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Maitland, FL Holiday Rentals & Apartments
Holiday Rentals
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Florida (FL)
Central Florida
Maitland, FL Holiday Rentals & Apartments
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Internet or Wifi (49)
Air Conditioning (48)
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Kid friendly (43)
Pet friendly (19)
Elder access (3)
Wheelchair access (0)
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Holiday Rental House (33)
Condominium/Apartment (18)
Cabin Holiday Rental (0)
Private Room (0)
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Private Chef (0)
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Distance from
5 km
Audubon Center for Birds of Prey
Lake Lily Park
Maitland Art Center
The Holocaust Memorial Resource and Education Center
Maitland Community Park
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51 rentals
in Maitland.
Casa Bella
96 reviews
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 8
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Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Casa Feliz
1 review
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Casa Jardin
Holiday Rental House
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3 bedrooms
6 bathrooms
Sleeps 6
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Hotel in Orlando Maitland
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Hidden Gem, New build on Lake
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Modern Lake Front Casita near Winter Park!
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Cheerful 4 Bedroom with Herb Garden, A Side
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 8
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Large living area, tropical backyard with swimming pool & covered back porch
8 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
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Warm and Inviting. Ideally located, 3BR/2BA Home
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Lakewood Luxury 3/2 Home with Sunroom plus Fenced Yard and Covered Patio
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
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Temporary living that feels like home where you can relax and be yourself.
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
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Affordable, convenient and private family space
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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The following properties within 32 kms of Maitland match all your filters:
Stylish Boutique Guest house in Historic Winter Park.
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Sunset Cove Luxury 2BR/2BA Condo Winter Park! FREE GARAGE, Wi-Fi
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 5
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New Renovated House Near Everything
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
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Fern Park House w/ Pool: New Patio & Fire Pit!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Sweet Sunshine house is available now!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Peaceful Retreat #1 -2B /2B Apartment
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 8
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Winter Park charm. Close to Park Ave
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Mid Century Luxury, 1 block from Park Ave (#3)
2 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Sunshine Escape Guesthouse ☀
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Winter Park Oasis
9 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Mid Century Luxury, 1 block from Park Ave (#2)
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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A Gardeners Cottage Home Becomes Your Sanctuary
1 review
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Winter Park Oasis
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 8
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2 bedroom 2 bathroom
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Cozy Comfort Just 2 Blocks From Park Ave!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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As seen on
Stylish Boutique Guest House
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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2 bedroom 2 bathroom
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Orlando Area Vacation Rental ~ 21 Mi to Disney!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Light, Bright and Full of Delight! 2 Blocks to Park Ave
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Three Blocks to Park Ave, 2 Blocks to WP Village!!!
1 review
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Charming 2BR/2BA Winter Park Cottage, steps from Park Ave
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Walk The Downtown Village of Winter Park!!!
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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3brdrm home near WinterPark and Downtown Orlando
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 8
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Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Cozy Comfort In The Heart of Winter Park!
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Luxury Living Just 3 Blocks From Park Ave!!!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Winter Park Retreat
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Comfy Home in Winter Park, can accommodate up 6 guests!
6 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Orlando Poolside Oasis
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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3bdrm entire home near winter park and Downtown Orlando!
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 8
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Charming Heated Pool Home - Altamonte Springs
2 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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You're Pampered Here - Just 3 Blocks From Park Avenue!
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 6
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Charming and Cozy Pool home Altamonte Springs
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Fully renovated 4-bedroom,2-bathroom single family-15 mins from downtown Orlando
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Frequently Asked Questions about Maitland
Do any holiday rentals in Maitland have a pool?
Yes, here are some popular holiday rentals in Maitland that have a pool:
Casa Bella
Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog
Casa Feliz
See all holiday rentals with a pool in Maitland on Tripadvisor
Do any holiday rentals in Maitland have internet access?
Yes, here are some popular holiday rentals in Maitland that have internet access:
Casa Bella
Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog
Casa Feliz
See all holiday rentals in Maitland on Tripadvisor
What are the best pet friendly rentals in Maitland?
The best pet friendly rentals in Maitland are:
Casa Bella
Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog
Lakewood Luxury 3/2 Home with Sunroom plus Fenced Yard and Covered Patio
See all pet friendly holiday rentals in Maitland on Tripadvisor
What are some great rentals in Maitland that are kid friendly?
Some of the most popular kid friendly rentals in Maitland are:
Casa Bella
Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog
Casa Feliz
See all kid friendly holiday rentals in Maitland on Tripadvisor
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