Winter Springs vacation rentals

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Top-rated vacation rentals in Winter Springs

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

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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 22 – 29

G$23,757 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

Jun 13 – 20

G$18,279 GYD per night

Guest favorite

Bungalow in Maitland

4.86 out of 5 average rating, 488 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.

Sep 20 – 27

G$19,106 GYD per night

Guest favorite

Home in Sanford

4.97 out of 5 average rating, 208 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.

Oct 2 – 9

G$21,401 GYD 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**

Jun 26 – Jul 3

G$18,598 GYD per night

Guest favorite

Guest suite in Oviedo

4.91 out of 5 average rating, 313 reviews

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and guests have complete privacy. There are no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge , microwave, TV, Wifi and access to non-heated swimming pool. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Universal Theme Parks: 27 miles Disney: 40 miles

Mar 15 – 22

G$22,658 GYD per night

Guest favorite

Guesthouse in Sanford

4.95 out of 5 average rating, 225 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

Jan 12 – 19

G$19,591 GYD per night

Guest favorite

Home in Oviedo

4.96 out of 5 average rating, 226 reviews

Cute cottage near UCF & trails. No cleaning fee

Our cottage is nestled behind Oviedo’s oldest home. The cottage boasts lots of windows with a beautiful view of the outdoors. Inside the cottage is a queen-size bed, table for 2-4, kitchenette with refrigerator, toaster and microwave, TV with Netflix and Prime, plus WiFi. There is a tall claw foot tub which can be difficult for people with mobility issues. The cottage is connected to the main house but has its own entrance and guests have complete privacy. There are no shared spaces.

Feb 2 – 9

G$23,486 GYD per night

Guest favorite

Guesthouse in Oviedo

4.95 out of 5 average rating, 242 reviews

Gated Luxury Country Home on Private 35 Acres

Unique 800 sq. ft standalone guesthouse on 35 private wooded acres. Relax in peace and quiet either outside with the beautiful scenery or inside with our professional GoldenWest 9' pool table. Fully furnished backyard patio with grill and smoker, firepit for cold evenings, kerosene lamps for ambiance, and lounge furniture for finishing that book you've been putting off. Conveniently located minutes away from 417, you are within reach of all that Orlando has to offer! NO CLEANING FEES!

Oct 3 – 10

G$21,305 GYD 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.

May 20 – 27

G$20,533 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!

Aug 27 – Sep 3

G$21,635 GYD per night

Guest favorite

Guest suite in Winter Springs

4.9 out of 5 average rating, 112 reviews

Sierra Suite w/ Pool, Hot tub, and Sauna-Near UCF

Welcome to your home away from home! Our 1 bedroom, 1 bathroom suite offers all the amenities you need for a comfortable and relaxing stay. Enjoy a dip in the pool, soak in the hot tub, or unwind in the sauna. The bedroom has a comfortable queen size bed, and the bathroom has a shower and tub. The suite is perfect for couples or solo travelers looking for a tranquil getaway. We look forward to hosting you!

Nov 6 – 13

G$19,128 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Springs vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Winter Springs's top sights

Oviedo Mall16 locals recommend

Townhouse Restaurant15 locals recommend

Regal Oviedo Mall10 locals recommend

Target6 locals recommend

Spring Hammock Preserve6 locals recommend

Publix Super Market at Winter Springs Town Center3 locals recommend

Other great vacation rentals in Winter Springs

Guest favorite

Home in Winter Park

4.9 out of 5 average rating, 132 reviews

Guest Suite in Winter Park/Orlando

Jul 19 – 26

G$18,251 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!

