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Lakes Resorts - Vacation Rentals in Longwood

Resort Like house, 4 bedrooms, 3 bathrooms From US $273
         

8.4 (5 Reviews)
House
Resort Like house, 4 bedrooms, 3 bathrooms
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Places to Stay in Longwood

Over 64+ Luxury Places to Stay in or Near Longwood
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub From US $1,637
         

New
House
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
  • Air Conditioner
  • Parking
  • Pool

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Luxurious Home, Beautiful Views, Gated Community, min. 6 mo. rental, May -Nov. From US $808
         

New
House
Luxurious Home, Beautiful Views, Gated Community, min. 6 mo. rental, May -Nov.
  • Air Conditioner
  • Parking
  • Pool

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Recharge @ Timberland Lodge: Pool Hottub Sauna From US $588
         

10.0 (12 Reviews)
House
Recharge @ Timberland Lodge: Pool Hottub Sauna
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tropical Oasis - Heated Luxury Pool - Game Room From US $556
         

10.0 (20 Reviews)
House
Tropical Oasis - Heated Luxury Pool - Game Room
  • Air Conditioner
  • Parking
  • Pet Friendly

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Private 4-Bedroom home with pool! The luxury neighborhood of Markham Woods. From US $526
         

9.2 (5 Reviews)
House
Private 4-Bedroom home with pool! The luxury neighborhood of Markham Woods.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Themed 6BR Home! Prime Location! Very Spacious! Close to Disney and Universal! From US $510
         

New
House
Themed 6BR Home! Prime Location! Very Spacious! Close to Disney and Universal!
  • Air Conditioner
  • Parking
  • Pet Friendly

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WHOLE HOUSE Near Universal & Seaworld From US $505
         

10.0 (3 Reviews)
House
WHOLE HOUSE Near Universal & Seaworld
  • Air Conditioner
  • Parking
  • Pet Friendly

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Private Outdoor Oasis with Pool Home in Longwood! From US $483
         

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New
House
Private Outdoor Oasis with Pool Home in Longwood!
  • Parking
  • Pool
  • Accessibility

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Top-Rated Vacation Rentals with a Pool in Longwood

Over 17+ Top-Rated Vacation Rentals with a Pool in or Near Longwood
Relax by the pool at this retreat near parks, kayaking, and downtown. From US $92
         

10.0 (179 Reviews)
House
Relax by the pool at this retreat near parks, kayaking, and downtown.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious Family House with Private Pool in Central Florida From US $287
         

10.0 (32 Reviews)
House
Spacious Family House with Private Pool in Central Florida
  • Air Conditioner
  • Parking
  • Pool

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This Charming House with an outdoor pool, 3 bedrooms, 2 full baths. From US $327
         

10.0 (8 Reviews)
House
This Charming House with an outdoor pool, 3 bedrooms, 2 full baths.
  • Air Conditioner
  • Parking
  • Pool

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Private Outdoor Oasis w/Pool: Home in Longwood! From US $422
         

9.6 (4 Reviews)
House
Private Outdoor Oasis w/Pool: Home in Longwood!
  • Air Conditioner
  • Parking
  • Pool

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2BR Dog-Friendly Oasis w/Shared Pool & Patio
New
From US $249
         

New
House
2BR Dog-Friendly Oasis w/Shared Pool & Patio
  • Air Conditioner
  • Pet Friendly
  • Pool

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Sun-filled oasis with furnished patio, shared pool, & fire pit - dog-friendly From US $243
         

8.8 (6 Reviews)
House
Sun-filled oasis with furnished patio, shared pool, & fire pit - dog-friendly
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  • Parking
  • Pet Friendly

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Your Oasis Home From US $259
         

7.2 (5 Reviews)
House
Your Oasis Home
  • Air Conditioner
  • Parking
  • Pool

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Family Friendly House - 45min from Orlando Theme Parks and the Beach! From US $407
         

5.0 (12 Reviews)
House
Family Friendly House - 45min from Orlando Theme Parks and the Beach!
  • Air Conditioner
  • Pool
  • TV

