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Holiday Homes in Maitland

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Bedrooms

Bathrooms

Amenities

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Distinctive Features

Distance from

5 km
51 rentals in Maitland.
Casa Bella, holiday rental in Maitland
Casa Bella, holiday rental in Maitland
Casa Bella, holiday rental 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 in Maitland
Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog, holiday rental in Maitland
Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog, holiday rental in Maitland

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 in Maitland
Casa Feliz, holiday rental in Maitland
Casa Feliz, holiday rental in Maitland

Casa Feliz

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Jardin, holiday rental in Maitland
Casa Jardin, holiday rental in Maitland
Casa Jardin, holiday rental in Maitland

Casa Jardin

Holiday Rental House
3 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
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Hotel in Orlando Maitland, holiday rental in Maitland
Hotel in Orlando Maitland, holiday rental in Maitland
Hotel in Orlando Maitland, holiday rental in Maitland

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 in Maitland
Hidden Gem, New build on Lake, holiday rental in Maitland
Hidden Gem, New build on Lake, holiday rental in Maitland

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 in Maitland
Modern Lake Front Casita near Winter Park!, holiday rental in Maitland
Modern Lake Front Casita near Winter Park!, holiday rental in Maitland

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 in Maitland
Cheerful 4 Bedroom with Herb Garden, A Side, holiday rental in Maitland
Cheerful 4 Bedroom with Herb Garden, A Side, holiday rental in Maitland

Cheerful 4 Bedroom with Herb Garden, A Side

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Large living area, tropical backyard with swimming pool & covered  back porch, holiday rental in Maitland
Large living area, tropical backyard with swimming pool & covered  back porch, holiday rental in Maitland
Large living area, tropical backyard with swimming pool & covered  back porch, holiday rental in Maitland

Large living area, tropical backyard with swimming pool & covered back porch

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Warm and Inviting. Ideally located, 3BR/2BA Home , holiday rental in Maitland
Warm and Inviting. Ideally located, 3BR/2BA Home , holiday rental in Maitland
Warm and Inviting. Ideally located, 3BR/2BA Home , holiday rental in Maitland

Warm and Inviting. Ideally located, 3BR/2BA Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakewood Luxury 3/2 Home with Sunroom plus Fenced Yard and Covered Patio, holiday rental in Maitland
Lakewood Luxury 3/2 Home with Sunroom plus Fenced Yard and Covered Patio, holiday rental in Maitland
Lakewood Luxury 3/2 Home with Sunroom plus Fenced Yard and Covered Patio, holiday rental in Maitland

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 in Maitland
Temporary living that feels like home where you can relax and be yourself., holiday rental in Maitland
Temporary living that feels like home where you can relax and be yourself., holiday rental in Maitland

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, holiday rental in Maitland
Affordable, convenient and private family space, holiday rental in Maitland
Affordable, convenient and private family space, holiday rental in Maitland

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., holiday rental in Maitland
Stylish Boutique Guest house in Historic Winter Park., holiday rental in Maitland
Stylish Boutique Guest house in Historic Winter Park., holiday rental in Maitland

Stylish Boutique Guest house in Historic Winter Park.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sunset Cove Luxury 2BR/2BA  Condo Winter Park! FREE GARAGE, Wi-Fi, holiday rental in Maitland
Sunset Cove Luxury 2BR/2BA  Condo Winter Park! FREE GARAGE, Wi-Fi, holiday rental in Maitland
Sunset Cove Luxury 2BR/2BA  Condo Winter Park! FREE GARAGE, Wi-Fi, holiday rental in Maitland

Sunset Cove Luxury 2BR/2BA Condo Winter Park! FREE GARAGE, Wi-Fi

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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New Renovated House Near Everything, holiday rental in Maitland
New Renovated House Near Everything, holiday rental in Maitland
New Renovated House Near Everything, holiday rental in Maitland

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 in Maitland
Fern Park House w/ Pool: New Patio & Fire Pit!, holiday rental in Maitland
Fern Park House w/ Pool: New Patio & Fire Pit!, holiday rental in Maitland

Fern Park House w/ Pool: New Patio & Fire Pit!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sweet Sunshine house is available now!, holiday rental in Maitland
Sweet Sunshine house is available now!, holiday rental in Maitland
Sweet Sunshine house is available now!, holiday rental in Maitland

