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, 282 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.

Aug 28 – Sep 4

G$23,764 GYD per night

Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 302 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

May 11 – 18

G$15,420 GYD per night

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 141 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

Enjoy a stylish guest experience at this centrally-located Altamonte Springs Florida guest suite. This luxury 830 sq ft unit offers a living room, kitchenette, bedroom, bathroom and large pool in the peaceful Spring Valley Farms residential community. It is located 8 miles north of downtown Orlando, a primo location close to downtown, both ocean coasts, Wakiwa Springs State Park, theme parks (Disney, Universal, SeaWorld, more), Crane's Roost, and many other great destinations in central Florida!

Nov 12 – 19

G$25,399 GYD per night

Guest favorite

Bungalow in Winter Park

4.98 out of 5 average rating, 232 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

Sep 13 – 20

G$29,134 GYD per night

Guest favorite

Guest suite in Altamonte Springs

4.97 out of 5 average rating, 300 reviews

St. Hemingway Suite

Very tranquil Romantic room with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you to Spring Valley

Jul 27 – Aug 3

G$18,454 GYD per night

Guest favorite

Bungalow in Maitland

4.86 out of 5 average rating, 489 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.

Jun 27 – Jul 4

G$22,755 GYD per night

Guest favorite

Home in Maitland

4.97 out of 5 average rating, 115 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

May 8 – 15

G$27,903 GYD per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 636 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.

Jan 3 – 10

G$26,513 GYD per night

Guest favorite

Guest suite in Altamonte Springs

4.92 out of 5 average rating, 315 reviews

The Bungalow

Welcome to your home away from home! Enter through a private driveway and enjoy the ease of keyless entry. Located across the street, Sanlando Park offers walking trails, basketball and popular tennis courts. Whether your interests are peace and quiet or adventure, you are only 30 minutes or less away from our beautiful natural springs, beaches and all major attractions. Wake up with the sunshine, put on a pot of coffee and welcome to Florida!

May 15 – 22

G$21,539 GYD per night

Guest favorite

Guesthouse in Orlando

4.98 out of 5 average rating, 146 reviews

The Loft in College Park

The Loft is a private guesthouse located above our garage near Downtown Orlando and Ivanhoe Village. It is walking distance to multiple restaurants, bars and shops. Also close to I-4 and easy access to the attractions. The studio space offers a queen size bed as well as a queen size sleeper sofa in the living room area. Luxurious full size bathroom with walk in shower and rain shower head. Perfect get away for those looking to enjoy Orlando!

Aug 7 – 14

G$18,078 GYD per night

Superhost

Apartment in Maitland

4.81 out of 5 average rating, 178 reviews

At Mine | Spacious Double Suite in 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.

Sep 12 – 19

G$13,157 GYD per night

Guest favorite

Guesthouse in Maitland

4.87 out of 5 average rating, 381 reviews

Chez Bienvenu

Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space

Feb 24 – Mar 3

G$24,065 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

JazzTastings17 locals recommend

ANTONIO'S Maitland16 locals recommend

Enzian Theater77 locals recommend

Kraft Azalea Gardens26 locals recommend

Luke's Kitchen and Bar14 locals recommend

Other great vacation rentals in Maitland

Guest favorite

Bungalow in Altamonte Springs

4.87 out of 5 average rating, 327 reviews

Villa Mariana - Private & Cozy!

Jun 12 – 19

G$15,910 GYD per night

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 162 reviews

Treehouse Inn Downtown Orlando, 2 bedrooms 2 bath

Jul 3 – 10

G$24,263 GYD per night

Superhost

Guest suite in Maitland

4.8 out of 5 average rating, 5 reviews

Eulalia Quarter by Winter Park

Jul 20 – 27

G$18,397 GYD per night

Guest favorite

Home in Maitland

5.0 out of 5 average rating, 22 reviews

Fern Park Retreat

Aug 23 – 30

G$24,709 GYD per night

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 40 reviews

New Mid Century-Modern Studio

Jul 8 – 15

G$17,497 GYD per night

Guest favorite

Guest suite in Eatonville

4.99 out of 5 average rating, 69 reviews

Private entrance/bathroom 10 min from DT Orlando

Oct 11 – 18

G$11,980 GYD per night

Guest favorite

Home in Altamonte Springs

5.0 out of 5 average rating, 29 reviews

Orlando's Cozy & Private Studio Altamonte Springs

Jul 19 – 26

G$23,390 GYD per night

Guest favorite

Bungalow in Orlando

5.0 out of 5 average rating, 23 reviews

Cozy Cottage in College Park.

Oct 3 – 10

G$16,936 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 apartment rentals in Maitland have a kitchen?
Absolutely! We offer over 10 apartment 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 a kitchen, over 20 homes with wifi, over 10 homes with free parking, 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.
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

Bungalow in Altamonte Springs

Guesthouse in Orlando

Guest suite in Maitland

Home in Maitland

Guesthouse in Orlando

Guest suite in Eatonville

Home in Altamonte Springs

Bungalow 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 apartment 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