Holiday rentals in Dade City

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Top-rated holiday rentals in Dade City

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

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Top guest favourite
Farm stay in Dade City
4.94 out of 5 average rating, 382 reviews

Florida Breeze - 18 Acre Wildlife Sanctuary

Have you ever wanted the opportunity to feed an egg to a fox? Or feed a grape to a lemur? Hand feed a deer or sheep? Dance with a cockatoo? If so you’ll get to have these and many more experiences here during your stay. Our Airbnb is different, and our main focus is on offering rememberal experiences to our guests. We have a small family run 501C-3 wildlife rescue here on our 18 acre facility that you will be staying at. We do live on the property, but in a detached house across the driveway.

Top guest favourite
A modern living area features a plush navy blue couch and loveseat arranged around a glass coffee table. A large television is mounted on a white media console. Soft gray curtains frame a bright window, while a light area rug adds warmth to the space.
Flat in Dade City
4.95 out of 5 average rating, 124 reviews

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.

Top guest favourite
Plane in Brooksville
4.98 out of 5 average rating, 149 reviews

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!

Top guest favourite
An outdoor porch features a two-person Jacuzzi, inviting relaxation while overlooking a lake. Warm lighting is provided by lanterns, creating an ambient atmosphere against the backdrop of a colorful sunset and silhouettes of trees.
Tiny home in Dade City
4.98 out of 5 average rating, 215 reviews

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Experience the perfect blend of an eco-friendly retreat and modern luxury of our lakefront container home. Nestled in the heart of nature, this stylish oasis promises an unforgettable experience where you can immerse yourself amidst the beauty of the countryside without sacrificing comfort. Plus, enjoy the opportunity to interact with our farm animals, adding a touch of rural charm to your agritourism escape. Also, feel free to check out my other listing, Casa de Elvira on my host profile.

Top guest favourite
A cozy seating area is highlighted by a warm-toned leather sofa. A unique wooden table with blue accents adds character, while large windows allow natural light to brighten the space. The loft area can be seen above, with greenery peeking in from the surroundings.
Campsite in Thonotosassa
4.99 out of 5 average rating, 314 reviews

The Palm Tree Getaway

Ever stayed the night in the woods? Cross it off the bucket list with our ‘tiny-house’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 1G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

Top guest favourite
Farm stay in Dade City
5 out of 5 average rating, 44 reviews

Luxury rural-farm stay-pool-farm animals-private

The Guesthouse at 3 Ponds Farm is located in Central Florida on a 22 acre family farm, at the end of a gravel country road. The house is private and secluded, situated under majestic oaks dripping in Spanish moss, and is convenient to both popular amusement parks and Florida's beautiful natural springs and wildlife. Enjoy the pool (not heated) fire pit & yard games The Guesthouse is perfect for a family vacation, girls getaway, fishing trip, or to celebrate a romantic anniversary.

Top guest favourite
The exterior of the home showcases a spacious front porch with a charming swing surrounded by greenery. The light-colored walls and dark roof contrast with the extensive lawn, while large windows provide views into the inviting interior. A decorative star and hanging plants enhance the porch's welcoming appearance.
Home in Webster
4.89 out of 5 average rating, 100 reviews

Quet’s Place | 10-Acre Retreat in Richloam

Escape to the peace and quiet of Old Florida at Quet’s Place, a private 10-acre retreat tucked down a scenic gravel road in historic Richloam. Relax on the front porch with your morning coffee, watch wild turkeys and deer pass by, and unwind in a setting that feels a world away from the noise. Whether you're looking to slow down and enjoy the country or explore nearby attractions, this is the perfect place to relax and recharge.Just about an hour from Florida’s major theme parks.

Top guest favourite
Flat in Dade City
5 out of 5 average rating, 8 reviews

The Carriage House

The Carriage House – Downtown Dade City The Carriage House is a spacious 2,000 sq ft private two-story residence in the heart of Downtown Dade City. Featuring two bedrooms, two full baths, a king master suite, office space, full-size washer and dryer, dining area, and private entrance, this beautifully appointed home offers comfort and convenience just steps from shops, dining, and local charm. Ideal for extended stays, business travel, or a relaxing downtown getaway.

