House vacation rentals in Winter Springs

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Top-rated house rentals in Winter Springs

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Guest favorite

Home in Sanford

4.92 out of 5 average rating, 194 reviews

Farmhouse-Chic Retreat with a Charming Patio

Guests have full use of the house, including a spacious kitchen. Four bedrooms with memory foam mattresses ensure you can sleep comfortably. The dining room table can seat 6-8. In the living room there’s a comfortable seating area across the room from a large desk - great for those traveling for work! There is a separate laundry room off the back patio. Guests will have complimentary use of detergent. Iron and ironing board are also available for guest use. On the property there’s an occupied mother-in-law apartment - with separate parking and it’s own entrance so that guests staying in the house are not disturbed by the apartment’s full-time occupant. The backyard is also has a dividing fence for house guests’ privacy. As a guest staying at the house you will have privacy, but I’m local nearby and can assist guests at their request. Behind the house is an occupied apartment that has its own entrance, parking, and backyard. Nestled into a cluster of moss-draped oaks, the house is only a short drive from restaurants and shops in Lake Mary and quaint downtown Sanford. The best way to navigate the area is by car. There are several car rental agencies nearby, with the Orlando-Sanford International Airport just 5-7 min drive.

Oct 16 – 23

G$39,343 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

Aug 7 – 14

G$14,676 GYD per night

Guest favorite

Home in Lake Mary

4.83 out of 5 average rating, 257 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 18 – 25

G$30,911 GYD per night

Guest favorite

Home in Sanford

4.97 out of 5 average rating, 212 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.

Apr 21 – 28

G$21,353 GYD per night

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 277 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.

Jul 24 – 31

G$44,042 GYD per night

Guest favorite

Home in Sanford

4.96 out of 5 average rating, 139 reviews

The Sanford Bokey Pokey

The residents of historic Sanford call themselves “Bokeys”. No one is sure of the exact origin of the name, but it has come to define the vibrant culture of Sanford’s people and unique historic charm. Welcome to the Bokey Pokey! This home away from home offers comfortable living space with two bedrooms and one bath. Each bedroom has a comfortable queen size mattress. A separate living room with a large wall mounted smart TV, abuts the fully stocked kitchen to provide a cozy like living space.

Jun 18 – 25

G$23,799 GYD per night

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 117 reviews

3/1 house conveniently located in central Florida!

Relax with your whole family in this peaceful quiet home. Your home away from home is Conveniently Located close to all the attraction and beaches. It's a small 800 sq ft 3 bed 1 bath House with Casper beds and flat screen in every room. The house was just renovated in 2022. 10 Minutes away from the Altamonte Springs hospital. Full Stocked kitchen with everything you need to cook a home cooked meal. It's a perfect place to stay with your family instead of a Hotel for a more comfortable stay.

Aug 15 – 22

G$26,001 GYD per night

Guest favorite

Home in Sanford

4.97 out of 5 average rating, 152 reviews

Famous Tiny Houseboat Historic Downtown Sanford FL

The Famous Tiny Houseboat named ‘Downtown Dharma’ is a gorgeous floating houseboat parked at the Monroe Harbour Marina in beautiful Historic Downtown Sanford, Florida just 20 minutes North of Orlando FL. It was made famous after being built on HGTV’s Tiny House Hunters TV show in Season 4, Episode 12. Over 500 sq ft, entire house on the water, full bath, kitchen, living room, bedroom, chill space (extra couch for tiny person) and porch. Super unique and cool space you're sure to love!

Aug 26 – Sep 2

G$33,595 GYD per night

Guest favorite

Home in Winter Park

4.94 out of 5 average rating, 112 reviews

Modern, Quiet & Cozy - Entire house /Winter park

Embrace Tranquil Living in Winter Park, Florida. Located in a quiet neighborhood NE of downtown this recently renovated house is modern, clean, and cozy. Short drive to other great attractions in Orlando. Its central location is minutes away from Park Ave, the University of Central Florida, Rollins College, Full Sail University, Downtown Orlando, MCO Airport, Amway Center, Dr. Phillips, Science Center, Orlando City Stadium, and much more! You need to be at least 18 years old to book.

Oct 20 – 27

G$33,168 GYD per night

Guest favorite

Home in Oviedo

4.96 out of 5 average rating, 228 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 1 – 8

G$24,367 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

Jan 15 – 22

G$27,959 GYD per night

Guest favorite

Home in Sanford

4.86 out of 5 average rating, 214 reviews

Private Pool at Flamingo Cottage

This 3 bedroom, 1.5 bath is equipped for a peaceful stay! A mile off I-4 & SR417, under 40 miles from Disney & Parks, close to shopping & transportation, a screened private pool, a backyard, 2-car garage, cable, wi-fi, new appliances, fully equipped, renovated kitchen, a washer and dryer. Inside, tile floors keep allergens at bay. An older home set up to be comfy and homey. Vacation in a home setting! With outdoor seating and citrus trees, Florida is at your doorstep!

Dec 26 – Jan 2

G$32,881 GYD per night