Family-friendly holiday rentals in Gainesville

4.93 out of 5 average rating, 101 reviews

The Glass House features a wooden deck with expansive glass doors, reflecting the warm hues of sunset. The structure is surrounded by large, moss-laden oak trees, contributing to a serene, natural ambiance.

Cottage in Archer

The Glass House

*WIFI Now Available * The Glass House was built by local artist, Ira Winarsky. A charming cottage nestled on 12.5 acres just 7 miles from Gainesville. This cozy fully air-conditioned, retreat offers a perfect blend of nature and comfort, featuring a full kitchen, living room, and spacious deck with scenic views for an evening under the stars. Ideal for couples, adventurers, birdwatchers and Gator friends and fans alike. Seeking a peaceful escape? Come unwind and recharge. *LAKE IS CURRENTLY DRY

Shipping container in Gainesville

An open loft-style space contains a spacious bed with decorative pillows. Light wood flooring and colorful rugs add warmth. Natural light filters in through nearby windows. A small desk and shelves create an inviting area for work or relaxation, complemented by tasteful artwork on the walls.

4.98 out of 5 average rating, 890 reviews

Unique Container "Caja Verde" 1 Mile UF & Downtown

Our home is less than a mile to UFHealth at Shands and the Malcom Randall Veterans Medical Center. We are a mile to the University of Florida campus. Amazingly, also a short bike ride (1-2 miles) to Downtown Gainesville. Close to Depot Park, art studios, restaurants, music venues, and theater. Nature parks close too. The bonus is we live on 2 acres, tucked back in a quiet neighborhood. Our pool is deep & cool; we have bikes to borrow. The container is perfect for a solo traveler, or a couple.

4.98 out of 5 average rating, 150 reviews

A light-filled living room features a green tufted couch and a glass coffee table. A tasteful wall art piece adds a touch of style. Natural light filters in through multiple windows, illuminating the warm wooden floors and showcasing the inviting atmosphere.

Flat in Gainesville

Trendy Apartment in Historic Downtown Duck Pond

Welcome to your serene, green retreat! This newly redecorated trendy space was created with your comfort in mind. Beautiful furniture, artwork, superior quality king mattress and linens will allow you to fully relax and rejuvenate. With a fully equipped kitchen, you'll have everything you need for an easy and rejuvenating getaway. Free "guest only" parking and Tesla 44 mile per hour charging. We installed a 2 ton Trane AC exclusively in this apartment June 2024 to guarantee your comfort.

4.95 out of 5 average rating, 163 reviews

Cozy Cottage. Near Downtown & UF.

Welcome to The Cozy Cottage, where you'll experience the charm of a 1950's home infused with the essence of Hygge. Embrace the bright and cozy vibes, and delight in the simple pleasures of life. Nestled on a corner quarter acre lot, our lovely house is conveniently close to the University of Florida and downtown 5min Curia on the drag 6 min from Downtown 10 min from UF 12 min from Shands hospital 30 min to Ginnie springs 20 min from Gainesville airport 20 min from Gainesville raceway

4.94 out of 5 average rating, 103 reviews

Cozy 1930s Cottage Walk to Downtown + Grove Street

Stylish cottage in the heart of Gainesville's historic Pleasant Street. 3 min walk to dining and shops. 5 min walk downtown. 1 mile to UF campus. This fully renovated 1930s cottage has vintage charm with modern comfort. Brand new appliances, comfy beds, Smart TVs, and stylish furniture complement the original clawfoot tub, beadboard walls & hardwood floors. Relax or dine on the spacious deck, or let your dog roam the fully fenced yard or park. Up to 2 pets welcome with a $40 fee

Guest house in Gainesville

The exterior of the loft showcases a charming A-frame structure, accentuated by wooden beams and a warm glow from the illuminated windows. Soft string lights create an inviting atmosphere around the pathway, which is framed by lush greenery and leads to a shared firepit.

