
Holiday rentals in Hillsborough County
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Top-rated holiday rentals in Hillsborough County
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Warm, inviting studio | Location! | Free Parking!
Embrace the charm of our studio apartment in Downtown Tampa, where convenience and comfort blend seamlessly. Positioned centrally to Downtown, Channelside, Hyde Park, Ybor City, and Tampa Heights, our cozy space offers a sanctuary for urban adventurers. Revel in the simplicity of our studio layout, featuring a well-appointed living area, fully equipped kitchenette, and modern amenities such as a saltwater pool, gym, and yoga studio. Discover the vibrant pulse of Tampa Bay right at your doorstep.

Pet Friendly Pool Oasis St Pete/Gulfport
Exceptionally private artist's home with a salt pool ( not heated) in a tropical landscaped fenced backyard and a large screened porch, surrounded by palm trees. 10 mns to St Pete beach , Treasure Island, Sunset beach or downtown St Petersburg. 5 mns to the old Florida downtown Gulfport and one block to pinellas trail. Our Eco and pet friendly ,(only green cleaning products and no pesticides) 1400 sqft home ( plus the 300 sqft porch) home is in a safe residential area, close to everything.

9 Mins to Downtown, Full Kitchen, KingBed, Balcony
Freshly remodeled second story apartment in a charming 1920's guest house located in trendy Seminole Heights just North of downtown Tampa with easy on/off from I-275. Features a full kitchen, living room, king bedroom, bathroom, and balcony. Walk to restaurants, hip bars, and shops, or stroll the tree-lined streets of 100+ year old houses. Minutes from all Tampa has to offer: Busch Gardens, Zoo, Downtown, Riverwalk, Hard Rock Casino, USF. Come and relax at this inclusive and welcoming space.

Cottage in the heart of Tampa close to everything
Centrally located, safe & desirable neighborhood by Hillsborough River. Corner lot, Free covered parking, easy self checkin, Bohemian style decor & vibe, stocked kitchen, SMART TVs, Laundry Rm, Fireplace. Outside Fire Pit, Picnic Table w/BBQ Grill, Hammock. Close to Lowry Park Zoo, Downtown/Convention Center, Riverwalk, Armature Works, Ybor City, Busch Gardens, Hyde Pk, Midtown, Airport, Beaches & More. Perfect for Vacation, Romantic Getaways, Family Visits, Concerts, Hockey/Football, & Work.

cute comfy & cozy 2nd Floor Guest Suite (Seashell)
Welcome to my 400sqf one bedroom second floor Mother-In-Law private guest suite. Its very cute and cozy. Once you come up the stairs, you will find a deck with outside sitting to enjoy the great Florida weather. Inside there is a full kitchen with everything you need to cook a meal and relax on the sofa and watch some streaming shows before heading to your even or wonder around ybor city or down town. My place is in a neighborhood about 1-4 miles from most of what Tampa has to offer.

Centrally Located Cozy 1-bed Private Cottage!
This adorable cottage is close to great views, art, culture, restaurants, dining, the beach, and family-friendly activities! You’ll love this private cottage because of the location, the ambiance, and the outdoor space. This cozy cottage is good for couples, solo adventurers, business travelers, and anyone needing a cozy place to stay! Parking is just steps away from the cottage with a private entrance. BBQ is available, new hot tub, and an outdoor gas fireplace for a relaxing evening!

Hyde Park "Industrial-chic" with Private Backyard
This hand-crafted, urban-industrial loft-inspired apartment was designed to offer a most unique guest experience. The home is spotlessly clean, extremely comfortable, conveniently situated, and stocked with amenities. The apartment is located just a short stroll to SoHo (2 blocks) & Hyde Park Village (4 blocks), South Tampa's premiere spots for trendy restaurants, cafes, bars, and shops, AND minutes to downtown Tampa, Amelie Arena, Raymond James Stadium, & I-275

Cozy BrickHouse Retreat •Seminole Heights• Tampa
Nestled on a quiet hill in NE Seminole Heights’ Riverbend neighborhood, this cozy retreat offers both comfort and convenience. You’ll be just minutes from I-275, Tampa International Airport, Downtown Tampa, Busch Gardens, USF, and UT—perfectly situated between the beaches of St. Pete/Clearwater and the excitement of Orlando. Inside, unwind in welcoming living spaces, rest easy in comfy beds, and enjoy all the essentials for a relaxing, stress-free stay.

