Best price vacation rentals in Maitland, FL, USA • 150 Listings
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Maitland, FL, USA Vacation Rentals | 

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5.0 (200)
The Blue Heron - Lakefront Getaway
Up to 4 guests
Airbnb$89
Vrbo$101
Average Nightly Rate
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5.0 (148)
Just 3 blocks to Park Ave shops / restaurants, 2 from Winter Park Village!
Up to 6 guests
Airbnb$171
Vrbo$189
Average Nightly Rate
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5.0 (389)
The Ritz - Just because it’s a tiny house, doesn't mean you have to skimp on ...
Up to 5 guests
Airbnb$103
Vrbo$115
Average Nightly Rate
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5.0 (369)
The Cottage - Quaint tiny home filled with charm!
Up to 3 guests
Airbnb$89
Vrbo$120
Average Nightly Rate
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5.0 (201)
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths
Up to 4 guests
Airbnb$130
Vrbo$130
Average Nightly Rate
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5.0 (122)
Cozy comfort in the heart of the winter park!
Up to 4 guests
Vrbo$109
Airbnb$114
Average Nightly Rate
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5.0 (363)
The Venice - Trendy tiny home with panoramic views of beautiful Lake Fairview!
Up to 3 guests
Airbnb$103
Vrbo$113
Average Nightly Rate

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5.0 (217)
The Universal - Stylish tiny home perfect for a family vacation
Up to 4 guests
Airbnb$99
Vrbo$112
Average Nightly Rate
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5.0 (70)
Beautiful Peaceful fenced yard home !
Up to 10 guests
Airbnb$248
Vrbo$277
Average Nightly Rate

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5.0 (221)
The View - Waterfront tiny home with incredible panoramic views
Up to 4 guests
Airbnb$109
Vrbo$113
Average Nightly Rate
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5.0 (148)
WeLive Winter Park / Spacious Enclave W/ Patio!
Up to 10 guests
Vrbo$182
Airbnb$190
Average Nightly Rate
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5.0 (196)
The Galaxy - A tiny house that is out of this world!
Up to 4 guests
Airbnb$98
Vrbo$99
Average Nightly Rate
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5.0 (283)
The Retreat - Adorable tiny home steps from the lake!
Up to 4 guests
Airbnb$89
Vrbo$96
Average Nightly Rate
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5.0 (69)
Magnificent Lakefront House • Swim/Fish/Relax • EV Charger
Up to 12 guests
Airbnb$572
Vrbo$572
Average Nightly Rate
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5.0 (202)
🧡 Unique 6/3, Pool, Pergola, Movie/Game Room, UCF, Disney, Beaches, 5⭐
Up to 20 guests
Vrbo$304
Airbnb$317
Average Nightly Rate
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5.0 (166)
ELEGANT ESTATE VACATION RESORT HOME "THE OLIVIA"
Up to 12 guests
Airbnb$138
Vrbo$149
Average Nightly Rate
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5.0 (174)
Winter Park charm. Close to Park Ave
Up to 4 guests
Airbnb$114
Vrbo$119
Average Nightly Rate
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5.0 (92)
Resort Like Private Pool Waterfront Retreat 4/2 Home in East Orlando Florida
Up to 8 guests
Airbnb$205
Vrbo$212
Average Nightly Rate
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4.9 (53)
Mid Century Modern Cottage in the heart of Winter Park
Up to 5 guests
Airbnb$117
Vrbo$125
Average Nightly Rate
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4.9 (143)
Large living area, tropical backyard with swimming pool & covered back porch
Up to 5 guests
Airbnb$160
Vrbo$170
Average Nightly Rate
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4.9 (38)
The Swan - Luxury tiny home perfect for a lakeside getaway!
Up to 6 guests
Vrbo$103
Airbnb$108
Average Nightly Rate
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4.9 (36)
NEW! 1-Story Apopka House w/ Private Lanai + Pool!
Up to 10 guests
Vrbo$309
Airbnb$321
Average Nightly Rate
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4.9 (8)
Rest, Swim, & Relax at Cozy Lakefront Tiki Bungalow perfect for long-term stays
Up to 6 guests
Airbnb$320
Vrbo$320
Average Nightly Rate
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4.9 (41)
Stroll to Park Avenue from Vintage Lake-View House
Up to 6 guests
Airbnb$240
Vrbo$240
Average Nightly Rate
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4.8 (35)
Orlando Area 4BR/2BA Home w/Jacuzzi & New Communal pool Disney Universal Daytona
Up to 10 guests
Airbnb$151
Vrbo$151
Average Nightly Rate
  1. United States
  2. Florida
  3. Maitland Vacation Rental Price Comparison

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