Vacation rentals in Lake Mary

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Top-rated vacation rentals in Lake Mary

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

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Guest favorite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.87 out of 5 average rating, 592 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.

Top guest favorite
A compact space features a trundle bed topped with a floral comforter and decorative pillows. Framed artwork adorns the wall above, while a small dining table for two is positioned nearby. A kitchenette with a microwave and refrigerator is visible, with natural light streaming through the window.
Tiny home in Apopka
4.97 out of 5 average rating, 248 reviews

Tiny Home Near the Springs

Fresh air and back to nature. Imagine a tiny but comfortable hotel room in a rural setting. You'll hear roosters crow as the sun rises. Take a walk on a moonless cloudless night, and you may see stars. This 190 sq. ft. tiny house is a ten minute drive to either Rock Springs or Wekiva Springs, a four minute bike ride to the West Orange Trail which runs for 22 miles, and a 15 minute drive to the Lake Apopka Wildlife Drive. The major theme parks are a 30 to 45 minute drive, depending on traffic.

Top guest favorite
A studio-style living space features a spacious bed with neutral bedding, complemented by decorative pillows. A round mirror hangs over a wooden nightstand. The kitchenette area includes a small microwave and cabinetry, while an area rug adds warmth to the wooden floor.
Guest suite in Sanford
4.98 out of 5 average rating, 246 reviews

The Secret Sanctuary in Sanford, 5min from Airport

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**

Top guest favorite
A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.
Guesthouse in Longwood
4.98 out of 5 average rating, 123 reviews

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

Guest favorite
A well-manicured pathway leads to the studio, surrounded by lush greenery and colorful plants. Visible are large windows framed by white curtains, providing a view of the scenic lake. A patio with a red umbrella and a picnic table is accessible for outdoor relaxation.
Guesthouse in Lake Mary
4.94 out of 5 average rating, 108 reviews

Nature Unique lake view Tiny Guest studio

Tiny Guest house studio with separate entrance for privacy and amazing Lake view. Unlimited rental of 2 Blue kayaks included during stay!! Walking distace from windixie supermarket, downtown lake Mary, restaurants, shopping centers, entertainment and dunking Donuts. Common areas outside studio are shared. Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl. 30 min to Daytona Beach. Near Wekiva springs. To go to Disney, easy access to I-4 and 4-17.

Guest favorite
Guesthouse in Sanford
4.94 out of 5 average rating, 180 reviews

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a private studio guest house with its own entrance, features full kitchen & bath room, queen size bed, full size pull out couch & twin size travel bed, & provides flexible self check-in. We are located 7 minutes from the Sanford Airport and Boombah Sports Complex, 10 minutes to Downtown Sanford, I –4 & 4–17. We’re also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts

Top guest favorite
A serene view of Lake Mary is framed by a large tree and a white post. The sky transitions into vibrant hues as the sun sets, reflecting softly on the water's surface. A lamp illuminates the foreground, enhancing the peaceful lakeside atmosphere.
Guesthouse in Lake Mary
4.97 out of 5 average rating, 127 reviews

Sunset Cottage in Lake Mary, Florida

Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

Top guest favorite
The spacious room features a queen bed dressed in crisp white linens, flanked by two blue accent chairs. A large area rug adds comfort underfoot. Natural light streams in through a nearby window, and a ceiling fan provides a cooling breeze. A small dining area is also visible.
Guesthouse in Sanford
4.94 out of 5 average rating, 125 reviews

Suite Retreat

Avoid blah hotels with high prices and stay in this luxe new apartment suite! It’s a perfect retreat in Central Florida. Located a short drive to activities, restaurants, & shops in Lake Mary or downtown Sanford - 45-55 min to Orlando theme parks or the beaches of New Smyrna. Ideal for a couple’s retreat or a getaway for one. Guests use office space designed for comfort & productivity. A cozy chair begs readers to curl up and read. The outdoor canopy hosts breakfast with birdsong!

Top guest favorite
An iron gate stands at the entrance of a private driveway, flanked by brick pillars. Lush greenery surrounds the path, leading to a bright, open area in the distance, suggesting a tranquil and secluded setting.
Guest suite in Sanford
4.91 out of 5 average rating, 457 reviews

Sanford airport/lakehouse/Boombah/venue1902

This Silver Lake Estate is perfect for a quick getaway. Located 1 mile from Sanford airport,1 hour from Disney,40 min to the Atlantic Ocean and 10 min drive to the activities of Lake Monroe. With 8 mile bike/walk riverwalk,marina,zoo,restaurants & microbrews. 2bed ,1 bath, private patio & entrance. With coffee maker,toaster oven,microwave,mini fridge(no kitchen)paddle boards,kayaks,and fishing. Discounts available on nonrefundable cancellations. No more than 4 guests at anytime!

Guest favorite
A spacious pool area is surrounded by tropical landscaping, featuring tall palm trees and flourishing plants. The pool includes a spa with cascading water features. A bright red umbrella provides shade over a seating area, creating an inviting outdoor space for relaxation.
Home in Lake Mary
4.9 out of 5 average rating, 272 reviews

Gated community XL pool Home 2500sq/f

Our LK Mary home sits in Between the 2 most famous places central Florida has to offer, Disney World & Daytona beach and everything else in between. This property sits on 1/2acre of land, tropical landscaped backyard making your stay with us the true Floridian experience . Total privacy with quite nights for a full rest. NO BIKERS PLease! My home is in a Gated community.1 mile to Dtwn Lake Mary. Our pool is NOT heated, the hot tub only CAN be headed at an additional cost

Top guest favorite
A welcoming living area features comfortable seating arrangements around a central ottoman. A large television is placed on a stylish console, with decorative plants and artwork enhancing the space. Natural light streams through windows, contributing to a bright, inviting environment.
Home in Sanford
4.99 out of 5 average rating, 156 reviews

The Cypress House

This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb

Guest favorite
A vibrant blue tiny home with a welcoming front porch is surrounded by lush greenery. Two white chairs are positioned on the wooden deck, inviting relaxation. Large windows allow natural light to fill the interior, while a light fixture hangs above the entrance.
Tiny home in Chuluota
4.93 out of 5 average rating, 155 reviews

Tiny Tropical House! 🏝

Welcome to life on Tropical ! Our tiny home is located right outside of Oviedo. About 20 mins away from UCF and an hour from Cocoa and most major theme Parks. We live down the street from Lake Mills Park which is a beautiful park with a great lake you are welcome to use our water crafts too! *Please note that the ladder to access the loft above the restroom is not secured to the wall and is moveable. If you proceed to book use at your own risk.

Popular amenities for Lake Mary places to stay

When is the best time to visit Lake Mary?

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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Lake Mary?

    Yes! Work meets play with ease at over 30 vacation rentals in Lake Mary featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Lake Mary?

    Experience the best of Lake Mary with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Lake Mary?

    Four-legged friends are welcome in Lake Mary. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there Lake Mary vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Lake Mary, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly house rentals in Lake Mary?

    Lake Mary has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Lake Mary have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Lake Mary. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lake Mary have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Lake Mary. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Lake Mary?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Lake Mary

  • Total vacation rentals

    Explore 60 vacation rentals in Lake Mary

  • Nightly prices starting at

    Lake Mary vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 3,420 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Lake Mary vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Lake access, Gym, and BBQ grill across Lake Mary rentals

  • 4.9 Average rating

    Lake Mary stays are highly rated by guests—averaging 4.9 out of 5!

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