Holiday rentals in Hillsborough County

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Top-rated holiday rentals in Hillsborough County

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

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Guest favourite

Home

4.89 out of 5 average rating, 9 reviews

Brand new home, Modern design, Close to Beaches

Conveniently located only a 10-minute drive from the Indian Rock beaches, 18” To Clearwater Beach,our rental provides, Experience coastal comfort at its finest with our thoughtfully designed rental, featuring openness modern amenities and a relaxing atmosphere for your beach getaway with 3 bedrooms 2 bathrooms 7 beds sleeps 10 , brand new modern designed home. Explore the vibrant beach town just moments away, filled with charming shops, delectable dining options, and lively entertainment venues

Superhost

Villa

4.88 out of 5 average rating, 88 reviews

Paradise Luxury Resort Lakefront Pool spa Villa

LUXURY Lakefront Mansion on absolutely amazing Resort Style Estate on over 2 acres. something for everyone. Lay out by the pool, relax in the spa or shoot pool in the game room. Watch the sunrise/sunset on the dock. Or go tubing or wake boarding on the lake. It's breathtaking! Relax in the hot tub or roast marshmallows on the fire pit after a long day at the beach, area amusement parks or golf. *parties and events are not permitted Front & Back Patio, and drive, are monitored by cameras

Guest favourite

Home

5 out of 5 average rating, 52 reviews

Coastal Getaway~Spacious~ 5 min to Madeira Beach!

Relax at our spacious, elegant, coastal getaway home and enjoy its proximity to the Top 25 Beaches in the US. Madeira Beach (2.3 miles), voted #9 and St. Pete Beach voted #1 (7.7 mi ) in 2021. Modern kitchen provides abundant space for meals and entertainment. Dine out or Door dash, we are centrally located near restaurants and shoppings area. FL Botanical Garden 5mi, Pinellas Bike Trail 1 mi. Walsingham, Lake Seminole, and Veterans Memorial parks all within 4 miles.

Guest favourite

Guest house

4.97 out of 5 average rating, 105 reviews

Cozy 2 Bedroom - 12 Minutes from Clearwater Beach

Make your vacation relaxing, fun and easy! - Kick back in the hammock or have some coffee with loved ones in the peaceful private backyard. - Take the 12 minute drive to the beach with the provided boogie boards, chairs and sand toys. - Take a walk or bike ride on the gorgeous Pinellas Trail. You'll also find some of the best coffee, food and ice cream on the way. -Golf courses close by. This is a separate unit that shares a driveway and parking area with the front house.

Guest favourite

Apartment

4.88 out of 5 average rating, 164 reviews

Awesome Madeira Beach Location Close To It all!!!

JUST ACROSS THE STREET FROM THE BEACH!!! Enjoy a great vacation stay in Madeira Beach! This is a 1 bedroom 1 bath condo, one floor, easily accessible unit. (One Queen Bed in bedroom, One pull out couch, one Queen murphy bed in living room). I have provided Beach Toys, Beach Cart, Coolers, Chairs Close to Beach Acess, Intercoastal Access, and lots of Restaurants and Bars. Johns Pass is less than a mile away. Madeira Beach is South of Clearwater and North of St Pete Beach

Superhost

Townhouse

4.84 out of 5 average rating, 44 reviews

St Pete Beach @ Treasure Island #1 Beach in US 2BR

Voted 2024s #1 Beach in the USA!! Location location location. 3 minute walk to IntraCoastal waterway and 7 minute walk to Gulf of Mexico beaches (3minutes by bike.....provided). This 2BR 1BA condo is completely renovated and ready for your vacation getaway. Unique corner end unit has its own private patio. Rental also includes use of pool, 2 bicycles, 2 kayaks and tennis supplies (court right across street) and more. Short term rental permitted (3 night minimum).

Guest favourite

Townhouse

4.91 out of 5 average rating, 120 reviews

Ruskin Retreat

Our townhome is located in the beautiful Carribean style resort of Little Harbor. Resort amenities for you to enjoy are the large swimming pool and hot tub, basketball court, playground, private kayak launch, private beach (beach chairs and umbrella small fee), water toys for rent. Sunset Bar and Grill adjacent to beach and Hooks by pool , all within walking distance. Disney an hour and a half away and Tampa International Airport only 45 mins.

Guest favourite

Flat

4.8 out of 5 average rating, 293 reviews

Fiesta Siesta: Bright+ Cozy+ Unforgettable (4plex)

🌵Fiesta Siesta – Where Every Day Feels Like a Party!🌴 Feed me tacos and tell me I’m pretty—because life’s too short for anything less! Welcome to Fiesta Siesta, a fun, vibrant escape just steps from Upham Beach in sunny St. Pete Beach. One of four uniquely themed units in a gated complex, this playful retreat is decked out in a vibey cactus theme that’s all about fiesta and siesta—because, why choose? Book now and let the fiesta begin! 🎉🌮

Superhost

Home

4.8 out of 5 average rating, 61 reviews

Beautiful Retreat Haven/ 7 miles to beach

Indulge in the perfect vacation getaway with our splendid 3-bedroom, 2-bathroom listing. This beautifully renovated property offers the allure of an outdoor fire pit, a recent brand new remodel, and the convenience of WiFi and smart TVs throughout the entire house. Nestled in a tranquil and quiet neighborhood, we're just 7 miles away from the sun-kissed beach, offering you the best of both worlds - peaceful relaxation and coastal adventure.

Guest favourite

Flat

4.98 out of 5 average rating, 233 reviews

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

Guest favourite

Home

4.93 out of 5 average rating, 43 reviews

Private pool, Golf Cart, Completely Renovated!

Discover the ultimate retreat in a central location! Golf cart to Down town, restaurants, breweries, parks, and trails! Multiple beaches with-in a 10 minute drive. This thoughtfully equipped home is an oasis of leisure, offering a pool, games, and a fully-equipped kitchen. Optional Golf cart rentals, private boat rides and fishing trips add to the excitement. Book now for an unforgettable experience!