Winter Garden Cottages

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Cottages in Winter Garden

Historic Tremain Cottages

619 N Tremain St Mount Dora FL

$219 nightly

$243 total

Oct 21 - Oct 22

Total with taxes and fees

With a stay at Historic Tremain Cottages in Mount Dora, you'll be just steps from Mount Dora Community Building and Donnelly Park.

Kitchen

Washer

Encore Swanky

411 Lasso Drive Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.

Pool

Kitchen

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Mount Dora FL

$242 nightly

$266 total

Nov 13 - Nov 14

Total with taxes and fees

With a stay at this cottage in Mount Dora, you'll be within a 5-minute drive of Lake Gertrude and The Donnelly House.

Kitchen

Washer

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Orlando FL

$296 nightly

$329 total

Nov 4 - Nov 5

Total with taxes and fees

With a stay at this cottage in Orlando (College Park), you'll be within a 5-minute drive of Kia Center and Camping World Stadium.

Kitchen

Washer

Enchanted Cottage with Pool and Mini-Golf Near Disney

Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets.

Pool

Hot Tub

Cozy Mount Dora Cottage /Walk Downtown/ Pet Friendly / Fenced Yard

Mount Dora FL

A stay at this cottage places you in the heart of Mount Dora, within a 5-minute walk of Donnelly Park and Mount Dora Community Building.

Kitchen

Washer

Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Lake Mary FL

$257 nightly

$284 total

Nov 3 - Nov 4

Total with taxes and fees

With a stay at this cottage in Lake Mary, you'll be within a 5-minute drive of Lake Mary Farmer's Market and Spring Hammock Preserve.

Pool

Kitchen

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

Kissimmee FL

$256 nightly

$287 total

Oct 27 - Oct 28

Total with taxes and fees

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town.

Hot Tub

Kitchen

Tiny Hidden Cottage

Longwood FL

With a stay at this cottage in Longwood, you'll be within a 5-minute drive of Altamonte Mall and Cranes Roost Park.

Kitchen

Free WiFi

PRIVATE LAKEFRONT + DOCK Bring your boat, Hot Tub, Kayaks, Paddleboards

Montverde FL

Located in Montverde, this cottage is by the sea, within a 10-minute drive of Ferndale Preserve and Johns Lake.

Hot Tub

Kitchen

Private Lakefront Cottage, Bright, Peaceful, and Perfect for a Relaxing Escape.

Clermont FL

With a stay at this cottage in Clermont, you'll be on the waterfront, just steps from Johns Lake and a 4-minute drive from Sanctuary Ridge Golf Club.

Kitchen

Washer

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

Mt Dora FL

Located in Mount Dora, this cottage is within a 5-minute drive of Lake Gertrude and Lake Dora.

Kitchen

Free WiFi

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.