Sweet Sunshine house is available now!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Peaceful Retreat #1    -2B /2B Apartment, holiday rental in Maitland
Peaceful Retreat #1    -2B /2B Apartment, holiday rental in Maitland
Peaceful Retreat #1    -2B /2B Apartment, holiday rental in Maitland

Peaceful Retreat #1 -2B /2B Apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Winter Park charm. Close to Park Ave, holiday rental in Maitland
Winter Park charm. Close to Park Ave, holiday rental in Maitland
Winter Park charm. Close to Park Ave, holiday rental in Maitland

Winter Park charm. Close to Park Ave

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Mid Century Luxury, 1 block from Park Ave (#3), holiday rental in Maitland
Mid Century Luxury, 1 block from Park Ave (#3), holiday rental in Maitland
Mid Century Luxury, 1 block from Park Ave (#3), holiday rental in Maitland

Mid Century Luxury, 1 block from Park Ave (#3)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Sunshine Escape Guesthouse ☀, holiday rental in Maitland
Sunshine Escape Guesthouse ☀, holiday rental in Maitland
Sunshine Escape Guesthouse ☀, holiday rental in Maitland

Sunshine Escape Guesthouse ☀

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Winter Park Oasis, holiday rental in Maitland
Winter Park Oasis, holiday rental in Maitland
Winter Park Oasis, holiday rental in Maitland

Winter Park Oasis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Mid Century Luxury, 1 block from Park Ave (#2), holiday rental in Maitland
Mid Century Luxury, 1 block from Park Ave (#2), holiday rental in Maitland
Mid Century Luxury, 1 block from Park Ave (#2), holiday rental in Maitland

Mid Century Luxury, 1 block from Park Ave (#2)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, holiday rental in Maitland
☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, holiday rental in Maitland
☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, holiday rental in Maitland

☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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A Gardeners Cottage Home Becomes Your Sanctuary, holiday rental in Maitland
A Gardeners Cottage Home Becomes Your Sanctuary, holiday rental in Maitland
A Gardeners Cottage Home Becomes Your Sanctuary, holiday rental in Maitland

A Gardeners Cottage Home Becomes Your Sanctuary

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Winter Park Oasis, holiday rental in Maitland
Winter Park Oasis, holiday rental in Maitland
Winter Park Oasis, holiday rental in Maitland

Winter Park Oasis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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2 bedroom 2 bathroom, holiday rental in Maitland
2 bedroom 2 bathroom, holiday rental in Maitland
2 bedroom 2 bathroom, holiday rental in Maitland

2 bedroom 2 bathroom

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Cozy Comfort Just 2 Blocks From Park Ave!, holiday rental in Maitland
Cozy Comfort Just 2 Blocks From Park Ave!, holiday rental in Maitland
Cozy Comfort Just 2 Blocks From Park Ave!, holiday rental in Maitland

Cozy Comfort Just 2 Blocks From Park Ave!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Stylish Boutique Guest House, holiday rental in Maitland
Stylish Boutique Guest House, holiday rental in Maitland
Stylish Boutique Guest House, holiday rental in Maitland

Stylish Boutique Guest House

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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2 bedroom 2 bathroom, holiday rental in Maitland
2 bedroom 2 bathroom, holiday rental in Maitland
2 bedroom 2 bathroom, holiday rental in Maitland

2 bedroom 2 bathroom

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Orlando Area Vacation Rental ~ 21 Mi to Disney!, holiday rental in Maitland
Orlando Area Vacation Rental ~ 21 Mi to Disney!, holiday rental in Maitland
Orlando Area Vacation Rental ~ 21 Mi to Disney!, holiday rental in Maitland

Orlando Area Vacation Rental ~ 21 Mi to Disney!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Light, Bright and Full of Delight! 2 Blocks to Park Ave, holiday rental in Maitland
Light, Bright and Full of Delight! 2 Blocks to Park Ave, holiday rental in Maitland
Light, Bright and Full of Delight! 2 Blocks to Park Ave, holiday rental in Maitland

Light, Bright and Full of Delight! 2 Blocks to Park Ave

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Three Blocks to Park Ave, 2 Blocks to WP Village!!!, holiday rental in Maitland
Three Blocks to Park Ave, 2 Blocks to WP Village!!!, holiday rental in Maitland
Three Blocks to Park Ave, 2 Blocks to WP Village!!!, holiday rental in Maitland

