Vacation rentals in Longwood

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Top-rated vacation rentals in Longwood

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Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 143 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!

Guest favorite

Home in Lake Mary

4.83 out of 5 average rating, 260 reviews

Independent Unique Guest house lake/kayaks/jacuzzy

Independent Guest house with a beautiful lake where you can have unlimited kayaking use during your stay as option(2 kayaks). Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl, walking distance to windixie super market, downtown Lake Mary, dunking donuts , near Orlando Sanford International Airport. Walk to many restaurants and entertainment, 30 min to Daytona Beach. Near Wekiva springs. To go to Disney or Universal, we have easy access to I-4 and 4-17.

Guest favorite

Bungalow in Maitland

4.86 out of 5 average rating, 496 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.

Guest favorite

Home in Sanford

4.97 out of 5 average rating, 213 reviews

Clean, cozy home in a GREAT location

This clean, comfortable home is in a peaceful neighborhood and centrally located to everything you may wish to enjoy while on your Central Florida vacation. Literally two to three minutes away from I-4, highway 417 and a multitude of shopping and dining options. Universal Studios, Sea World and Daytona International Speedway are all within about 40 minutes, while Disney World and Kennedy Space Center are about 50 - 60 minutes. Also easy access to Sanford and Orlando International Airports.

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 280 reviews

Eclectic Home Where Luxury Meets Affordability

Welcome to the Haven at Temper Wild - Your home away from home. We offer fully free amenities, luxury bedding and pillows, and quintessential design throughout the rooms and home. There are work spaces in every bedroom, ultra-fast wifi, games galore, and a beautiful outdoor space equipped with outdoor dining and lounging. Pet Fee's per pet: $100 (You must notify host if you are bringing a pet prior to booking) Read the rules of the property before booking, to ensure that you are OK with them.

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 318 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

Guest favorite

Guest suite in Sanford

4.98 out of 5 average rating, 185 reviews

The Secret Sanctuary in Sanford

Welcome to your quiet, spacious, and private sanctuary. Enjoy all new appliances in the full size kitchen, a 50” flat screen TV, and a shaded outdoor area surrounded by greenery. It is located only minutes from the Orlando Sanford International Airport, Historic Downtown Sanford’s restaurants and shops, Lake Monroe’s scenic waterfront, and is centrally located between Florida’s beaches and the amusement parks. **Space is cleaned with EPA approved cleaners, including high touch surfaces**

Guest favorite

Guesthouse in Sanford

4.95 out of 5 average rating, 228 reviews

Palmetto Pool Retreat

The Palmetto Pool Retreat offers complete privacy - detached studio cottage, with a pull-down Queen Murphy bed. * Kitchen - refrigerator, stove, cookware, Keurig , microwave, toaster, dishes and utensils. * Studio Living area - Queen size Murphy Bed, Roku TV, WiFi Internet, AC/Heater; Closet, Iron. Please don’t put AC lower than 72. * Private Bathroom - shower, hairdryer. *Outdoors - Solar heated pool(not propane heated) with private sitting area with 2 Fire pits Gas & Wood; BBQ Gas

Guest favorite

Home in Maitland

4.97 out of 5 average rating, 121 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

Guest favorite

Guest suite in Lake Mary

4.96 out of 5 average rating, 289 reviews

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting

Guest favorite

Guest suite in Altamonte Springs

4.92 out of 5 average rating, 317 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!

Guest favorite

Guesthouse in Maitland

4.98 out of 5 average rating, 119 reviews

Private 1-bd Mid-Century Guesthouse

Welcome to our tranquil & private 1-bd Mid-Century Modern Guesthouse. The space has a separate entrance and keyless access. Full kitchen, living room, bedroom and bathroom. Centrally located in Florida, our guesthouse offers easy access to the surrounding areas. Lots of museums, nature walks, parks & fantastic places to eat. Book now & experience the love & care we have put into our property!

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Longwood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Longwood's top sights

Orlando Health South Seminole Hospital3 locals recommend

BR Sushi (Longwood)7 locals recommend

Winn-Dixie53 locals recommend

Victorio's Oyster Bar & Grille3 locals recommend

Northland Church3 locals recommend

Cubans on the Run3 locals recommend

Other great vacation rentals in Longwood

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 117 reviews

3/1 house conveniently located in central Florida!

Guest favorite

Guest suite in Lake Mary

4.95 out of 5 average rating, 105 reviews

Quiet, Upscale Studio

Guest favorite

Home in Sanford

4.92 out of 5 average rating, 195 reviews

Farmhouse-Chic Retreat with a Charming Patio

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

Guest favorite

Apartment in Altamonte Springs

4.89 out of 5 average rating, 189 reviews

Altamonte Oak Tree Haven

Guest favorite

Apartment in Sanford

4.97 out of 5 average rating, 210 reviews

The Carriage House Studio Apartment

Guest favorite

Guest suite in Sanford

4.91 out of 5 average rating, 380 reviews

Sanford airport/lakehouse/Boombah/venue1902

Guest favorite

Tiny home in Lake Mary

4.95 out of 5 average rating, 198 reviews

Entire house, The Traveler (Tiny House)

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Quick stats about vacation rentals in Longwood

Total rentals
90 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
3.2K reviews
Nightly prices starting at
$10 before taxes and fees

Frequently Asked Questions

Are there Longwood vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Longwood, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Longwood?
Four-legged friends are welcome in Longwood. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Longwood?
Longwood has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Longwood have free parking?
Absolutely! We offer over 70 house rentals with free parking in Longwood. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Longwood?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with free parking, over 60 homes with a kitchen, over 70 homes with wifi, over 70 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Longwood?
Yes! Work meets play with ease at over 40 vacation rentals in Longwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Longwood have wifi?
Absolutely! We offer over 70 house rentals with wifi in Longwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Longwood have a kitchen?
Absolutely! We offer over 60 house rentals with a kitchen in Longwood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Longwood?
Experience the best of Longwood with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Longwood have air conditioning?
Absolutely! We offer over 70 house rentals with air conditioning in Longwood. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Longwood

Top-rated vacation rentals in Longwood

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Longwood vacation rentals

Stay near Longwood's top sights

Other great vacation rentals in Longwood

Home in Altamonte Springs

Guest suite in Lake Mary

Home in Sanford

Apartment in Winter Park

Apartment in Altamonte Springs

Apartment in Sanford

Guest suite in Sanford

Tiny home in Lake Mary

Quick stats about vacation rentals in Longwood

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there Longwood vacation rentals on Airbnb with pools?

Are there pet-friendly vacation rentals in Longwood?

Are there family-friendly vacation rentals in Longwood?

Do house rentals in Longwood have free parking?

What are the most popular amenities for House Rentals in Longwood?

Are there vacation rentals with a dedicated workspace in Longwood?

Do house rentals in Longwood have wifi?

Do house rentals in Longwood have a kitchen?

How much does it cost to stay in house rentals in Longwood?

Do house rentals in Longwood have air conditioning?

Destinations to explore