Vacation rentals in Longwood

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Top-rated vacation rentals in Longwood

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

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Guest favorite

Home in Lake Mary

4.83 out of 5 average rating, 253 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.

Nov 4 – 11

R2,817 ZAR 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!

Apr 23 – 30

R2,179 ZAR 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

Aug 6 – 13

R1,666 ZAR per night

Guest favorite

Bungalow in Maitland

4.86 out of 5 average rating, 490 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 14 – 21

R1,859 ZAR per night

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 274 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.

Sep 11 – 18

R3,438 ZAR per night

Guest favorite

Home in Sanford

4.97 out of 5 average rating, 210 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.

Dec 5 – 12

R1,954 ZAR per night

Guest favorite

Guest suite in Sanford

4.98 out of 5 average rating, 183 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**

Jul 1 – 8

R1,736 ZAR 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

Nov 14 – 21

R2,548 ZAR per night

Guest favorite

Guest suite in Lake Mary

4.96 out of 5 average rating, 286 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

Jul 19 – 26

R2,643 ZAR per night

Guest favorite

Guesthouse in Winter Park

4.98 out of 5 average rating, 249 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.

Jun 5 – 12

R1,875 ZAR per night

Guest favorite

Guesthouse in Maitland

4.98 out of 5 average rating, 116 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!

Dec 8 – 15

R1,844 ZAR per night

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 384 reviews

Guest Suite! Key West in Altamonte Springs!

This Beautiful Little Guest Suite on ground floor with courtyard entrance. Completely separate entrance and private from the main house. Beautifully decorated with four post queen shutter style bed, wet bar area with mini fridge, morning coffee bar, full bathroom with shower. Driveway parking. Walking distance to Altamonte Mall. 45 mins from Atlantic Coast. 35 mins to Disney Area Attractions.

Aug 25 – Sep 1

R1,944 ZAR per night

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

Big Tree Park6 locals recommend

BR Sushi (Longwood)7 locals recommend

Winn-Dixie53 locals recommend

Victorio's Oyster Bar & Grille3 locals recommend

Northland Church3 locals recommend

Other great vacation rentals in Longwood

Guest favorite

Guest suite in Altamonte Springs

4.92 out of 5 average rating, 315 reviews

The Bungalow

Jun 21 – 28

R2,047 ZAR per night

Guest favorite

Guest suite in Lake Mary

4.95 out of 5 average rating, 103 reviews

Quiet, Upscale Studio

Dec 27 – Jan 3

R1,844 ZAR per night

Guest favorite

Bungalow in Altamonte Springs

4.87 out of 5 average rating, 327 reviews

Villa Mariana - Private & Cozy!

Aug 6 – 13

R1,409 ZAR per night

Guest favorite

Guesthouse in Sanford

4.95 out of 5 average rating, 226 reviews

Palmetto Pool Retreat

Jan 16 – 23

R1,789 ZAR per night

Superhost

Apartment in Maitland

4.81 out of 5 average rating, 259 reviews

At Mine | Elegant Double Suite in North Orlando

Sep 14 – 21

R1,335 ZAR per night

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

Dec 8 – 15

R2,170 ZAR per night

Guest favorite

Tiny home in Lake Mary

4.95 out of 5 average rating, 195 reviews

Entire house, The Traveler (Tiny House)

May 22 – 29

R2,044 ZAR per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 637 reviews

The Little Treehouse 2 at Country Club of Orlando

Sep 23 – 30

R2,421 ZAR per night

Show all

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
R190 ZAR before taxes and fees

Frequently Asked Questions

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 air conditioning, over 70 homes with free parking, over 60 homes with a kitchen, over 70 homes with wifi, 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.
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.

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

Guest suite in Altamonte Springs

Guest suite in Lake Mary

Bungalow in Altamonte Springs

Guesthouse in Sanford

Apartment in Maitland

Apartment in Winter Park

Tiny home in Lake Mary

Tiny home in Orlando

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 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?

Are there Longwood vacation rentals on Airbnb with pools?

Are there pet-friendly vacation rentals in Longwood?

Destinations to explore