This City Knows - Vacation Rentals in Windermere

McAllisters on 8th From US $51
         

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9.4 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Stay Safe & Central – Your Cozy B&B Near Florida Road! From US $109
         

New
Bed & Breakfast
  • Air Conditioner
  • Pool
  • Security/Safety
806 2SIX2 Florida Road From US $86
         

New
Apartment
  • Parking
  • TV
  • Balcony/Terrace
603 2SIX2 Florida Road From US $80
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pool
Stunning Slick 902 Florida Road From US $77
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Windermere

Over 67+ Luxury Places to Stay in or Near Windermere
TheRestInn @ 2Six2 Florida From US $222
         

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8.6 (366 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Glorystar 2Six2 Florida Road From US $128
         

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9.0 (899 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Zet On 9TH Avenue From US $115
         

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8.7 (88 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Sensitively restored spacious apartment From US $109
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Quarters Hotel From US $105
         

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8.3 (112 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
2SIX2 On Florida Road, Modern Lifestyle apartment 802 From US $99
         

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9.1 (56 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Lalala Guesthouse From US $91
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Crestholme From US $90
         

New
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Windermere

Over 31+ Top-Rated Vacation Rentals with a Pool in or Near Windermere
Hampton Collection - Contemporary 3 Sleeper Apartment with Pool From US $69
         

603 2SIX2 Florida Road From US $74
         

9.3 (19 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
2SIX2, FLORIDA ROAD From US $75
         

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9.2 (197 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Hampton Collection - Stylish 3 Sleeper Apartment with Pool From US $75
         

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9.2 (104 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Hampton Collection - 2 Sleeper Studio Apartment with Pool From US $56
         

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9.1 (40 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Florida Road LUX Apartment From US $70
         

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9.1 (35 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
806 2SIX2 Florida Road From US $66
         

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9.1 (20 Reviews)
Apartment
  • Parking
  • Pool
  • Accessibility
Holland House B&B From US $70
         

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9.0 (230 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Windermere

Over 4+ Pet-Friendly Vacation Rentals in or Near Windermere
Dior-X Manor From US $72
         

6.8 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
JH Guest house From US $25
         

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5.2 (46 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Palm Terrace Guesthouse From US $80
         

New
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Kings Park Lodge From US $26
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Windermere

Over 8+ Large Vacation Homes & Villas in or Near Windermere
McAllisters on 8th From US $52
         

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8.9 (286 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Madeline Grove Bed & Breakfast From US $52
         

8.3 (827 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Bentley House From US $36
         

8.2 (53 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Esperamos From US $47
         

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7.9 (603 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Florida Palms Guesthouse From US $49
         

7.2 (91 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Sommersby Bed & Breakfast From US $66
         

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6.7 (83 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Tekweni Backpackers From US $46
         

5.6 (49 Reviews)
Cabin
  • Parking
  • Pool
  • TV
Prime Hotel From US $38
         

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7.2 (1612 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Windermere Vacation Rentals and Airbnb Places to Stay Under $200

Over 37+ Windermere Vacation Rentals and Airbnb Places to Stay Under $200
HMT Luxury Holiday Apartment From US $68
         

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10.0 (1 Review)
Apartment
  • Parking
  • View
  • Balcony/Terrace
Madeline Grove B&B From US $56
         

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8.4 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Vibrant 603 on Florida Road From US $82
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV
Rosetta Cottage From US $35
         

9.8 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Accessibility
Concord Christian Guesthouse From US $52
         

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8.0 (32 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
601@2SIX2 Florida Road From US $81
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
707@2SIX2 Florida Road From US $68
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV

About Windermere Vacation Rentals

With more than 76 Windermere vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Thiscityknows and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windermere.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Thiscityknows Windermere, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windermere. Places to stay near Windermere are 342.25 ft² on average, with prices averaging $71 a night.

Thiscityknows makes it easy and safe to find and compare vacation rentals in Windermere with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windermere

Type Count
Holiday Apartments 34
Vacation Homes 17
Hotels with Suites 13
B&B 9
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windermere

Pro Tip: Thiscityknows makes it easy to compare the best listings on Thiscityknows homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thiscityknows homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windermere.

Weather in Windermere

View the weather forecast for Windermere before booking your Windermere Vacation Rentals to confirm your best time to go.

December - February
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March - May
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June - August
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Windermere Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Windermere?
How many vacation rentals are available in Windermere?

Currently, the total number of properties listed in 2026 is over 76 in the Windermere area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windermere.