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Maitland Vacation Rentals

Hotels (3)

B&Bs / Inns (1)

Specialty Lodging (0)

Vacation Rentals (2,616)

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A A ARent 4 Bed Pool Home 2.5 Miles from Disney, Kissimmee
A A ARent 4 Bed Pool Home 2.5 Miles from Disney
    Price: €51/night
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 2
    • Contact Owner
WATER VIEW VILLA, Kissimmee
WATER VIEW VILLA
    Price: €80 - €104/night
  • Bedrooms: 4, sleeps 10
  • Bathrooms: 2
    • Contact Owner
Brand New 4/4 Luxury Home, pool, spa, cable, wifi, Kissimmee
Brand New 4/4 Luxury Home, pool, spa, cable, wifi
    Price: €104 - €139/night €863 - €971/week
  • Bedrooms: 4, sleeps 11
  • Bathrooms: 4
    • Contact Owner
Terra Verde - Modern 5br with lakeview & WiFi, Kissimmee
Terra Verde - Modern 5br with lakeview & WiFi
    Price: €87 - €191/night
  • Bedrooms: 5, sleeps 10
  • Bathrooms: 3
    • Contact Owner
Wonderful Townhome with Splash Pool near Disney!, Kissimmee
Wonderful Townhome with Splash Pool near Disney!
    Price: €62 - €145/night €436 - €1,014/week
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 3
    • Contact Owner
Avalon somewhere special to stay, close to WDW, Kissimmee
Avalon somewhere special to stay, close to WDW
    Price: €866 - €1,247/week
  • Bedrooms: 6, sleeps 14
  • Bathrooms: 4
  • Min stay: 7
    • Contact Owner
3B Townhome Vacation Rental Emerald Island Resort, Kissimmee
3B Townhome Vacation Rental Emerald Island Resort
    Price: €58 - €89/night €405 - €624/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 3
    • Contact Owner
Windsor Hills Spacious 4 bed,wifi, home cinema/den, Kissimmee
Windsor Hills Spacious 4 bed,wifi, home cinema/den
    Price: €897 - €1,212/week
  • Bedrooms: 4, sleeps 10
  • Bathrooms: 5
    • Contact Owner
Beautiful Pool Home Close to Disney & Universal, Kissimmee
Beautiful Pool Home Close to Disney & Universal
    Price: €69/night €669/week €1,382/month
  • Bedrooms: 4, sleeps 10
  • Bathrooms: 3
    • Contact Owner
Tropical Lakefront Villa! Only 5 mins to Disney!, Kissimmee
Tropical Lakefront Villa! Only 5 mins to Disney!
    Price: €73 - €114/night
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 3
    • Contact Owner

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There are no vacation rentals within Maitland, Florida. We broadened your search to include all rentals within 25 miles.

