States Florida Winter Garden vacation rental compare prices direct by owner 1105018

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

4.8 (180)

2 Bedrooms • 4 Guests

$286 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 28090550

Fire Pit & Yard: Updated Winter Garden Home!

4.8 (54)

2 Bedrooms • 4 Guests

$440 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 26549943

Dtwn Winter Garden Home: 12 Mi to Disney!

4.6 (43)

3 Bedrooms • 6 Guests

$279 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 1976653

Walk to Dtwn: Winter Garden Home w/ Patio

4.9 (138)

2 Bedrooms • 4 Guests

$244 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 1976892

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

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United States Florida Clermont vacation rental compare prices direct by owner 24913764

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

4.9 (40)

1 Bedroom • 6 Guests

$277 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 19761678

16 Mi to Disney: Cottage w/ Deck in Winter Garden

4.8 (79)

1 Bedroom • 4 Guests

$181 avg/night

United States Florida Montverde vacation rental compare prices direct by owner 45311275

Pool, Patio + Game Room! Secluded Montverde Home

0.0 (0)

4 Bedrooms • 8 Guests

$507 avg/night

United States Florida Oakland vacation rental compare prices direct by owner 2064515

Historic Oakland Manor House

4.9 (55)

5 Bedrooms • 14 Guests

Available on

United States Florida Oakland vacation rental compare prices direct by owner 2520309

Private Grace Suite in a Magical Inn Near Orlando

5.0 (1)

1 Bedroom • 4 Guests

Available on

United States Florida Oakland vacation rental compare prices direct by owner 9838873

Historic OMHouse- Peacock Room

5.0 (1)

1 Bedroom • 2 Guests

Available on

United States Florida Oakland vacation rental compare prices direct by owner 10071935

Historic Oakland Manor- Mermaid Room

0.0 (0)

1 Bedroom • 2 Guests

Available on

United States Florida Winter Garden vacation rental compare prices direct by owner 27327473

Spacious Garage Apartment in Winter Garden

5.0 (115)

2 Bedrooms • 4 Guests

Available on

United States Florida Winter Garden vacation rental compare prices direct by owner 23665554

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

5.0 (184)

4 Bedrooms • 8 Guests

$563 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 23623702

Winter Garden Experience! Walkable Downtown I Pets

4.9 (101)

2 Bedrooms • 4 Guests

$243 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 40584063

Updated 4/2 Winter Garden Home 20 Min From Disney!

5.0 (9)

4 Bedrooms • 8 Guests

$299 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 33748729

Eclectic Escape:Disney Proximity

4.9 (18)

5 Bedrooms • 10 Guests

Available on

United States Florida Winter Garden vacation rental compare prices direct by owner 11407574

Downtown Winter Garden Mid Century Hipster I Pets

4.8 (107)

3 Bedrooms • 6 Guests

$232 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 24230257

Adorable 1-bedroom right on the bike trail

4.7 (50)

1 Bedroom • 4 Guests

$139 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 36307668

FunTropicalCozyRetreatGolfCartLake

4.7 (117)

2 Bedrooms • 5 Guests

$195 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 37745774

StylishAptWtrGrdnOppLake&Prk&Yrd

4.7 (36)

2 Bedrooms • 6 Guests

$202 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 38387389

Renovated 2BR Near Disney & Winter Garden

4.6 (10)

2 Bedrooms • 5 Guests

Quiet cozy room close to Disney

4.4 (74)

1 Bedroom • 2 Guests

$57 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 36009499

2BR in a house cozy quiet Near Disney Sleeps up 4

4.1 (42)

2 Bedrooms • 4 Guests

$93 avg/night

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