Cute Place
Hello and welcome to THE CUTE place! In the center of everything fun in Tampa!! The cute little apartment as you can see on the pictures is NEWLY MADE! This place is located near many exciting parks like BuschGardens, MOSI, restaurants, USF, and MANY more places! Literally MINUTES AWAY!! From everything. Super quiet neighborhood. Come and enjoy this beautiful apartment. Private entrance and free parking space! Outside little seating for relaxing!

Tiny Tulum | Tropical Oasis in Tampa’s Heart!
Welcome to Our Romantic Tulum-Inspired Retreat! Escape to a tropical paradise at our enchanting Tulum-inspired oasis, designed with romance and relaxation in mind. Nestled in a serene neighborhood, our beautifully decorated retreat offers the perfect blend of luxury, comfort, and bohemian charm, creating an idyllic getaway for couples seeking a memorable experience. Why book a generic Airbnb when you can book a hand crafted Tropical Paradise?

Tampa Tiny Home
Experience luxury in this pristine, newly renovated home! Enjoy modern, high-end finishes in every room, with top-tier amenities for ultimate comfort. Perfectly located near the casino, fairgrounds, Busch Gardens, and Ybor City, you’ll have easy access to top attractions. Whether you’re in town for fun or relaxation, this spotless, upscale property offers the ideal retreat for your stay. Your luxurious getaway starts here

South Tampa Home • Fenced Yard • Near MacDill AFB
Modern 2-bedroom South Tampa retreat just minutes from MacDill AFB, Ballast Point Park, and Bayshore Blvd. This fully renovated home features a stylish kitchen with stainless appliances, quartz counters, fast WiFi, smart TVs, and free parking. Relax in the private fenced yard after exploring Tampa’s restaurants, waterfront parks, and nightlife. Perfect for couples, business travelers, military visits, or weekend getaways.
Popular amenities for Hillsborough County holiday rentals
Other great holiday rentals in Hillsborough County

Bayshore Beautiful Retreat

Lemon Drop

Coastal Farmhouse & Pool

Cheerful 2 Bedroom House _ French doors to Patio

Villa Tortuga: Private and Quiet Apartment

Home by Fairgrounds, Hard Rock, & Amphitheater

3BR/Central Tampa/Sexy Rooftop/Firepit/Bikes/

City Glam~Walk to Hyde Park Bayshore SoHo +Parking
Destinations to explore
- Rentals with a hot tub Hillsborough County
- Holiday home rentals Hillsborough County
- Rentals with beach access Hillsborough County
- Hotel rooms Hillsborough County
- Beachfront rentals Hillsborough County
- Guest house rentals Hillsborough County
- Rentals with a cinema Hillsborough County
- Rentals with a washing machine and dryer Hillsborough County
- Rentals with a firepit Hillsborough County
- Bed and breakfasts Hillsborough County
- Private suite rentals Hillsborough County
- Smoking-friendly rentals Hillsborough County
- Rentals with lake access Hillsborough County
- Motorhome rentals Hillsborough County
- Cottage rentals Hillsborough County
- Fitness-friendly rentals Hillsborough County
- Rentals with a fireplace Hillsborough County
- Luxury rentals Hillsborough County
- Rentals with a kayak Hillsborough County
- House rentals Hillsborough County
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- Flat rentals Hillsborough County
- Rentals with an accessible-height bed Hillsborough County
- Farm stay rentals Hillsborough County
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- Rentals with an accessible-height toilet Hillsborough County
- Rentals with an EV charger Hillsborough County
- Bungalow rentals Hillsborough County
- Pet-friendly rentals Hillsborough County
- Family-friendly rentals Hillsborough County
- Villa rentals Hillsborough County
- Rentals with a sauna Hillsborough County
- Boutique hotels Hillsborough County
- Resort rentals Hillsborough County
- Aparthotel rentals Hillsborough County
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- Tiny house rentals Hillsborough County
- Loft rentals Hillsborough County
- Serviced apartment rentals Hillsborough County
- Rentals with breakfast Hillsborough County
- Rentals with outdoor seating Hillsborough County
- Rentals with a patio Hillsborough County
- Rentals with pools Hillsborough County
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Dunedin Beach
- Cortez Beach
- Bean Point Beach
- Island H2O Live!
- Anna Maria Public Beach
- ChampionsGate Golf Club
- Southern Dunes Golf and Country Club
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Tampa Convention Center
- Things to do Hillsborough County
- Art and culture Hillsborough County
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- Food and drink Hillsborough County
- Nature and outdoors Hillsborough County
- Tours Hillsborough County
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