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Places to stay in Maitland

Book unique places to stay, houses, and more on Airbnb

Top-rated places to stay in Maitland

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Home in Kissimmee

4.82 out of 5 average rating, 34 reviews

The Nest

AndrewRating, 5 stars1 week ago

The space really speaks for itself. Comfortable, clean, and spacious. We frequented Disney parks, Disney springs, Volcano bay, and a few of our favorite local spots like Congo River Golf and this bnb made it easy to get to all these places. Juan is a great host, very responsive and friendly. We would definitely stay again!

Home in Davenport

4.67 out of 5 average rating, 6 reviews

Queen Beds | Private Pool | Super Fast WIFI

ChristopherRating, 5 stars4 months ago

Dillan invited myself and my friends into his home and helped us make the most of our trip. Everything is exactly what it is described as and more. The home is beautiful and Dillan is ready to help should anything happen. We locked ourselves out one of the rooms and Dillan provided us with a solution within twenty mins of me reaching out to him. We got into a car accident and he was more than happy to help us in working out a check out time that allowed us time to get a rental. The next time I plan on going to Davenport I will be staying in at Dillan’s home.

Villa in Kissimmee

4.99 out of 5 average rating, 214 reviews

Disney-Themed Home w/ Game Room & Private Hot Tub!

MarieRating, 5 stars2 weeks ago

Our Family had such a fun time at Kevins place that my daughter refused to go home at checkout and asked if we could stay longer . The house is beautifully decorated with lots of kid favorites like Elsa and Mickey ; our favorite was the Harry potter game room so nice. We were all very comfortable and had everything we could think of pool towels, crib, high chair, kid dinnerware floaties, life jackets…The house is less than half an hour from Universal and Disney. Kevin was a great host very responsive and proactive and did I mention NO CHORES at checkout 🙂 that was so refreshing because I got used to having host request to take the trash out, load the dishwasher, put the used sheets in the washing machine and so on. Thank you for being AWESOME Kevin, we will be back soon 😊

Home in Orlando

4.83 out of 5 average rating, 24 reviews

Lakeview, Pool, 4 beds! 13 min to DT

MercyRating, 5 stars4 weeks ago

This was a great stay mainly due to the pool, that was not heated so too cool to use but nice, but also a good sized lake on the other side of the pool. Sitting outside, reading, birding, writing, knitting, was heaven. We came from the cold tail of winter in New Hampshire so it was nice not to be wearing layers and down. The jets going overhead were only a tad bothersome. (It’s true what they say about getting used to chronic noise, lol). And it would have been nice to be able to keep the slider open for the fresh air and breezes, but no. There is a pool alarm on the slider that’s pitched loudly after 15 seconds so it must stay closed. I messaged Michelle with a few suggestions that if fixed will make this a total five star. Waste baskets in the bathrooms. More silverware. A couple more blankets. She wrote that she would take care of it. And, yes, we would rent this again…for the location on the lake. Thank you, Michelle. Mercy V-

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Maitland places to stay

Laptop-friendly workspace

Stay near Maitland's top sights

Enzian Theater77 locals recommend

Winter Park Village68 locals recommend

Regal Cinemas Winter Park Village43 locals recommend

Starbucks39 locals recommend

Whole Foods Market34 locals recommend

Publix Super Market at Winter Park Village25 locals recommend

Other great vacation rentals in Maitland

Home in Davenport

4.76 out of 5 average rating, 67 reviews

Vacation home

JaniquaRating, 5 stars1 week ago

Me and my Family enjoyed our days there! Miguel was very friendly and nice and welcome us to a little welcome gift I mean who dosen’t love chocolate

Home in Davenport

5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

IrynaRating, 5 stars15 months ago

Nice house with good layout of rooms. It is very convenient to come with children as there is a lot of entertainment on the territory of the complex. I also liked the themed design of the rooms. Overall, this is a good house for a large and friendly company.

Townhouse in Kissimmee

4.94 out of 5 average rating, 187 reviews

Beautiful family home near all attractions.

NicholasRating, 5 stars1 week ago

Thank you Peter and Carolina for allowing my family to stay in your house! The house was immaculate when it came to cleanliness. Peter was very attentive to my messages and responded quickly. This was by far the best house that I've stood at within the Encantada community. Highly suggest staying here. We will definitely be coming back!

Home in Kissimmee

5 out of 5 average rating, 7 reviews

Lovely home away from home!

ChristaRating, 5 stars3 months ago

Great place. Very kid friendly and the layout was perfect. Not too far from Disney properties also. It worked out very well for our group. Resort was nice too. Property managers were very responsive. Overall I would recommend.

Home in Four Corners

4.86 out of 5 average rating, 14 reviews

DisneyVacationHomeLazyRiver9021

CraigRating, 5 stars3 weeks ago

Great house and host, easy check-in and check-out. Quickly and easily resolved our small check-in issue, will definitely recommend and stay again when in the area.

Townhouse in Kissimmee

4.83 out of 5 average rating, 69 reviews

Entire Townhouse -Kissimmee, 4 Bedrooms 3 Bath

VanessaRating, 5 stars2 months ago

Carmen is an excellent host! The house is lovely, very well-equipped, the condominium is complete. Plus, it's very close to Disneyland. We loved it, we'll definitely be back!

Condo in Kissimmee

4.68 out of 5 average rating, 66 reviews

Disney, Villa Runaway Beach, Kissimmee 2

BrendaRating, 5 stars2 weeks ago

Monica and Sebastian have a beautiful place, home feeling and absolutely beautiful. Getting into the place was easy and getting in the home was very easy too. We were very happy with our stay. The apparent is cozy and the apartment complex is very beautiful and super clean. We enjoyed our stay. Thank you Brenda and Manny

Home in Davenport

4.63 out of 5 average rating, 8 reviews

Stylish Resort Townhome by Disney w/ Perks Galore

BriannaRating, 5 stars2 weeks ago

Our stay was absolutely amazing! The home is exactly as pictured and was extremely clean. We’re walking distant from the waterpark on the resort which was perfect. My only recommendation is to be prepared for an insane and chaotic wait 30mins+ at the gate to get into the resort during the evenings. This has NOTHING to do with the host and everything to do with resort setup itself. We plan to come back this summer & hopefully it’ll be a smoother process. Thanks Manuel for a great stay!

Quick stats about vacation rentals in Maitland

Total rentals
70 properties
Total number of reviews
2.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

How much does it cost to stay in apartment rentals in Maitland?
Experience the best of Maitland with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Maitland?
Yes! Work meets play with ease at over 30 vacation rentals in Maitland featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for Apartment Rentals in Maitland?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a gym, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Maitland?
Four-legged friends are welcome in Maitland. Choose from more than 30 vacation rentals for guests traveling with pets.
Do house rentals in Maitland have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Maitland. Enjoy a tailored experience with all the comforts you desire.
Are there Maitland apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 apartment rentals with pools in Maitland, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Maitland have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Maitland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maitland have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Maitland. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Maitland have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Maitland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Maitland?
Maitland has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore