Are there vacation rentals with a dedicated workspace in Maitland?

Yes! Work meets play with ease at over 40 vacation rentals in Maitland featuring dedicated workspaces. Stay connected and productive in your home away from home.

Do apartment rentals in Maitland have air conditioning?

Absolutely! We offer over 20 apartment rentals with air conditioning in Maitland. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Maitland have a kitchen?

Absolutely! We offer over 30 house rentals with a kitchen in Maitland. Enjoy a tailored experience with all the comforts you desire.

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 free parking, over 10 homes with a kitchen, over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Are there family-friendly vacation rentals in Maitland?

Maitland has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

How much does it cost to stay in apartment rentals in Maitland?

Experience the best of Maitland with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Are there Maitland vacation rentals on Airbnb with pools?

Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Maitland, available on Airbnb. Make a splash and soak up the sun in style!

Are there pet-friendly vacation rentals in Maitland?

Four-legged friends are welcome in Maitland. Choose from more than 20 vacation rentals for guests traveling with pets.

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 free parking?

Absolutely! We offer over 40 house rentals with free parking in Maitland. Enjoy a tailored experience with all the comforts you desire.

Maitland vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Maitland

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Villa in Kissimmee

4.89 out of 5 average rating, 56 reviews

SuperHost! Entire New Home! Pool, Near Dis! LOW $!

As Airbnb Superhosts for 7 consecutive years, we'll give you the most perfect home and experience! Believe your eyes! We just gave this beautiful home a total makeover, brand new decor, etc. Gorgeous from top to bottom! Granite kitchen with new cabinets, spectacular dining room -- this home has everything you could ever ask for plus 3 BR's/2 Baths, and slps 7. Your private patio/balcony overlooks a nature preserve. Heated pool, BBQ area, spa, tennis, fitness center, and just 7 min's from Dis!

Guest favorite

Home in Kissimmee

4.94 out of 5 average rating, 16 reviews

My Disney Villa

Looking for the ultimate vacation spot near Disney Orlando and Epcot? Look no further! Our newly renovated large 5-bedroom Airbnb is just a genuine 12-minute drive away from these amazing parks, Our home features 2 amazing themed rooms, including a state-of-the-art Star Wars and Mickey Mouse rooms that will surely make your kids feel like they're in their own magical world. We also have 3 large adult rooms, each equipped with comfortable beds, a huge pool area with new furniture, 2 dining areas

Superhost

Tiny home in Kissimmee

5 out of 5 average rating, 9 reviews

2766 Disney Universal Sea World 1 Bedroom

Located at "MILL CREEK SUN RESORT" voted best Disney area resort by "Tewks & Tani" Just a short drive to the entrance to "Walt Disney World" and around the corner from "THE LOOP" shopping area Great place in clean, safe resort Outside deck with table and chairs Private driveway Kitchen with utensils, dinnerware, cookware ect. Queen bed in separate bedroom Pullout couch in the living room Dining area with table and chairs Towels and linens included Modern Gym Swimming Pool Playground Dog Park

Superhost

Home in Kissimmee

4.9 out of 5 average rating, 52 reviews

Free Pool Heat! Baby Safe w *Indoor PlayGround*

*Free POOL HEAT*Close to Disney Parks! Home equipped for baby! Full nursery, double stroller, highchair, packnplay, outlet covers, baby gates, toys, books, bouncy, and more. Kids love the Toy Story indoor playground with ball-pit, trampoline & slide, the fun doesn't stop at Disney! 6 themed bedrooms (3 Kids & 3 Adult themes), 5 baths, appliance stocked kitchen, a movie/game loft w/ 2 queen sofa sleepers, in-ground pool and Jacuzzi with BABY GATE! Fully furnished high-end patio and pool area.

Guest favorite

Home in Kissimmee

5 out of 5 average rating, 16 reviews

Disney Vacations Oasis

Experience the best of Disney's area with the comfort and luxury of our home. Whether you're here for adventure or relaxation, we provide everything you need for an unforgettable stay. We prioritize your health and safety. Our home undergoes a thorough professional cleaning and sanitization process prior to your arrival, ensuring every surface is spotless and ready for you to enjoy. Great amenities, including lazy river, restaurant, bar, gym and everything you may need during your stay.

Guest favorite

Villa in Kissimmee

4.8 out of 5 average rating, 60 reviews

Home w/ PVT Pool, Game Room & Resort access 2100

Our luxurious 5-bedroom, 5.5-bathroom home boasts a spacious living room with Smart TV, a fully-equipped kitchen and dining room, a cozy upstairs living area perfect for movie nights as well as an air-conditioned game room featuring a pool table and air hockey. Venture to the backyard to find even more amazing features such as a spacious private pool and SPA, sun loungers, a barbecue and a table with 6 seats where you and your guests will be able to enjoy some sun-filled al fresco dining.

Guest favorite

Home in Osceola County

4.8 out of 5 average rating, 5 reviews

Amazing vacation spot near Disney! - 7105

Imagine this cozy getaway in a lush gated community, just a stone's throw away from the magic of Disney. This vacation home boasts four thematic bedrooms, perfect for hosting your family and friends. Step into the clubhouse, with an amazing bakery. It's the ideal spot for unwinding after a day of adventure in the nearby theme parks. With its welcoming atmosphere and convenient location, this retreat offers the perfect blend of relaxation and excitement for your dream vacation. Book now!

