Oakland, FL, USA Vacation rentals • comparison for Airbnb, Vrbo and Booking prices

United States Florida Oakland vacation rental compare prices direct by owner 33578029

Modern Florida Bungalow: 3 Miles to Winter Garden!

4.9 (53)

2 Bedrooms • 5 Guests

$237 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 (132)

2 Bedrooms • 4 Guests

$205 avg/night

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

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

4.9 (164)

1 Bedroom • 4 Guests

$165 avg/night

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

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

4.9 (54)

1 Bedroom • 6 Guests

$219 avg/night

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

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

4.8 (169)

2 Bedrooms • 4 Guests

$261 avg/night

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

Dtwn Winter Garden Home: 12 Mi to Disney!

4.8 (37)

3 Bedrooms • 7 Guests

$244 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 (71)

1 Bedroom • 4 Guests

$146 avg/night

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

Fire Pit & Yard: Updated Winter Garden Home!

4.8 (46)

2 Bedrooms • 4 Guests

$301 avg/night

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 2064515

Historic Oakland Manor House

4.9 (54)

5 Bedrooms • 15 Guests

$731 avg/night

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 23665554

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disny

5.0 (153)

4 Bedrooms • 8 Guests

$646 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 36772022

StylishAptWtrGrdnOppLake & Prk & Yrd

5.0 (90)

2 Bedrooms • 6 Guests

$188 avg/night

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

Winter Garden Experience! Walkable Downtown I Pets

4.9 (88)

2 Bedrooms • 4 Guests

$211 avg/night

United States Florida Winter Garden vacation rental compare prices direct by owner 26602591

Luxury Winter Garden Getaway Near Disney and Parks

4.9 (145)

3 Bedrooms • 8 Guests

$247 avg/night

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

Downtown Winter Garden Mid Century Hipster I Pets

4.8 (96)

3 Bedrooms • 6 Guests

$219 avg/night

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

Eclectic Escape:Disney Proximity

4.8 (25)

5 Bedrooms • 10 Guests

$422 avg/night

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

Adorable 1-bedroom right on the bike trail

Luxury Room + Bonus Area! Universal Disney

5.0 (20)

1 Bedroom • 4 Guests

Available on

United States Florida Orlando vacation rental compare prices direct by owner 1417513

Disney's Dream 1 - Orlando - FL

5.0 (7)

1 Bedroom • 2 Guests

Available on

United States Florida Clermont vacation rental compare prices direct by owner 2050261

Beautiful and Quaint Home Close to Attractions

5.0 (4)

3 Bedrooms • 8 Guests

Available on

United States Florida Winter Garden vacation rental compare prices direct by owner 24641447

Stylish Bungalow • 3 Min to Downtown • Office Nook

5.0 (12)

2 Bedrooms • 2 Guests

Available on

United States Florida Winter Garden vacation rental compare prices direct by owner 33132746

Winter Garden guest suite

5.0 (27)

1 Bedroom • 2 Guests

$131 avg/night

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