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Pet-Friendly Vacation Rentals in Longwood

Over 18+ Pet-Friendly Vacation Rentals in or Near Longwood
Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games From US $240
         

9.4 (14 Reviews)
House
Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games
  • Air Conditioner
  • Parking
  • Pet Friendly

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Longwood Private Suite - Near Orlando - Modern, Private Entrance, Fast WiFi From US $102
         

New
House
Longwood Private Suite - Near Orlando - Modern, Private Entrance, Fast WiFi
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  • Parking
  • Pet Friendly

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The Frogs Castle From US $232
         

8.8 (64 Reviews)
House
The Frogs Castle
  • Air Conditioner
  • Parking
  • Pet Friendly

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3-bedroom Peaceful Longwood Home – Minutes to Attractions - Netflix - LOCATION
New
From US $274
         

New
House
3-bedroom Peaceful Longwood Home – Minutes to Attractions - Netflix - LOCATION
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy Studio – Minutes to Wekiva, Disney & downtown Orl - Netflix - XL parking
New
From US $108
         

New
Apartment
Cozy Studio – Minutes to Wekiva, Disney & downtown Orl - Netflix - XL parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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Modern Luxury Retreat - Bright, Cozy & Family-Ready near Orlando, FL From US $499
         

10.0 (1 Review)
House
Modern Luxury Retreat - Bright, Cozy & Family-Ready near Orlando, FL
  • Air Conditioner
  • Parking
  • Pet Friendly

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Florida Retreat w/ Pool, Near Walt Disney World! From US $245
         

4.8 (19 Reviews)
House
Florida Retreat w/ Pool, Near Walt Disney World!
  • Air Conditioner
  • Pet Friendly
  • Pool

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Cozy 3 Bedroom Home, Great location!!!!! From US $175
         

4.8 (14 Reviews)
House
Cozy 3 Bedroom Home, Great location!!!!!
  • Air Conditioner
  • Pet Friendly
  • TV

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Large Vacation Homes & Villas in Longwood

Over 5+ Large Vacation Homes & Villas in or Near Longwood
Fire Pit + Private Yard: Family Home in Longwood! From US $225
         

9.8 (8 Reviews)
House
Fire Pit + Private Yard: Family Home in Longwood!
  • Air Conditioner
  • Parking
  • TV

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Fire Pit and Private Yard Family Home in Longwood! From US $189
         

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10.0 (1 Review)
House
Fire Pit and Private Yard Family Home in Longwood!
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  • Accessibility
  • Security/Safety

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Spacious and relaxing Home - North Of Orlando In Longwood, Florida From US $364
         

9.4 (32 Reviews)
House
Spacious and relaxing Home - North Of Orlando In Longwood, Florida
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  • Parking
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Spacious 5-bedroom house with WiFi, AC in charming Longwood From US $269
         

New
House
Spacious 5-bedroom house with WiFi, AC in charming Longwood
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy House in Historic Longwood FL From US $199
         

2.0 (1 Review)
House
Cozy House in Historic Longwood FL
  • Air Conditioner
  • Parking
  • Pet Friendly

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Longwood Varoom and Airbnb Places to Stay Under $200

Over 16+ Longwood Varoom and Airbnb Places to Stay Under $200
Spacious Central Florida Home Family Friendly! From US $165
         

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10.0 (1 Review)
House
Spacious Central Florida Home Family Friendly!
  • Parking
  • View
  • Accessibility

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Tiny Hidden Cottage From US $153
         

9.2 (59 Reviews)
Cottage
Tiny Hidden Cottage
  • Air Conditioner
  • Parking
  • TV

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6 months min From US $139
         

9.0 (4 Reviews)
Condo
6 months min
  • Air Conditioner
  • Parking
  • TV

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Luxury 2 room near Disney From US $138
         

New
House
Luxury 2 room near Disney
  • Air Conditioner
  • Security/Safety
  • Child Friendly

