Pet-friendly vacation rentals in Sumter County

Dade City Restful Retro Retreat

You will be close to everything when you stay at this centrally-located home. Thirty minutes from Tampa and Wesley Chapel, one hour to Disney and minutes to numerous wedding venues and amenities in the Dade City area. Come and enjoy the quaint downtown of Dade City, while still being close to all the action. The apartment has TVs and cable, in each bedroom and living room, kitchen with all amenities, washer and dryer and garage. We ask for dogs to be under 30lbs for reservations over 30 days.

Serendipity Lake private dock, canoes & kayaks

What a view, what a really good view, YES IT IS! Watch the sunrise and sunset over the water on a private dock. We have 2 canoes and 2 kayaks to enjoy the water or bring your boat! This is a place you will want to come back to time and time again. Water views from all angles, you will feel like you're on a houseboat there's so much water! Plenty of room for outdoor games and activities. Pet friendly. Just a short drive to downtown Inverness and 30 minutes to Crystal River. Simply perfect!

Peaceful Cottage Mini Farm/Garden Near Villages

Perfect Getaway! Enjoy our clean, peaceful, chic tiny farmhouse located on our 1.5 acre homestead. This is the perfect location as we are 5 minutes from I75 and Florida Turnpike. We are 10 minutes from LIVE Music, Restaurants and more in the Brownwood Town Square. We offer free parking for 2 vehicles and welcome well behaved dogs. (Please let me know if you are bringing your furry friend) Looking forward to hosting you! 1 h. from Orlando/Disney & Tampa/Busch Gardens 25 m. Leesburg Hospital

Private 2/2 Villa w/ New 4 Seat Gas Golf Cart

Relaxing home in quiet neighborhood w/ private yard, screened porch - rare in The Villages! Roanoke Retreat is a beautifully remodeled 2 bed/2 bath home - only 15 minute golf cart ride to Spanish Springs, 20 minutes to Sumter Landing . Rental includes 4 seat gas golf cart w/ access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in every room, fully equipped kitchen, new BBQ grill. 55+ community but no age restriction to visit

Inverness Home with a View

Relax in a clean, welcoming, home that has been updated. There are 2 fishing poles available for your use. We make sure they are in working condition and well maintained. Shopping, restaurants, and entertainment is close by. Want a beach....35 minute ride to Fort Island Trail Beach and boat ramp. We do allow hypoallergenic small dogs (2 max), non-shedding, 25 lbs. or less, each w/ proof of shot records, please bring a kennel with you. There is a non refundable $25.00 per dog fee.

The Cove Point House

Escape to this beautiful retreat surrounded by picturesque ferns on beautiful Lake Henderson. Relax on a screened in porch in one of the most utilized rentals around! Our piece of paradise offers a private dock with stunning views of the sunset and scenic native plants. Lounge on the back deck and grill your favorite meal. Be wonderstruck by personalized touches, customized light fixtures and knotty pine ceilings. Bring the family as the second bedroom offers two twin sized beds!

New home in the new part of the villages.

Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

Chic 3/2 Home in The Village of Citrus Grove

Welcome to your perfect getaway in The Villages, Florida! This beautifully designed 3-bedroom, 2-bathroom home offers a blend of modern elegance and cozy charm, creating the ideal space for relaxation and entertainment. Just 1 mile from Sawgrass Grove Market and 7 miles from Brownwood Square, you’ll be close to live entertainment, dining, pools, pickleball, and golf—endless fun awaits!

Country getaway

You won’t forget the peaceful surroundings of this rustic destination. Former inn-keeper offering this unique space on Wildfire's Ranch. Centrally located from Ocala, Tampa and Orlando. Short drive to the Villages. Set in the country but minutes from shopping and restaurants. Secured gated entry and easy access to interstate 75. If you like the holidays you will love it here.