Vacation rentals in Maitland

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Top-rated vacation rentals in Maitland

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Guest favorite

Apartment in Winter Park

4.95 out of 5 average rating, 283 reviews

Get a Little Glam in a Retro Palm Beach-Style Boudoir

The whole upstairs portion of the building is all yours. Location is prime as it is close to all things wonderful in Winter Park FL. Two streets behind is Lake Killarney. The space is beautifully decorated and offers guests a charming get away. Please note: It is a 13.6 mile drive (21 - 40 minutes depending on traffic) from Universal Studio's and a 21.7mile drive (24 - 45 minutes depending on traffic) to Disney World. There is a lock box located under the stairwell on the left side of the building. I will message you with your code for access. Once you get your key, head on up the stairs and enjoy your home away from home. Welcome! I live 3 minutes away from the Air BnB property and I work in the downstairs portion of the building, so I am local and available to assist with any additional requests. Message me anytime! Or text 407 575 3502 The Fairbanks corridor of Winter Park is the main artery to affluent areas, offering great shopping and dining close by. This hidden gem is a short walk to grocery stores, restaurants, and Winter Park Village shopping district with its movie theater. Light sleepers, please be aware that there is the potential for traffic noise. The BnB offers a large parking lot. You should have no problem at all if you desire to arrive by car. The area is also safe to bike around and Uber or Lyft operates in the area. No smoking please.

Apr 16 – 23

G$23,907 GYD per night

Guest favorite

Bungalow in Winter Park

4.98 out of 5 average rating, 235 reviews

Cozy 2/2 Bungalow - Downtown Winterpark/Orlando

Your family will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, you will be 5 minutes from Downtown Orlando and Downtown Edgewater, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! College Park local parks and golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music

Jun 10 – 17

G$27,405 GYD per night

Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 303 reviews

A SUITE RETREAT with a Garden View in the City

A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

Jun 9 – 16

G$15,748 GYD per night

Guest favorite

Home in Winter Park

4.9 out of 5 average rating, 135 reviews

Guest Suite in Winter Park/Orlando

This private guest suite is next to our home but completely exclusive with a separate entrance, private bathroom and no access to the main house. The layout is like a studio apartment with a bedroom, dining area and kitchenette. Outside there is also a patio area for guests. Full Sail University- 1 mile University of Central Florida- 7 miles Orlando Int'l Airport - 11 miles Universal Studios- 18 miles Disney World- 23.8 miles Camping World Stadium- 10 miles Kia Center- 9 miles Downtown-8 miles

Jun 14 – 21

G$15,111 GYD per night

Guest favorite

Bungalow in Maitland

4.86 out of 5 average rating, 493 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Aug 11 – 18

G$20,602 GYD per night

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 317 reviews

St. Augustine suite

Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

Sep 12 – 19

G$19,384 GYD per night

Guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 288 reviews

Oasis Garden Cottage -cozy, chic, near everything!

Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

Aug 22 – 29

G$20,456 GYD per night

Guest favorite

Home in Maitland

4.97 out of 5 average rating, 118 reviews

The Butterfly Bungalow near Park Ave

This 1950s bungalow has been lovingly restored to maintain it's Florida charm and offer simple comforts. Located in a family-friendly neighborhood just a few blocks from the Enzian Theater, the bungalow is close to restaurants and shops lining the cobblestone streets of Park Ave, and centrally located to historic areas of both Winter Park and Maitland. Park Ave shopping district - 1.5 miles Whole Foods - 0.8 miles Publix - 0.8 miles SunRail - 1.7 miles Downtown Orlando - 8 miles

Oct 23 – 30

G$27,970 GYD per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 639 reviews

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

Dec 5 – 12

G$24,737 GYD per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 227 reviews

Bungalow Near Downtown Orlando - No Cleaning Fee!