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"Urban Oasis: A Tropical Hideout in the Heart of Orlando's Vibrant Suburbs" From US $157
         

10.0 (1 Review)
Cottage
"Urban Oasis: A Tropical Hideout in the Heart of Orlando's Vibrant Suburbs"
  • Air Conditioner
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  • TV

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Enjoy a tailor made experience at this centrally-located place. From US $187
         

9.6 (5 Reviews)
House
Enjoy a tailor made experience at this centrally-located place.
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Beautiful back drop for your vacation. From US $134
         

9.0 (2 Reviews)
House
Beautiful back drop for your vacation.
  • Air Conditioner
  • Parking
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Charming 2-bedroom house near Wekiwa Springs State Park, pet friendly. From US $185
         

New
House
Charming 2-bedroom house near Wekiwa Springs State Park, pet friendly.
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Instantly Bookable Vacation Homes in Longwood

Over 13+ Instantly Bookable Vacation Homes in or Near Longwood
Lakefront Home Where You Can Retreat And Relax From US $242
         

9.8 (19 Reviews)
House
Lakefront Home Where You Can Retreat And Relax
  • Air Conditioner
  • Parking
  • TV

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Downtown Historic Longwood steps to City park & SunRail From US $285
         

10.0 (6 Reviews)
House
Downtown Historic Longwood steps to City park & SunRail
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

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WHEELCHAIR ACCESSIBLE 3 Bedroom 2 Bathroom Home From US $243
         

10.0 (5 Reviews)
House
WHEELCHAIR ACCESSIBLE 3 Bedroom 2 Bathroom Home
  • Air Conditioner
  • Parking
  • TV

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The lakefront Brantley House From US $282
         

10.0 (4 Reviews)
House
The lakefront Brantley House
  • Air Conditioner
  • Parking
  • TV

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Spacious Central Florida Home: Family Friendly! From US $272
         

9.8 (27 Reviews)
House
Spacious Central Florida Home: Family Friendly!
  • Air Conditioner
  • Parking
  • TV

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Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida From US $420
         

9.6 (17 Reviews)
Ski Chalet
Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Peaceful family retreat-centrally located for attraction options! From US $231
         

8.8 (5 Reviews)
House
Peaceful family retreat-centrally located for attraction options!
  • Air Conditioner
  • Parking
  • TV

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A stunning retreat on a luxurious 2 acre estate
New
From US $249
         

New
House
A stunning retreat on a luxurious 2 acre estate
  • Air Conditioner
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  • TV

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About Longwood Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Lakesresorts Longwood, 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 Longwood. Places to stay near Longwood are 75.35 ft² on average, with prices averaging $273 a night.

Lakesresorts makes it easy and safe to find and compare vacation rentals in Longwood 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 Longwood

Type Count
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Longwood

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

Weather in Longwood

View the weather forecast for Longwood before booking your Longwood 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

Top Attractions Around Longwood, FL

Lakesresorts offers a large selection of top attractions around Longwood. Research things to do on your vacation before you visit Longwood.


Boombah-Soldiers Creek Park The Legacy at Alaqua Lakes Rebounderz of Longwood Big Tree Park Aiguille Rock Climbing Center The Trophy Club Of Orlando Alaqua Country Club Diamond Player's Club - Wekiva SeaWorld® Orlando Universal Orlando ResortTM Universal Studios FloridaTM Orange County Convention Center Florida Mall Orlando International Premium Outlets Amway Center Camping World Stadium Holy Land Experience The Wizarding World of Harry PotterTM University of Central Florida Aquatica

Other Places to Stay Near Longwood, FL


North Orlando 540 Properties Aiguille Rock Climbing Center 143 Properties Rebounderz of Longwood 130 Properties The Trophy Club Of Orlando 111 Properties Big Tree Park 92 Properties Boombah-Soldiers Creek Park 86 Properties Diamond Player's Club - Wekiva 73 Properties The Legacy at Alaqua Lakes 56 Properties Alaqua Country Club 38 Properties Wekiva Springs 36 Properties