
House holiday rentals in Maitland
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Top-rated house rentals in Maitland
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Popular amenities for house rentals in Maitland
House rentals with a pool

Quiet Place, convenient to everything!
The home is as described. Nice and Clean. Quiet neighborhood. Highly Recommend!!!!

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool
Very nice inside and spacious backyards closed in games for the children and family to do lots of beds I like that you can shut the master door and everybody can still get to the bathroom as a huge thing for me.

Modern Tropical House Heated Salt Pool
I had a wonderful stay at this property. The host provided clear and concise instructions, making the check-in process seamless. The house itself is beautiful, offering a perfect balance of privacy and comfort. Renting the entire place gave us the space we needed, and it came equipped with all the essentials. Highly recommend for anyone looking for a relaxing and practical getaway!

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
We where in Orlando to go to my granddaughters graduation & this home just made it a perfect vacation - so comfortable - & clean & the pool & outside area was amazing !!

Year around Heated Pool 7 min from Airport!
Super nice, pictures do not do it justice. Upgrades clearly done little by little. Pool is amazing, outdoor area great, cozy yet spacious. Would book here again and again. 20 min from Camping World Stadium, 15 min from Downtown Orlando truly accurate, easy in and out from main road and highways.

Private Pool at Flamingo Cottage
Our family stayed at Marilyn’s home for a few days to relax and enjoy her pool during our kiddo’s graduation week. She was very accommodating, had clear requests and instructions, and was quick to respond to my own messages. There were zero issues with communication or amenities. Thanks for an easy trip, Marilyn!

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney
Wonderful hosts, had a great experience. I would definitely revisit if the opportunity comes again.

Tropical Oasis - Heated Luxury Pool - Game Room
Booked the house for the heated pool, backyard, open kitchen and bright dining area overlooking the backyard... we were not disappointed. The pictures definitely represent the house. The heated pool was adjusted to just the right temp; the backyard was open, spacious and private; the kitchen had updated appliances with an open floor plan and plenty of countertop space; and the bright dining area off the kitchen overlooking the backyard had large clean windows. While the house was larger than our needs in terms of occupancy, the things we wanted and enjoyed were worth the upgrade. Laura was also very responsive to any questions we asked or concerns we had.
Weekly house rentals

Cozy Blue Bungalow
This is our second time there We enjoyed staying there . Paul is just a phone call away and very quick respond . When we look to stay in the area the blue bungalow is the place to stay

Clean, cozy home in a GREAT location
So this was my SECOND stay with Danie in 2 months. This place DOES NOT DISAPPOINT!!! This is such a well-appointed home with everything you need to feel at home! The neighborhood is quiet and feels very safe, the back yard is an oasis of peace, and cooking a meal to eat in the breakfast nook or at the gorgeous family-sized trestle table is a joy! There is plenty of space for everyone to feel comfortable...I was there with my friend and our two teenagers. We cooked together and enjoyed movies on the nice big TV in the living room, where everyone had plenty of room to stretch out. Plenty of hot water (we all had to shower after going to the parks in Orlando) and soft towels. We slept like babies and awoke refreshed and ready for the next day. We enjoyed watching the squirrels and birds from the screened porch while sipping our coffee. Danie's place is home away from home! Thanks so much for this wonderful escape that feels so friendly and familiar every time I come back!

Cozy home 5min to Park Ave and Downtown Orlando
The location of the Airbnb was perfect for me! It was walkable to the venue I needed to go to, and it was so close to everything Winter Park has to offer. The decoration inside the house was well suited for the space, and I really loved my experience here. I would definitely book this again next time I’m in the area.

Lakefront Paradise Near Attractions
What a lovely home this is. Very thoughtfully done and beautiful setting. Our contact person Gabriel was very very responsive. There were three couples staying here together and there was plenty of room to enjoy visiting or alone time.

The Winter Park Experience
The host was incredible and attentive to every detail. From start to finish the experience was seamless. The host was responsive and accommodating and made sure we felt like home when we were staying there. The host went above and beyond for us. There are not enough good words for me to say about the host, we highly recommend staying here. 12/10 experience

Orlando Poolside Oasis
My friends and I really enjoyed the house it was very clean, well-organized, and overall a great place to stay. We didn’t encounter any issues, except for the lack of lighting in the backyard at night, which made it difficult to use the pool after dark. It wasn’t a major problem, but having some outdoor lights would definitely be a nice addition. Other than that, everything was perfect! The owners were very helpful and even allowed us early check-in, which we truly appreciated.

May Discounts! Close to Disney & Universal Parks!
Everything was perfectly fine, only upon entry the floors definitely were not swept well or mopped. As far as just that the stay was great. Video games were a treat for us, got to jam out on guitar hero and enjoy my time there. Definitely recommend the stay !

Lakefront House ~ Pool ~ 5 Star Location
WOW! What a great place. Very picturesque. Enjoyed the lakefront, pool, private. Location is close to the Altamonte Mall and alot of retail, restaurants, etc - however, the location is tucked away and you would never know it.
Private house rentals

Winter Park Guest Suite near UCF/FullSail/Rollins!
We came from South Carolina to visit our son who is a musician that recently graduated from Full Sail. Valerie's place is in the same neighborhood where he stays. The studio was just as pictured and described - cute, cozy, and quiet! It makes me want to convert our garage into an in-law sweet because of how perfectly everything was done!

NEW! ☀Bungalow+Patio+FirePit! Close to Everything!
Overall our stay was great! The only snag was the place hadn’t been cleaned when we arrived due to a booking/communication error. Greg immediately responded and had cleaners there within the hour. Once It was cleaned the place was immaculate and our stay was peaceful - exactly what we were looking for!

3 BR minutes walk to Park Avenue
Solid place with great proximity to restaurants.

Charming Bungalow in Winter Park
Loved the stay at this place! The instructions were clear on how to get to the parking and the large kitchen island was a great gathering spot. This house had more than enough space for what our needs were. Host was very responsive. Thank you for having us!

Sunset Lake Retreat
Comfy beds - I swear that’s a rare find nowadays! If you like a soft, cozy bed - this master bedroom has you covered! The house is somehow even more beautiful than the photos. It was easy to find, door code made it easy to access and even though we just stayed one night, we felt right at home. Highly recommend this home!

Lake Front Home near Winter Park!
There were four of us. we absolutely loved our stay. the house was very clean and comfortable. we loved the awesome kitchen and how roomy the whole place was. the outside porch was especially nice. waking up each morning and having our coffee out on the porch was super. there were plenty of towels and blankets. we were not far from restaurants and grocery stores. when we had a question for Richard he responded in a very timely manner. we would highly recommend this house as a clean and safe place to stay.

Blue Villa | 8 PPL | Heated Pool | BBQ | Top Area
The palace looked exactly like your pictures! The pool was perfect! Great communication

Beautiful 2 Bed/1 Bath College Park Home
We had a wonderful stay at Alec’s place! He was very communicative and provided clear, easy-to-follow instructions. Check-in was smooth and flexible. Really appreciated being able to check in early after a long red-eye flight. The space was clean, comfortable, and located in a quiet residential neighborhood. Would definitely recommend staying here!
Quick stats about house rentals in Maitland
Total rentals
60 properties
Total number of reviews
1.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- Playalinda Beach
- ESPN Wide World of Sports
- Titusville Beach
- Amway Center
- Epcot
- Daytona International Speedway
- Magic Kingdom Park
- Reunion West
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- Blue Spring State Park