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House vacation rentals in Maitland

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Popular amenities for Maitland house rentals

House rentals with a pool

Guest favorite
Home in Orlando
4.88 out of 5 average rating, 123 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

SuzanneRating, 5 starstoday
Had a nice stay with family and friends at Alyssa’s place along with 2 dogs. Was so nice to be able to bring out pets along on vacation. The house was clean, beds were comfortable, lots of space. I Spent most of my time out in the pool which was amazing.
Top guest favorite
Home in Sanford
4.99 out of 5 average rating, 143 reviews

The Cypress House

IvetteRating, 5 stars1 week ago
I had such a great stay here! From the moment I arrived, everything felt warm and welcoming. The house was spotless and exactly like the photos no surprises, just comfort. Kim was fantastic super responsive, which made the whole experience even better. One of my favorite parts was the peaceful backyard. It was the perfect place to unwind. I truly felt at home and would absolutely stay again. Thank you for such a lovely experience
Superhost
Home in Altamonte Springs
4.82 out of 5 average rating, 129 reviews

Quiet Place, convenient to everything!

FrancisRating, 5 stars1 month ago
The home is as described. Nice and Clean. Quiet neighborhood. Highly Recommend!!!!
Guest favorite
Home in Orlando
4.9 out of 5 average rating, 146 reviews

Modern Tropical House Heated Salt Pool

LuisRating, 5 stars3 months ago
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!
Guest favorite
Home in Sanford
4.87 out of 5 average rating, 245 reviews

Private Pool at Flamingo Cottage

KristenRating, 5 stars2 weeks ago
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!
Superhost
Home in Orlando
4.87 out of 5 average rating, 194 reviews

Year around Heated Pool 7 min from Airport!

JoseRating, 5 stars3 days ago
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.
Top guest favorite
Home in Clarcona
4.96 out of 5 average rating, 110 reviews

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney

BillRating, 5 stars1 week ago
Wonderful hosts, had a great experience. I would definitely revisit if the opportunity comes again.
Guest favorite
Home in Longwood
4.89 out of 5 average rating, 104 reviews

Tropical Oasis - Heated Luxury Pool - Game Room

AnneRating, 5 stars1 month ago
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

Guest favorite
Home in Altamonte Springs
4.93 out of 5 average rating, 43 reviews

Secluded Pool Getaway

MariaRating, 5 stars3 weeks ago
We all enjoyed our stay. The house was very well maintained, clean & we appreciated the extra supplies in the house. The host was very responsive, helpful & friendly! The location was great, just minutes from I4. Would recommend to everyone!
Superhost
Home in Winter Park
4.85 out of 5 average rating, 96 reviews

Funky Remodeled Otown Bungalow Sleeps 8

DylanRating, 5 stars2 weeks ago
Place was very nice super modern and very cozy thanks!
Guest favorite
Home in Maitland
4.91 out of 5 average rating, 80 reviews

Lake Front Home near Winter Park!

NancyRating, 5 stars1 month ago
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.
Guest favorite
Home in Casselberry
4.92 out of 5 average rating, 25 reviews

Blue Villa | 8 PPL | Heated Pool | BBQ | Top Area

DebbieRating, 5 stars3 days ago
The palace looked exactly like your pictures! The pool was perfect! Great communication
Guest favorite
Home in Winter Park
4.92 out of 5 average rating, 53 reviews

Lakefront Paradise Near Attractions

CathyRating, 5 stars1 month ago
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.
Top guest favorite
Home in Winter Park
5 out of 5 average rating, 39 reviews

The Winter Park Experience

EmilyRating, 5 stars1 month ago
We couldn’t ask for a more perfect place to stay for a long weekend in Orlando with our extended family. The house is so welcoming and all the beds were clean and comfortable. We will absolutely be back because we visit family in Orlando a lot. This is a great place to stay.
Top guest favorite
Home in Orlando
5 out of 5 average rating, 21 reviews

King/Queen Quiet Vibey Bungalow

LydiaRating, 5 stars3 days ago
The home was clean and comfortable. Plenty of Restaurants nearby, in walking distance. Chris was very responsive and friendly. I would definitely stay here again.
Top guest favorite
Home in College Park
5 out of 5 average rating, 12 reviews

3BR Oasis DT ORL, Full Kitchen & Fenced Yard!

DomineRating, 5 stars3 days ago
Such a lovely and cute place! We will definitely be back if we are in Orlando again! The space was perfect for us and a calming retreat to come home to.❤️

Private house rentals

Guest favorite
Home in Orlando
4.92 out of 5 average rating, 62 reviews

Villa Pilar | KingBed • Outdoor Kitchen & Dining

HeatherRating, 5 stars2 weeks ago
First of all, the host is WONDERFUL. She was very responsive and even followed up after the first night to make sure everything was okay. There was ample space for our whole family.
Superhost
Home in Altamonte Springs
4.88 out of 5 average rating, 32 reviews

Cozy Blue Bungalow

EdwinRating, 5 stars1 week ago
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
Top guest favorite
Home in Baldwin Park
5 out of 5 average rating, 53 reviews

SEEN ON TV! Private Resort, Nintendo-theme Game Rm

RichardRating, 5 stars2 weeks ago
Caitlin was incredibly responsive whenever we had a question about anything. The house was incredible, they took so much time and money making all the amenities and details first class. Everything was explained in easy to read pamphlets that described everything. The game room was a big hit, and of course the bbq and pool area, and my family absolutely loved it. Everyone was raving at how nice a place the house was. I highly recommend staying here if you can, I would definitely rent again if we’re ever back in the area.
Guest favorite
Home in Winter Park
4.85 out of 5 average rating, 54 reviews

NEW! ☀Bungalow+Patio+FirePit! Close to Everything!

DebbieRating, 5 stars2 weeks ago
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!
Guest favorite
Home in Altamonte Springs
4.84 out of 5 average rating, 55 reviews

Near Orlando Attractions Wekiwa Springs House

BradRating, 5 stars3 weeks ago
Great value. The cozy home is on a dead end street which makes it a quiet place with little noise / traffic. We wanted to be near Sanlando Park, so location was ideal for us. It is also nice for getting to New Smyrna Beach, less than an hour away. I also really liked the furniture which includes several nice, quality wooden pieces. I would 100% stay here again.
Guest favorite
Home in Orlando
4.98 out of 5 average rating, 45 reviews

Charming Bungalow in Winter Park

TaralynnRating, 5 stars4 days ago
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!
Guest favorite
Home in Orlando
4.93 out of 5 average rating, 91 reviews

Luxurious and modern cottage near UCF

CassieRating, 5 stars2 weeks ago
Drove down for formula drift & it was the perfect spot in a quiet neighborhood! Very clean & tidy & the decor made you feel right at home. Definitely recommend staying here if you’re in the area!
Guest favorite
Home in Winter Park
4.95 out of 5 average rating, 20 reviews

New built Private Studio Orlando/Winter Park area

GregoryRating, 5 stars3 weeks ago
This sweet little suite met all my needs for a week visiting friends. There was an internet problem one day, but Diana stayed in communication with me and the malfunction was corrected in a timely manner. The place is clean and well-appointed. I highly recommend it, and I would definitely return.

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

Destinations to explore

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  5. Maitland
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