Windermere Vacation Rentals

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Vacation Rentals in Windermere

The Berkley, Orlando

8545 W. Irlo Bronson Highway Kissimmee FL

$138 nightly

$155 total

Dec 14 - Dec 15

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at The Berkley, Orlando in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center.

Pool

Hot Tub

Formosa Valley Resort by UNE Homes

Formosa Vly Pl Kissimmee FL

$476 nightly

$529 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at Formosa Valley Resort by UNE Homes in Kissimmee, you'll be a 3-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort.

Pool

Kitchen

Marriott's Sabal Palms

8805 World Center Dr Orlando FL

$255 nightly

$287 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

Located in Orlando, Marriott's Sabal Palms is within a 15-minute drive of Disney's Hollywood Studios® and Aquatica.

Pool

Hot Tub

Magic Retreat Orlando

Davenport FL

$307 nightly

$339 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Flamingo Crossings Town Center and Highland Reserve Golf Club.

Pool

Hot Tub

Doppio Westside

2470 Santorini Drive Davenport FL

$376 nightly

$426 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at Doppio Westside in Four Corners, you'll be within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center.

Pool

Kitchen

Vista Cay Resort by Casiola Vacation Homes

4874 Cayview Ave Orlando FL

$400 nightly

$450 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

When you stay at Vista Cay Resort by Casiola Vacation Homes in Orlando, you'll be connected to the convention center, within a 5-minute drive of Orange County Convention Center and Aquatica.

Pool

Hot Tub

The Rose Nest near Disney at Champions Gate!

Davenport FL

With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club.

Pool

Hot Tub

Fantastic Stunning New Designer Townhouse!!

Kissimmee FL

With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town.

Pool

Hot Tub

Experience Luxury in Your 11 En-Suites Mansion

Orlando FL

With a stay at this vacation home in Orlando, you'll be a 5-minute drive from Aquatica and 6 minutes from Orange County Convention Center.

Pool

Hot Tub

Westgate Blue Tree

12007 Cypress Run Dr Orlando FL

$281 nightly

$325 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

With a stay at this vacation home in Orlando, you'll be within a 5-minute drive of Disney Springs™ and Orlando Vineland Premium Outlets.

Pool

Kitchen

Beautiful 9-bedroom Windsor house near Disney

Kissimmee FL

With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center.

Summerville Vacation Homes by Columbia Management

2621 Sunrise Shores Drive Kissimmee FL

A stay at Summerville Vacation Homes by Columbia Management places you in the heart of Kissimmee, within a 10-minute drive of Walt Disney World® Resort and Old Town.

Pool

Hot Tub

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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.