Four BR Disney 3mi Secluded Pool 52 in HDTV PS2, Kissimmee
Four BR Disney 3mi Secluded Pool 52 in HDTV PS2
Contact Owner
Nightly rate from
€82
5 of 5 stars 20 reviews
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 3
Min stay:3
Stay at our very popular villa for 5 Star Luxury in the Sun! This large single story 4 bedroom, 3 bath Florida vacation home in Lindfields Estates is right ...
  • Nightly
    €82 - €97
  • Weekly
    €567 - €676
  • Monthly
    --
Kissimmee Dog Vacation Home Indian Ridge Oaks, Orlando
Kissimmee Dog Vacation Home Indian Ridge Oaks
Contact Owner
Nightly rate from
€104
5 of 5 stars 15 reviews
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
Rent an affordable pet friendly kisimmee vacation home rental in the community of Indian Ridge Oaks in Orlando, Florida. You can now bring your family pets ...
  • Nightly
    €104
  • Weekly
    --
  • Monthly
    €2,425
Best Disney Value !!! Private Pool Vacation Home, Kissimmee
Best Disney Value !!! Private Pool Vacation Home
Contact Owner
Nightly rate from
€118
4 of 5 stars 2 reviews
Management: Verified owner
Property: Rental Home
Bedrooms: 5, sleeps 12
Bathrooms: 4
Min stay:5
Dont just Settle for a Vacation Home. Rent a Luxury Vacation Home in a Vacation Resort ! THE BEST OF BOTH WORLDS...You have your very own professionally ...
  • Nightly
    €118 - €173
  • Weekly
    €824 - €1,212
  • Monthly
    €2,079
Windsor Hills Orlando Lakefront Villa, Orlando
Windsor Hills Orlando Lakefront Villa
Contact Owner
Nightly rate from
€132
5 of 5 stars 21 reviews
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 5
Rent Direct From Owner! David & Fran's Orlando Lakefront Villa. Our 'closest to Disney' 5-bed 5-bath vacation home with private pool & spa is on the lakefront ...
  • Nightly
    €132 - €194
  • Weekly
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  • Monthly
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AAA*****SIMBAS' PRIDE @ Emerald Island Resort, Kissimmee
AAA*****SIMBAS' PRIDE @ Emerald Island Resort
Contact Owner
4 of 5 stars 1 review
Management: Verified owner
Property: Rental Home
Bedrooms: 6, sleeps 13
Bathrooms: 5
Min stay:7
Family Friendly Home on Disneys Doorstep in the 192 Corridor!! So Close you can see the fireworks!! SIMBA'S PRIDE (Sleeps 12 plus infant)Where the magic ...
  • Nightly
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  • Weekly
    €1,195 - €1,628
  • Monthly
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Orlando Pet Vacation Home Hotel Indian Ridge Oaks, Kissimmee
Orlando Pet Vacation Home Hotel Indian Ridge Oaks
Contact Owner
Nightly rate from
€104
5 of 5 stars 19 reviews
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 2
Rent a pet friendly orlando vacation rental near Universal Studios or Disney World in the community of Indian Ridge Oaks in Kissimmee, Florida. You can now ...
  • Nightly
    €104
  • Weekly
    --
  • Monthly
    €2,425
Windsor Hills 6BR, 4BA across from children's park, Kissimmee
Windsor Hills 6BR, 4BA across from children's park
Contact Owner
Nightly rate from
€139
4 of 5 stars 3 reviews
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 6, sleeps 12
Bathrooms: 4
Min stay:1
Welcome to our six bedroom, four bathroom, non-smoking, private vacation home in Windsor Hills Resort. You cannot find a closer resort community to Walt ...
  • Nightly
    €139 - €163
  • Weekly
    --
  • Monthly
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Windsor Palms Conservation View 5 Bed Home, Kissimmee
Windsor Palms Conservation View 5 Bed Home
Contact Owner
Nightly rate from
€139
4 of 5 stars 2 reviews
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 4
So close to Disney World you can almost touch it - Windsor Palms is the premier resort for the guest looking for all the excitement that the theme parks ...
  • Nightly
    €139
  • Weekly
    --
  • Monthly
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Sunshine Florida Villa, Kissimmee
Sunshine Florida Villa
Contact Owner
4.5 of 5 stars 3 reviews
Management: Verified owner
Property: Rental Home
Bedrooms: 6, sleeps 14
Bathrooms: 5
Location Terra Verde, Kissimmee, Florida, (10 minutes from Disney) Accommodation: Villa - 6 Bedrooms plus separate children’s TV-Games console ...
  • Nightly
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  • Weekly
    €963 - €1,247
  • Monthly
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Spectacular 8 Bedroom 'Grand Formosa' 9,300 Sq Ft, Kissimmee
Spectacular 8 Bedroom 'Grand Formosa' 9,300 Sq Ft
Contact Owner
4 of 5 stars 2 reviews
Management: Verified owner
Property: Rental Home
Bedrooms: 8, sleeps 16
Bathrooms: 9
This spectacular Villa is located at ‘The Estates Formosa Gardens’ Kissimmee, the closest community to Disney World. Formosa is renowned for its prestigious ...
  • Nightly
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  • Weekly
    €3,430 - €4,504
  • Monthly
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DisneyDreamVilla, Kissimmee
DisneyDreamVilla
Contact Owner
Nightly rate from
€123
4.5 of 5 stars 2 reviews
Management: Verified Plus owner
Property: Villa
Bedrooms: 5, sleeps 12
Bathrooms: 5
Closest to Disneyworld! DisneyDreamVilla is a luxury 5 bedroom / 5 bath private villa with screened pool and hot spa on an extended lanai. The villa ...
  • Nightly
    €123 - €191
  • Weekly
    €858 - €1,334
  • Monthly
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WDW villa in 5 star Windsor HIlls Resort, Kissimmee
WDW villa in 5 star Windsor HIlls Resort
Contact Owner
Nightly rate from
€69
4 of 5 stars 1 review
Management: Verified owner
Property: Villa
Bedrooms: 3, sleeps 6
Bathrooms: 3
Our beautifully furnished 3 bedroom townhome is located in the prestigious five-star gated resort community of Windsor Hills, just one mile (2 traffic ...
  • Nightly
    €69 - €82
  • Weekly
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  • Monthly
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"The Water's Edge" The classiest of them all, Kissimmee
Contact Owner
Nightly rate from
€274
4 of 5 stars 3 reviews
Management: Verified owner
Property: Rental Home
Bedrooms: 7, sleeps 19
Bathrooms: 6
Formosa Gardens Florida Vacation Rental Home. 7 Bedroom 6 Bathroom South facing pool, lake view sleeps 16-19 WOW!!! Even the other villa owners say this ...
  • Nightly
    €274 - €312
  • Weekly
    €1,923 - €2,144
  • Monthly
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Disney World pvt pool game, Princess & Mickey room, Kissimmee
Disney World pvt pool game, Princess & Mickey room
Contact Owner
4 of 5 stars 3 reviews
Management: Verified owner
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
Gorgeous home with all the bells & whistles! Home's view from private pool looks over the Prestigious Mystic Dunes Golf Course. View from extra large pool ...
  • Nightly
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  • Weekly
    €485 - €554
  • Monthly
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"Scotch Corner" 4 Bedrooms & South Facing Pool, Kissimmee
Contact Owner
Nightly rate from
€76
4.5 of 5 stars 4 reviews
Management: Verified owner
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
"The home has been luxury furnished throughout all personally chosen with comfort in mind giving you a home from home feeling. We are only 6 Miles from Disney ...
  • Nightly
    €76 - €103
  • Weekly
    €506 - €721
  • Monthly
    --
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns