Montgomery Cottages - Vacation Rentals in Orlando

Newly Renovated Hidden Gem From US $119
         

10.0 (98 Reviews)
House
  • Air Conditioner
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The Carriage House at The Judges Chamber From US $267
         

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10.0 (2 Reviews)
House
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Bohemian Home w/Screened Porch, 3 Mi to Lake! From US $873
         

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10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
4 Mi to Dtwn Guthrie: Family Home w/Fire Pit! From US $321
         

Boho 405 - DI Home Rentals From US $161
         

10.0 (71 Reviews)
House
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Oklahoma State University Boone Pickens stadium1.3 miles away. From US $200
         

10.0 (65 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Luxury Places to Stay in Orlando

Over 399+ Luxury Places to Stay in or Near Orlando
OSU 2 Queen Bed Hotel Room 202 From US $1,111
         

3.6 (5 Reviews)
Apartment
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  • Pet Friendly
Hotel 2 Queen Beds Hotel Room 239 Booking From US $1,111
         

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6.4 (12 Reviews)
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OSU 2 Queen Beds Hotel Room 237 Booking From US $1,111
         

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7.7 (6 Reviews)
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Hotel 2 Queen Beds Hotel Room 226 Booking From US $944
         

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7.3 (17 Reviews)
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Hotel 2 Queen Beds Hotel Room 106 Wi-Fi Booking From US $944
         

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6.5 (21 Reviews)
Apartment
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Orlando

Over 49+ Top-Rated Vacation Rentals with a Pool in or Near Orlando
4 Bedroom Campus Condo with Pool From US $348
         

10.0 (24 Reviews)
Condo
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4 Bedroom/4 Bath Condo- 2 Blocks From Campus From US $370
         

9.6 (20 Reviews)
Condo
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  • Pool
Nestled Victorian Historic Area From US $299
         

9.2 (14 Reviews)
House
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  • Pet Friendly
Microtel Inn & Suites by Wyndham Perry From US $102
         

9.1 (96 Reviews)
Hotel
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  • Pet Friendly
SpringHill Suites by Marriott Stillwater From US $152
         

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8.9 (116 Reviews)
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La Quinta Inn & Suites by Wyndham Guthrie From US $115
         

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8.2 (1002 Reviews)
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La Quinta by Wyndham Guthrie From US $132
         

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8.1 (335 Reviews)
Hotel
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  • Pet Friendly
Comfort Inn & Suites Perry I-35 From US $115
         

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8.1 (110 Reviews)
Hotel
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  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in Orlando

Over 135+ Pet-Friendly Vacation Rentals in or Near Orlando
The Ranch Near Boomer Lake From US $316
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bohemian Home w/Screened Porch, 3 Mi to Lake! From US $146
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Security/Safety
Walk to Downtown: Historic Guthrie Home on Mansur From US $171
         

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10.0 (1 Review)
Cottage
  • Air Conditioner
  • Pet Friendly
  • TV
Pet friendly. Blocks to OSU - 0.7mi to BP Stadium! From US $358
         

10.0 (16 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Charming 1-bedroom house in Stillwater From US $186
         

10.0 (5 Reviews)
House
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  • Pet Friendly
Walk to Downtown: Historic Guthrie Home on Mansur From US $169
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Game Day Getaway 2 – Easy Walk to OSU Stadium From US $277
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Orlando on PetFriendly.io

Large Vacation Homes & Villas in Orlando

Over 40+ Large Vacation Homes & Villas in or Near Orlando
The Water House-Sleeps 10-1 Mile to Boone Pickens From US $273
         

.A View of Boone Pickens Stadium and OSU Athletics From US $281
         

;Cowboy's Cottage on Fern From US $223
         

6.0 (1 Review)
House
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  • TV
Cowboys' Home with a Hot Tub From US $299
         

New
House
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  • Child Friendly

Wheelchair Accessible Vacation Homes in Orlando

Over 36+ Wheelchair Accessible Vacation Homes in or Near Orlando
The Atherton Hotel at OSU From US $432
         

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9.7 (82 Reviews)
Hotel
  • Air Conditioner
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  • View
The Atherton Hotel At OSU From US $147
         

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9.8 (536 Reviews)
Hotel
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Hampton Inn & Suites Stillwater From US $134
         

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9.0 (127 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Microtel Inn & Suites By Wyndham Perry From US $90
         

9.2 (954 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express & Suites Stillwater - University Area by IHG From US $162
         

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8.3 (86 Reviews)
Hotel
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  • Designated Smoking Area
Hampton Inn & Suites Stillwater From US $123
         

9.2 (820 Reviews)
Hotel
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La Quinta by Wyndham Stillwater -University Area From US $147
         

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7.9 (231 Reviews)
Hotel
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  • Pet Friendly

Orlando Vacation Rentals and Airbnb Places to Stay Under $200

Over 181+ Orlando Vacation Rentals and Airbnb Places to Stay Under $200
Dominion Gardens and Hotel From US $135
         

9.6 (547 Reviews)
Hotel
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  • TV
Cowboy Luxe - Chic Studio Apartment From US $169
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Wellness Facilities
Pearl's Place - A Historic, Red-Brick Street Gem From US $194
         

Peaceful Boho Retreat Nestled in the Woods – 5 Mins from Downtown From US $167
         

10.0 (4 Reviews)
Cottage
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
‘Legacy Run:’ Guthrie’s Historic Haven Near Shops From US $195
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
1890 House 1-bedroom Log Cabin in Stillwater From US $128
         

10.0 (3 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Orlando

Over 137+ Instantly Bookable Vacation Homes in or Near Orlando
The Gibby | Stilly Retreat with NEW Game Room! From US $385
         

10.0 (29 Reviews)
House
  • Air Conditioner
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  • TV
Luxury Cottage Getaway From US $276
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
2 King Bed OSU Rental House From US $218
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety

About Orlando Vacation Rentals

With more than 408 Orlando vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages 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 Orlando.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Orlando, 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 Orlando. Places to stay near Orlando are 524.26 ft² on average, with prices averaging US $304 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Orlando 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 Orlando

Type Count
Vacation Homes 196
Holiday Apartments 99
Hotels 56
B&B 22
Cottages 14
Cabin Rentals 5
Others 2
Villas 2
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Orlando

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages 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 Orlando.

Weather in Orlando

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Orlando Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 408 in the Orlando area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Orlando.