4.95 out of 5 average rating, 304 reviews

Walk to UF! Historic King Bed Loft w/ Private Deck

If you are visiting Gainesville, look no further than Camellia Loft. This historic gem was built in 1924 and has been freshly renovated to bring it into the modern era. Enjoy the birdsong and majestic trees from your private deck overlooking the backyard—or relax inside as light streams through the loft's massive skylights. Only 0.5 miles to UF campus and exactly 1 mile to the stadium, you can easily walk to campus or games. Unwind by the shared fire pit or enjoy cooking on the grill

Guest house in Gainesville

A cozy bedroom features a spacious bed with crisp white linens and a soft beige throw. An air conditioning unit is mounted above, while a bedside lamp provides gentle lighting. A door leads to a full bathroom, visible in the background.

4.92 out of 5 average rating, 100 reviews

Palm N' Pillow • Guesthouse by UF, HCA-FL & Shands

Private, fully furnished guesthouse in a prime location—just 7 mins to UF Shands & HCA hospitals. 1BR w/ queen bed, full bath, pull-out couch, air mattress (sleeps 5). Full kitchen w/ cookware, in-unit washer/dryer, fast Wi-Fi, TV, dining & chill patio. Ideal for medical professionals, families, or extended stays. Safe neighborhood with quick access to shopping, dining & downtown. Comfort, privacy, and convenience. Free parking included. No smoking or vaping allowed—strict fines apply.

The entrance of the property features a welcoming pathway lined with greenery. Flanking the path are shrubs and small plants, while a neutral-colored facade is complemented by large windows, allowing natural light to illuminate the interior.

4.89 out of 5 average rating, 182 reviews

The Tree House - Nicely Furnished Urban Oasis

Welcome to the Tree House. Airy and bright spaces invite to a peaceful stay in this green oasis in SW Gainesville. Perfect for families or group of friends. The house has a well equipped kitchen, a spacious dining area and a cosy living room made for relaxing and game nights incl. a sofa bed. Bedrooms come with comfy queen-sized beds and the primary bedroom has an ensuite. Close to UF (7mins), stadium (10mins), hospitals and downtown (>15mins), I75 for a quick escape into nature.

Guest house in Gainesville

A well-appointed sleeping area features a spacious bed dressed in light gray bedding, flanked by two bedside tables with stylish lamps. Colorful wall art complements the space, while natural light streams through several textured windows, enhancing the tranquil ambiance.

4.97 out of 5 average rating, 644 reviews

Stylish Private Studio | Walk to UF

NEWLY RENOVATED | WALK TO UF | PRIVATE STUDIO Wake up minutes from campus in a light-filled, mid-century modern studio — just 0.5 miles from UF. Perfect for game days, campus visits, graduations, and hospital stays (2 miles to UF Health Shands & HCA). This private, detached guest house features modern finishes, natural light, a comfortable bed, kitchenette, mini fridge, Smart TV, fast WiFi, and a workspace. Quiet, central location near UF and downtown Gainesville.

The living area features a spacious white-sectional sofa adorned with neutral-toned throw pillows and soft blankets. A rustic coffee table sits in the center, flanked by decorative floral arrangements. Large windows allow natural light to illuminate the space, while a serene outdoor view is visible.

4.92 out of 5 average rating, 173 reviews

Modern Muse w/Firepit, Salt Pool and Cabanas

Enjoy a Luxury stay for your next getaway. This MODERN PARADISE provides you everything and more. All lighting, TV’s and Living Area surround sound (Sonos) are Alexa controlled allowing you to sit and relax while Alexa does the work. Wonderful amenities range from heated toilet seat bidets, 4 system shower panels with rain shower, a Heated Pool Add-On Option and Cabannas, 72in Fireglass Firepit, Gym Area w/TV for Streaming Workouts, Beverage Bar and more

4.91 out of 5 average rating, 302 reviews

Apartment in Gainesville

Le Chic - Near Celebration Pointe, UF, Shands

Enjoy this gorgeous gated 1 bedroom condo located near I-75 and minutes away great shops and restaurants. Whether you're in town visiting Gainesville, at the University of Florida for an event, or on a clinical rotation, this place is in a great location. Enjoy spacious living areas, Wifi, TV, a washer and dryer, a fully equipped kitchen, seated outdoor patio, and access to neighborhood amenities which includes basketball court, tennis court, and pool.