Superhost

Townhouse in Davenport

4.83 out of 5 average rating, 36 reviews

Vacation Townhome Davenport ChampionsGate

This rental is gorgeous Townhome located in Davenport Champion Gate, and it sits in the perfect spot for family vacation, meeting friends, or a couple’s getaway. You will be close to everything when you stay at this centrally-located place. You have plenty of choices from Disney parks, Water parks, Universal Studios, Canoeing, Obstacles Park, Paddleboard to Shopping, and Nights on the Oldtown. There’s something for everyone in your group. Recreation area with FREE mini golf, and pool

Guest favorite

Condo in Kissimmee

4.95 out of 5 average rating, 153 reviews

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Guest favorite

Apartment in Kissimmee

4.86 out of 5 average rating, 218 reviews

Modern Great Villa near Disney & Parks

This place is 5 up to 20 minutes to all of orlando's amusement and water parks!. One of the best units in this resort, just book and see for yourself. An excellent unit with great reviews. There is an awsome pool and jacuzzi onsite (Please note, sometimes the jacuzzi breaks down and may not work during your stay). high speed wifi. easy smooth self checkin with a private keypad code that is being replaced between each new guest, walking distance to many shops and plazas, free parking.

Superhost

Home in Davenport

4.85 out of 5 average rating, 20 reviews

Charming Vacation Cottage

Enjoy your own cottage in a resort atmosphere with lots of amenities and activities. Fully furnished, all bedding, kitchen needs and washer and dryer. Easy access to Disney Resorts, Lego Land, Bok Tower Gardens, Sea World, Universal, Disney Springs and other Central Florida attractions. On-site heated pool, miniature golf, pickle ball, shuffle board, horseshoes, fitness center, library and billiards. Some pet friendly units. Book your next vacation with us.

Superhost

Apartment in Davenport

5 out of 5 average rating, 3 reviews

Bahama Bay Resort * Disney Area

Bahama Bay is a Gated Resort just 10 miles from Disney! With 4 Pools * 6 Hot Tubs * A Splash Pad * Shuffleboard * Sandy Beach Area * Tiki Bar Restaurant * Walking Trails & More is a great place for a Vacation! * NO Resort FEE * Parking is FREE! Resort Villa * 2nd floor Villa * 4 Swimming Pools * 6 Hot tubs * White sandy Beach * On-site Restaurant Tiki & Bar * Beach Volleyball * Tennis * Pickle Ball * Basketball * Fishing * Nature Trails *

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Maitland vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Maitland's top sights

Charles Hosmer Morse Museum of American Art168 locals recommend

Enzian Theater77 locals recommend

Winter Park Village68 locals recommend

Regal Cinemas Winter Park Village43 locals recommend

Starbucks39 locals recommend

Whole Foods Market34 locals recommend

Other great vacation rentals in Maitland

Guest favorite

Townhouse in Kissimmee

4.94 out of 5 average rating, 113 reviews

Meriggiare! Perfect for Disney Vacation! FREE WiFi

Superhost

Home in Davenport

5 out of 5 average rating, 4 reviews

New! Windsor Island Resort with pool by Disney 03

Guest favorite

Townhouse in Kissimmee

4.93 out of 5 average rating, 183 reviews

Beautiful family home near all attractions.

Superhost

Home in Kissimmee

4.81 out of 5 average rating, 21 reviews

Vacation Home with Pool & Spa near Disney

Guest favorite

Home in Kissimmee

4.81 out of 5 average rating, 32 reviews

2611-VP Beautiful 4 Bd Home, Lake View & Pool

Guest favorite

Home in Orlando

4.93 out of 5 average rating, 27 reviews

Relaxing four bedroom getaway built 4 long stays

Guest favorite

Home in Kissimmee

4.77 out of 5 average rating, 111 reviews

Lovely T/H near Disney & Universal, Fits 8 people

Guest favorite

Home in Maitland

4.98 out of 5 average rating, 56 reviews

Florida Poolside Paradise a Great Place to Unwind!

Show all

Quick stats about vacation rentals in Maitland

Total rentals
80 properties
Total number of reviews
2.3K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Maitland?
Yes! Work meets play with ease at over 40 vacation rentals in Maitland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Maitland have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Maitland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maitland have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Maitland. Enjoy a tailored experience with all the comforts you desire.
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 free parking, over 10 homes with a kitchen, over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Maitland?
Maitland has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Maitland?
Experience the best of Maitland with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Maitland vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Maitland, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Maitland?
Four-legged friends are welcome in Maitland. Choose from more than 20 vacation rentals for guests traveling with pets.
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 free parking?
Absolutely! We offer over 40 house rentals with free parking in Maitland. Enjoy a tailored experience with all the comforts you desire.

Maitland vacation rentals

Top-rated vacation rentals in Maitland

Villa in Kissimmee

Home in Kissimmee

Tiny home in Kissimmee

Home in Kissimmee

Home in Kissimmee

Villa in Kissimmee

Home in Osceola County

Townhouse in Davenport

Condo in Kissimmee

Apartment in Kissimmee

Home in Davenport

Apartment in Davenport

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Maitland vacation rentals

Stay near Maitland's top sights

Other great vacation rentals in Maitland

Townhouse in Kissimmee

Home in Davenport

Townhouse in Kissimmee

Home in Kissimmee

Home in Kissimmee

Home in Orlando

Home in Kissimmee

Home in Maitland

Quick stats about vacation rentals in Maitland

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore