Holiday Homes in Maitland
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51 rentals in Maitland.
Casa Bella
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Feliz
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Jardin
Holiday Rental House
3 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
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Hotel in Orlando Maitland
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hidden Gem, New build on Lake
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Lake Front Casita near Winter Park!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cheerful 4 Bedroom with Herb Garden, A Side
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Warm and Inviting. Ideally located, 3BR/2BA Home
Holiday Rental House
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
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Temporary living that feels like home where you can relax and be yourself.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Affordable, convenient and private family space
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Renovated House Near Everything
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Fern Park House w/ Pool: New Patio & Fire Pit!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sweet Sunshine house is available now!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Peaceful Retreat #1 -2B /2B Apartment
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Winter Park charm. Close to Park Ave
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mid Century Luxury, 1 block from Park Ave (#3)
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cute Guest House In Winter Park Minutes From Downtown in Car
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sunshine Escape Guesthouse ☀
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Winter Park Oasis
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mid Century Luxury, 1 block from Park Ave (#2)
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Gardeners Cottage Home Becomes Your Sanctuary
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Winter Park Oasis
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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2 bedroom 2 bathroom
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Comfort Just 2 Blocks From Park Ave!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stylish Boutique Guest House
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2 bedroom 2 bathroom
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Orlando Area Vacation Rental ~ 21 Mi to Disney!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Light, Bright and Full of Delight! 2 Blocks to Park Ave
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Three Blocks to Park Ave, 2 Blocks to WP Village!!!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 2BR/2BA Winter Park Cottage, steps from Park Ave
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk The Downtown Village of Winter Park!!!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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3brdrm home near WinterPark and Downtown Orlando
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Comfort In The Heart of Winter Park!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Living Just 3 Blocks From Park Ave!!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Winter Park Retreat
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Comfy Home in Winter Park, can accommodate up 6 guests!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A comfortable home close to the city, yet tucked away from the noise.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Orlando Poolside Oasis
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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3bdrm entire home near winter park and Downtown Orlando!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Charming Heated Pool Home - Altamonte Springs
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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You're Pampered Here - Just 3 Blocks From Park Avenue!
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming and Cozy Pool home Altamonte Springs
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fully renovated 4-bedroom,2-bathroom single family-15 mins from downtown Orlando
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 51
Frequently Asked Questions about Maitland
- 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
- 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
- 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
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