
Windermere long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Windermere. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Windermere are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Windermere
Showing deals for:15 Feb - 15 Mar
Image gallery for Spacious, Private Salt Water Pool/Spa, 15 minutes to Disney & Many Attractions

Spacious, Private Salt Water Pool/Spa, 15 minutes to Disney & Many Attractions
Davenport
Image gallery for Pet-Friendly Townhome Near Disney - Emerald Island Resort

Pet-Friendly Townhome Near Disney - Emerald Island Resort
Kissimmee
Image gallery for Secret Garden Villa | 4BR/3BA Davenport | Private Pool

Secret Garden Villa | 4BR/3BA Davenport | Private Pool
Davenport
Image gallery for Movie MAGIC 7br. Only 8 mi to Disney! Free Resort, Pool heat and BBQ!

Movie MAGIC 7br. Only 8 mi to Disney! Free Resort, Pool heat and BBQ!
Clermont
Image gallery for Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!

Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!
Kissimmee
Image gallery for 4 Bedrm 3.5 Bath Home in Resort Community sleeps 10 Close to Theme Parks

4 Bedrm 3.5 Bath Home in Resort Community sleeps 10 Close to Theme Parks
Davenport
Image gallery for Bright 5BR/3BA Kissimmee Home in Gated Community, Pool View

Bright 5BR/3BA Kissimmee Home in Gated Community, Pool View
Kissimmee
Image gallery for The Ocean's Cove - Free Parking

The Ocean's Cove - Free Parking
Orlando
Image gallery for Minutes to Disney, 5BR+4BA, Private Heated Pool, Resort Access!

Minutes to Disney, 5BR+4BA, Private Heated Pool, Resort Access!
Davenport
Image gallery for Serenity Stay | 3BR/3BA Clermont | Private Pool

Serenity Stay | 3BR/3BA Clermont | Private Pool
Clermont
Image gallery for Spectacular Lake View - Game/Media Room - Vacation Home Close to Disney

Spectacular Lake View - Game/Media Room - Vacation Home Close to Disney
Kissimmee
Image gallery for 588 - Great Family Home near Disney, private pool - Bellavida Resort

588 - Great Family Home near Disney, private pool - Bellavida Resort
Kissimmee
Image gallery for Marvellous Magic 3BR/2BA Kissimmee Townhome, Near Disney

Marvellous Magic 3BR/2BA Kissimmee Townhome, Near Disney
Kissimmee
Image gallery for Heated Pool + Movie Room | Champions Gate | 5BD

Heated Pool + Movie Room | Champions Gate | 5BD
Davenport
Image gallery for House by the Mouse-Lux one Story Home; 3 miles to Disney, Private Pool and spa

House by the Mouse-Lux one Story Home; 3 miles to Disney, Private Pool and spa
Kissimmee
Image gallery for 4BR Storey Lake Villa w/ Pool View, Near Disney

4BR Storey Lake Villa w/ Pool View, Near Disney
Kissimmee
Image gallery for 5BR Poolside Retreat

5BR Poolside Retreat
Kissimmee
Image gallery for 3157- Great Family Home near Disney, private pool, Storey Lake Resort.

3157- Great Family Home near Disney, private pool, Storey Lake Resort.
Kissimmee
Image gallery for Fabulous 5BR Townhome: Pet Friendly - Private Pool - Windsor Island

Fabulous 5BR Townhome: Pet Friendly - Private Pool - Windsor Island
Kissimmee
Image gallery for Downtown Orlando “Birdhouse”

Downtown Orlando “Birdhouse”
Orlando
Image gallery for 4869 - Great Family Home near Disney (private pool) Storey Lake Resort.

4869 - Great Family Home near Disney (private pool) Storey Lake Resort.
Kissimmee
Image gallery for Elegant penthouse with ample space – the perfect place to connect and relax!

Elegant penthouse with ample space – the perfect place to connect and relax!
Orlando
Image gallery for Paradise Villa, No rear neighbors, Minutes from Disney

Paradise Villa, No rear neighbors, Minutes from Disney
Kissimmee
Image gallery for Harry Potter Villa - 10 Mins to Disney

Harry Potter Villa - 10 Mins to Disney
Kissimmee
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Windermere
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Windermere Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Windermere come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Windermere
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Windermere with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Windermere
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Windermere with flexible cancellation policies.