Family-friendly holiday rentals in Sanford

Private Courtyard Cottage on Canal

Enjoy a comfortable stay in this private guest cottage with its own entrance, detached from the main house—perfect for privacy and relaxation. Features an extremely comfortable king-size bed, TV, and WiFi ideal for streaming or remote work. The kitchenette includes a full-size fridge, microwave, sink, air fryer, and coffee maker for easy meals and morning coffee. Ideal for couples, solo travelers, business stays, or sports families looking for a quiet, comfortable home base close to everything

The Blue Aztec

Premier location, steps away from historic downtown • 1 Queen Bed • Completely renovated apartment totally equipped for a short or long stay • Our goal is to exceed your expectations, provide a comfortable, personal experience, and give you the feeling that you are at home. • Lounge on the front porch, take a walk to the nearby dog park or walk down Sanford Ave right out your door (This unit is pet friendly but a non refundable pet deposit will apply. Ask for details.)

Sanford Rooftop Garden Apartment

An "old Florida" feel is combined with a private, modern, full kitchen; comfortable furnishings; and large decks with views of mature live oak trees and lush gardens in the expansive grounds and neighboring park; all in an old, friendly, safe, and quiet neighborhood. Walk, bike, or drive an easy 16 blocks to downtown Sanford past historic, renovated residences. Enjoy sightseeing along Lake Monroe, eclectic shopping, and dining and relaxing at the many restaurants, pubs, and microbreweries.

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**

The Bed & Brad

Kick back and relax in this calm, stylish space. Enjoy the splendors of Sanford’s historic district with its beautiful brick roads and magnificent oak lined streets dripping with southern Spanish Moss. Walk or ride to the downtown area where you can eat and drink till your hearts content. Enjoy a walk along the lake or stroll through the streets to look at glorious restored southern homes. The Bed & Brad offers you all the comforts of home where you can enjoy your stay at your own pace.

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.

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

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!

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.

Spotless New Home | 4 blocks to downtown

Take a step back in time at The Retro Retreat, where vintage charm meets modern comfort in this brand-new home. Nestled in a peaceful residential neighborhood, you're just steps away from downtown Sanford's vibrant restaurants, breweries, and charming boutiques. Enjoy the best of both worlds—only a 5-minute walk to local favorites, a relaxing 15-minute stroll to the scenic waterfront, a quick 5-minute drive to the airport, and just 30 minutes from Orlando.

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

Entire house, The Traveler (Tiny House)

Business or vacation plans bring you to sunny Florida and need a place to stay? Look no further than this Brand New Tiny Home with all of the modern amenities located in Lake Mary. Close to all the major Orlando attractions. The Traveler was built with your comfort in mind and includes: queen upstairs and a day bed with 2 twin size, kitchen , bathroom w/ shower and smart TV. Especially WiFi.