Jan 11 – 18

G$23,863 GYD 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

Jul 27 – Aug 3

G$28,944 GYD per night

Guest favorite

Guesthouse in Winter Park

4.82 out of 5 average rating, 234 reviews

WELCOME HOME IN WINTER PARK

Mar 15 – 22

G$21,451 GYD per night

Guest favorite

Guesthouse in Maitland

4.98 out of 5 average rating, 115 reviews

Private 1-bd Mid-Century Guesthouse

Dec 17 – 24

G$20,674 GYD per night

Guest favorite

Apartment in Sanford

4.97 out of 5 average rating, 206 reviews

The Carriage House Studio Apartment

Oct 26 – Nov 2

G$16,818 GYD per night

Guest favorite

Home in Maitland

4.97 out of 5 average rating, 115 reviews

The Butterfly Bungalow near Park Ave

Jul 30 – Aug 6

G$27,896 GYD per night

Guest favorite

Guest suite in Chuluota

4.99 out of 5 average rating, 499 reviews

Enjoy Our Beautiful Sunsets and Peaceful Sunrises

Aug 14 – 21

G$12,440 GYD per night

Show all

Other great vacation rentals in Winter Springs

Guest favorite

Guest suite in Winter Springs

4.97 out of 5 average rating, 66 reviews

Modern Guest Studio 15 mins from SFB Airport

Nov 16 – 23

G$16,327 GYD per night

Guest favorite

Home in Winter Springs

4.96 out of 5 average rating, 25 reviews

Just like home-specious 4 bedroom

Aug 6 – 13

G$45,597 GYD per night

Guest favorite

Guesthouse in Longwood

4.89 out of 5 average rating, 28 reviews

Cozy and Modern Studio suite in Longwood

Aug 1 – 8

G$15,781 GYD per night

Guest favorite

Guesthouse in Lake Mary

4.98 out of 5 average rating, 63 reviews

Cozy Cottage in the heart of Lake Mary

Jun 21 – 28

G$19,870 GYD per night

Guest favorite

Home in Longwood

4.9 out of 5 average rating, 58 reviews

Peaceful retreat family friendly home with parking

Dec 15 – 22

G$29,697 GYD per night

Guest favorite

Home in Maitland

5.0 out of 5 average rating, 22 reviews

Fern Park Retreat

May 5 – 12

G$24,702 GYD per night

Guest favorite

Home in Casselberry

5.0 out of 5 average rating, 42 reviews

Spacious 3 BR Home Perfect for Orlando Getaway

Jan 3 – 10

G$35,654 GYD per night

Guest favorite

Apartment in Orlando

5.0 out of 5 average rating, 67 reviews

Parent's Retreat!

Aug 2 – 9

G$23,517 GYD per night

Show all

Quick stats about vacation rentals in Winter Springs

Total rentals
80 properties
Rentals with a pool
20 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
2.9K reviews
Nightly prices starting at
G$2,084 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winter Springs?
Yes! Work meets play with ease at over 30 vacation rentals in Winter Springs featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winter Springs?
Four-legged friends are welcome in Winter Springs. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there Winter Springs vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Winter Springs, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in house rentals in Winter Springs?
Experience the best of Winter Springs 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 Winter Springs have wireless internet?
Absolutely! We offer over 50 house rentals with wireless internet in Winter Springs. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winter Springs?
Winter Springs has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winter Springs have air conditioning?
Absolutely! We offer over 50 house rentals with air conditioning in Winter Springs. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Winter Springs?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 50 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Winter Springs vacation rentals

Top-rated vacation rentals in Winter Springs

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Winter Springs vacation rentals

Stay near Winter Springs's top sights

Other great vacation rentals in Winter Springs

Home in Winter Park

Guest suite in Altamonte Springs

Guest suite in Lake Mary

Guesthouse in Winter Park

Guesthouse in Maitland

Apartment in Sanford

Home in Maitland

Guest suite in Chuluota

Other great vacation rentals in Winter Springs

Guest suite in Winter Springs

Home in Winter Springs

Guesthouse in Longwood

Guesthouse in Lake Mary

Home in Longwood

Home in Maitland

Home in Casselberry

Apartment in Orlando

Quick stats about vacation rentals in Winter Springs

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 vacation rentals with a dedicated workspace in Winter Springs?

Are there pet-friendly vacation rentals in Winter Springs?

Are there Winter Springs vacation rentals on Airbnb with pools?

How much does it cost to stay in house rentals in Winter Springs?

Do house rentals in Winter Springs have wireless internet?

Are there family-friendly house rentals in Winter Springs?

Do house rentals in Winter Springs have air conditioning?

What are the most popular amenities for House Rentals in Winter Springs?

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