Top guest favourite
Home in Dade City
5 out of 5 average rating, 22 reviews

Peaceful Home Retreat w/Pool Near St. Leo

Comfortable 2BR/1BA single-family home in a residential neighborhood, ideal for visiting family, extended stays, remote work, or local events. Includes a dedicated workspace and internet service (best effort; speeds not guaranteed). Enjoy a large screened-in lanai with an outdoor kitchen and a private yard with a gated in-ground pool (seasonally close November through February; No Heater). Owners live nearby and are available if needed while respecting guest privacy.

Top guest favourite
A spacious living area features a comfortable sectional sofa adorned with decorative pillows. A coffee table sits in front, with a tray positioned on top. The kitchen in the background includes a black refrigerator and a dining table surrounded by chairs, illuminated by pendant lighting.
Guest house in Zephyrhills
4.99 out of 5 average rating, 108 reviews

Under The Oaks Cottage

A charming cottage nestled beneath majestic oak trees, combining country living within reach of city amenities. This comfortable space features one bedroom with a king size bed along with built in bunk beds in the main living area. Savor a morning cup of coffee in the screened back porch while enjoying the beautiful tropical foliage. Chickens, goats, cows, and a horse forage nearby. You could possibly be entertained by the goats playing on the roof-tops.

Top guest favourite
An aerial view captures a rustic property surrounded by lush greenery, including oak and hickory trees. A winding path leads from the road to the guest house, which is nestled within the expansive landscape. A serene lake is visible in the background.
Guest house in Dade City
4.95 out of 5 average rating, 230 reviews

Hickory Breeze Guest House

We invite you to come and enjoy our little piece of country in north Pasco County, Florida! Not fancy, but comfortable is our objective for our guests! We are not a business (nor are we owned by a business) therefore we do not conduct our hospitality like a business, but rather as hosts looking to meet and make new friends! We do all our own cleaning and set-up in the guesthouse so that we know it is done the way we would do it for our own family.

Top guest favourite
A modern kitchen and living area create a welcoming open space. The kitchen island, adorned with neutral decor, features a double sink and modern appliances. Natural light floods in from the windows, illuminating the comfortable seating area with a cozy sofa and stylish accent lamp.
Tiny home in Zephyrhills
4.99 out of 5 average rating, 263 reviews

💙Tiny House New Build Near Park, Pond & Downtown

Experience a 2020 Tiny House on Foundation • One of three tiny houses on lot! • 360 SF / 1 Level • Weekly & Monthly Discounts • Private Front Porch • Steps to Beautiful Zephyr Park • 6 min. walk to Historic Downtown Main Street • Stocked + Equipped Kitchen • Charming Residential Neighborhood • Built by specialized FL Tiny Home Builder • Washer/Dryer • FiOS Wifi 500 Mbps • Onsite Private Parking • New sidewalk from parking pad to front steps

Popular amenities for Dade City holiday rentals

When is the best time to visit Dade City?

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Frequently Asked Questions

  • Where should I stay in Dade City?

    Make yourself at home in Dade City by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Orange Park, over 30 vacation rentals in Madill, and over 70 vacation rentals in Claireview.

  • Are there vacation rentals with a dedicated workspace in Dade City?

    Yes! Work meets play with ease at over 20 vacation rentals in Dade City featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Dade City?

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

  • How much does it cost to stay in house rentals in Dade City?

    Experience the best of Dade City with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Dade City vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Dade City, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Dade City have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Dade City. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Dade City

  • Total holiday rentals

    Explore 30 holiday rentals in Dade City

  • Nightly prices starting at

    Dade City holiday rentals start at £44 per night before taxes and fees

  • Verified guest reviews

    Over 1,570 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Dade City holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Dade City rentals

  • 4.8 Average rating

    Dade City stays are highly rated by guests – averaging 4.8 out of 5!

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  2. United States
  3. Florida
  4. Pasco County
  5. Dade City