Vacation rentals with breakfast in Sumter County

A Little Bit of Heaven

Come enjoy life in Florida’s friendly town: The Villages!Beautiful, updated, contemporary “beachy”decor! Quiet, friendly upscale neighborhood; 3mi. to Spanish Springs or Sumter. Backs up to the beautiful entrance to Glenview; Has ponds /waterfalls/wildlife! Relaxing!! Private entrance /Parking 1-BR, 1-B, 1-living space/kitchenette, back patio/yard. Laundry. WI-FI. Rent:$80-97day, depending on the time of year. (Min. 5 night) clean $100.+ Dam. dep. +7% tax ALREADY BOOKED Dec.1,2024-Ap.1, 2025

Location · View · Accuracy

Living the Dream | Pools, Golf & Entertainment

Beautifully furnished 3-bedroom home in The Villages, just 5 minutes to Sumter Landing. Surrounded by walkable championship and executive golf courses. Golf cart included for easy access to dining, shopping, and nightly entertainment. Enjoy new furniture, a heated massage recliner, enclosed lanai, private landscaped backyard, and a peaceful neighborhood—perfect for relaxing or enjoying the active Villages lifestyle. Book now and experience The Villages the way it was meant to be enjoyed!

Location · Family · Bathroom

Villages Perfect Location•Priv Suite•Walk to Pool

• 🔐 Private entrance& bedroom, full bath and while staying in a beautifully maintained shared home in The Villages ❤️ Gorgeous Interior * GUEST Passes MM Free 🏊‍♂️ Heated adult POOL/3 min walk 🛏 New Sealy Q Bed, WiFi, RokuTV ( Prime, Peacock), Workstation,Sound Machine, yoga mats ☕️ Coffee Bar & Teas 🍴Kitchen shared *Living Room not shared 🧺 W/D * Outside security camera/Ring/ front door * 🚭 No smoking, vaping, e-cigarettes, chewing tobacco/illegal drugs anywhere on property

Family · Location · Sleep quality

Historic Sweetwater Cottage |Fenced Yard & Firepit

Stay in a charming pet friendly 1920s historic home in Dade City featuring a fully fenced yard, front porch swing, and firepit.— thoughtfully updated with modern comfort. Highlights: • 2 bedrooms: 1 king bed, 1 queen bed + air mattress • Front porch swing — perfect for morning coffee or evening relaxation • Deck with grill for outdoor dining • Firepit with chairs for cozy nights • Cornhole game for added fun • Just 10 minutes from downtown Dade City • 15 minutes from Saint Leo University

Value · Family · Long stay

Charming Lakefront Retreat with Private Dock

Our lakeside retreat is situated in Lake Panasoffkee, a charming rural community that offers stunning vistas of the lake. The area boasts a rustic ambiance, making it a truly picturesque getaway. From fishing spots, private dock, kayaks & paddle boat, jacuzzi with the most amazing view of the lake, BBQ area, fire pit right on front of the lake, plenty of porches to enjoy all the beautiful views of the lake & canal, even when you are making those delicious meals.

Family · Location · Quiet

Farmhouse Stay / Perfect for Florida Adventures

Escape to the peace and quiet of Old Florida at this private 10-acre farmhouse retreat. Sip your morning coffee on the porch, watch wild turkeys and deer wander by, and enjoy a slower pace surrounded by country. Tucked down a scenic gravel road in historic Richloam, it’s a peaceful home base for exploring Central Florida. **Perfect for snowbirds and extended winter stays** looking for a quiet Florida getaway, with major theme parks about an hour away.

Family · Value · Sleep quality

Villages Clean, Comfortable Room & Private Bath

Fiona & I bought our new home in The Villages, Sept 2020. We were successful Airbnb hosts in our prior home since 2017. We are "young" retirees after long careers in aerospace & health care. We absolutely LOVE being hosts & meeting different people. During your stay we will make you very comfortable. We offer complimentary breakfast; tea, coffee, toast, cereal, milk etc. We can get you a guest ID if you plan on using the amenities.

Location · Value · Amenities

Latitude 28 a little Patch of Paradise!

"Latitude 28" in Floral City is a spacious 2 BR/2BA Mobile Home. Book now for full 6 month special rate Oct thru March! Semi-open living, split bedrooms; Cozy Queen in primary & ensuite bath. Guest features Full bed. Amenities include 40" Smart TV, Wi-Fi, fully equipped eat-in Kitchen w/Keurig. Large Sun Room overlooking the expansive lawn great for Birdwatching and located just .07 miles from Trail for Cycling Enthusiasts!

Family · Value · Hospitality

New Home/ 3/3/Heated Pool/2 Golf Carts/Golf course

Luxury new-construction 3BR/3BA home on a championship golf course, professionally decorated with upscale finishes throughout. Enjoy a private heated pool, stunning east-facing sunrise views, and a fully stocked gourmet kitchen. Includes premium linens, plush towels, front-load washer/dryer, and 2 golf carts for a quick 3-minute ride to downtown Eastport. Designed for comfort, style, and an unforgettable golf getaway.

Fancy Floridian $175 per night Special - 2 nights

Fun Airbnb to spend time with loved ones. Multiple bedrooms with 4 queen beds - perfect for a large family gathering or ladies only time away. One gorgeous bathroom with roll in shower, brand new washer and dryer, half bath in adorable pirate theme, hand painted under the sea walls, beach scenes, lovely adult Mermaid themed bedroom, lots of exciting decor and lots of activities to do!

Family · Hospitality · Comfort

Vibrant Villa-Sumter Landing! NEW Golf Cart, KING

This 2BR/2BA Villa puts the BEST of The Villages at your fingertips! Step outside to your own private putting green & patio. Inside, an open floor plan & lanai invite you to relax. Your Adventure begins with a NEW 4 seat Golf Cart & Townie Bikes. Prime Location, In-between Sumter Landing & Spanish Springs. 5 min to Pools, Golf, Pickleball & Town Square Entertainment!

Family · Location · Getting around

Tropical Oasis!

My Tropical Oasis is Stunning! After an active day in The Villages, cuddle up in the corner of the lanai sectional with a glass of wine. Ask Alexa to play soft music. Turn on the fountain, and landscape lighting and allow your mind to whisk you away to a tropical island.

Family · Location · Comfort