🌟 Newly Renovated Gem! 🏡 Nestled behind our 1950’s bungalow in Downtown Orlando's charming College Park district. Explore urban living with a small-town vibe! 🚲 Bike along brick tree-lined streets to award-winning restaurants, boutique shops, local breweries, and vibrant farmers markets! Nearby: 🌳 Winter Park: 10 mins 🏙️ Downtown Orlando: 10 mins 🛣️ I4: 2 mins 🏰 Disney and Universal: 20-30 mins 🏥 Hospital: 5 mins Experience the best of Orlando just moments away! ✨

May 11 – 18

G$24,660 GYD per night

Guest favorite

Guesthouse in Winter Park

4.98 out of 5 average rating, 250 reviews

Private and Peaceful with Full Kitchen

Welcome to our spacious, secure getaway tucked in a quiet Winter Park neighborhood. Enjoy full kitchen, hardwood floors, high ceilings, superfast WiFi and lots of TV steaming options, walk-in closets and walk-in shower. The hosts live in a separate space attached to the house. Your suite and patio are completely private. Please register all guests when making your reservation. For everyone’s safety, we ask that there be no visitors besides registered guests.

Jul 25 – Aug 1

G$20,588 GYD per night

Superhost

Apartment in Maitland

4.81 out of 5 average rating, 264 reviews

At Mine | Elegant Double Suite in North Orlando

Experience ultimate comfort at our Maitland, FL hotel, ideally located just north of Downtown Orlando. we're the area's largest hotel. Enjoy the convenience and luxury of plush bedding, modern furnishings, and upscale Grohe showers in your room. Relax by our outdoor pool, keep fit in the 24-hour gym, and access the Genesis Health Club. With over 15,000 square feet of event space, secure parking, and free Wi-Fi, we've got you covered.

Jun 7 – 14

G$17,331 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Maitland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Maitland's top sights

Lake Lily Park8 locals recommend

ANTONIO'S Maitland16 locals recommend

Enzian Theater77 locals recommend

Kraft Azalea Gardens26 locals recommend

Luke's Kitchen and Bar14 locals recommend

Francesco's Ristorante & Pizzeria7 locals recommend

Other great vacation rentals in Maitland

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 155 reviews

The Sacred Space Downtown Orlando Milk District

Aug 15 – 22

G$22,077 GYD per night

Guest favorite

Guest suite in Altamonte Springs

4.92 out of 5 average rating, 316 reviews

The Bungalow

Jul 8 – 15

G$21,624 GYD per night

Guest favorite

Home in Maitland

4.94 out of 5 average rating, 148 reviews

Orlando area pool home in Maitland

Apr 8 – 15

G$43,451 GYD per night

Guest favorite

Apartment in Altamonte Springs

4.9 out of 5 average rating, 187 reviews

Altamonte Oak Tree Haven

Aug 22 – 29

G$16,662 GYD per night

Guest favorite

Home in Apopka

4.96 out of 5 average rating, 193 reviews

Farm feel in the city

Apr 22 – 29

G$24,315 GYD per night

Guest favorite

Bungalow in Altamonte Springs

4.87 out of 5 average rating, 328 reviews

Villa Mariana - Private & Cozy!

Sep 21 – 28

G$15,028 GYD per night

Guest favorite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 793 reviews

TreeHouse in the Cloud, (Close toTheme Parks

Apr 14 – 21

G$35,022 GYD per night

Guest favorite

Guesthouse in Orlando

4.91 out of 5 average rating, 145 reviews

8th Green Cottage - A relaxing oasis in the city

Oct 11 – 18

G$28,064 GYD per night

Show all

Quick stats about vacation rentals in Maitland

Total rentals
80 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
3.2K reviews

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 40 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 20 homes with wifi, over 20 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, 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.
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.

Vacation rentals in Maitland

Top-rated vacation rentals in Maitland

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Maitland vacation rentals

Stay near Maitland's top sights

Other great vacation rentals in Maitland

Guesthouse in Orlando

Guest suite in Altamonte Springs

Home in Maitland

Apartment in Altamonte Springs

Home in Apopka

Bungalow in Altamonte Springs

Treehouse in Saint Cloud

Guesthouse in Orlando

Quick stats about vacation rentals in Maitland

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Maitland?

Do apartment rentals in Maitland have air conditioning?

Do house rentals in Maitland have a kitchen?

What are the most popular amenities for Apartment Rentals in Maitland?

Are there family-friendly vacation rentals in Maitland?

Are there Maitland vacation rentals on Airbnb with pools?

Are there pet-friendly vacation rentals in Maitland?

Do apartment rentals in Maitland have wifi?

Destinations to explore