Three Blocks to Park Ave, 2 Blocks to WP Village!!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming 2BR/2BA Winter Park Cottage, steps from Park Ave, holiday rental in Maitland
Charming 2BR/2BA Winter Park Cottage, steps from Park Ave, holiday rental in Maitland
Charming 2BR/2BA Winter Park Cottage, steps from Park Ave, holiday rental in Maitland

Charming 2BR/2BA Winter Park Cottage, steps from Park Ave

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Walk The Downtown Village of Winter Park!!!, holiday rental in Maitland
Walk The Downtown Village of Winter Park!!!, holiday rental in Maitland
Walk The Downtown Village of Winter Park!!!, holiday rental in Maitland

Walk The Downtown Village of Winter Park!!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!, holiday rental in Maitland
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!, holiday rental in Maitland
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!, holiday rental in Maitland

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
More info
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3brdrm home near WinterPark and Downtown Orlando, holiday rental in Maitland
3brdrm home near WinterPark and Downtown Orlando, holiday rental in Maitland
3brdrm home near WinterPark and Downtown Orlando, holiday rental in Maitland

3brdrm home near WinterPark and Downtown Orlando

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!, holiday rental in Maitland
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!, holiday rental in Maitland
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!, holiday rental in Maitland

Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy Comfort In The Heart of Winter Park!, holiday rental in Maitland
Cozy Comfort In The Heart of Winter Park!, holiday rental in Maitland
Cozy Comfort In The Heart of Winter Park!, holiday rental in Maitland

Cozy Comfort In The Heart of Winter Park!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Luxury Living Just 3 Blocks From Park Ave!!!, holiday rental in Maitland
Luxury Living Just 3 Blocks From Park Ave!!!, holiday rental in Maitland
Luxury Living Just 3 Blocks From Park Ave!!!, holiday rental in Maitland

Luxury Living Just 3 Blocks From Park Ave!!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Winter Park Retreat, holiday rental in Maitland
Winter Park Retreat, holiday rental in Maitland
Winter Park Retreat, holiday rental in Maitland

Winter Park Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Comfy Home in Winter Park, can accommodate up 6 guests!, holiday rental in Maitland
Comfy Home in Winter Park, can accommodate up 6 guests!, holiday rental in Maitland
Comfy Home in Winter Park, can accommodate up 6 guests!, holiday rental in Maitland

Comfy Home in Winter Park, can accommodate up 6 guests!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Orlando Poolside Oasis, holiday rental in Maitland
Orlando Poolside Oasis, holiday rental in Maitland
Orlando Poolside Oasis, holiday rental in Maitland

Orlando Poolside Oasis

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, holiday rental in Maitland
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, holiday rental in Maitland
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, holiday rental in Maitland

Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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3bdrm entire home near winter park and Downtown Orlando!, holiday rental in Maitland
3bdrm entire home near winter park and Downtown Orlando!, holiday rental in Maitland
3bdrm entire home near winter park and Downtown Orlando!, holiday rental in Maitland

3bdrm entire home near winter park and Downtown Orlando!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Charming Heated Pool Home - Altamonte Springs, holiday rental in Maitland
Charming Heated Pool Home - Altamonte Springs, holiday rental in Maitland
Charming Heated Pool Home - Altamonte Springs, holiday rental in Maitland

Charming Heated Pool Home - Altamonte Springs

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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You're Pampered Here - Just 3 Blocks From Park Avenue!, holiday rental in Maitland
You're Pampered Here - Just 3 Blocks From Park Avenue!, holiday rental in Maitland
You're Pampered Here - Just 3 Blocks From Park Avenue!, holiday rental in Maitland

You're Pampered Here - Just 3 Blocks From Park Avenue!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming and Cozy Pool home Altamonte Springs, holiday rental in Maitland
Charming and Cozy Pool home Altamonte Springs, holiday rental in Maitland
Charming and Cozy Pool home Altamonte Springs, holiday rental in Maitland

Charming and Cozy Pool home Altamonte Springs

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Fully renovated 4-bedroom,2-bathroom single family-15 mins from downtown Orlando, holiday rental in Maitland
Fully renovated 4-bedroom,2-bathroom single family-15 mins from downtown Orlando, holiday rental in Maitland
Fully renovated 4-bedroom,2-bathroom single family-15 mins from downtown Orlando, holiday rental in Maitland

Fully renovated 4-bedroom,2-bathroom single family-15 mins from downtown Orlando

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Showing results 1-50 of 51
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