
Holiday home rentals in Hillsborough County
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Top-rated holiday home rentals in Hillsborough County
Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

FREE Decor AnyOccasion*Romantic Getaway*Relax Bath
A modern & cozy place in Tampa,private entrance and parking.We include decorations for all occasions:birthday,wedding,special day, show your love, and more!Perfect romantic getaway to enjoy with your loved one.Located in a central area of Tampa,close to Bush Garden/Adventure Island,Raymond James Stadium,Tampa International Airport, Ybor City, Downtown Tampa,Amalie Arena,River Walk,Clearwater/St Pete Beach and more! Peaceful and centrally-located place with very good restaurants and many shops.

#17 New Executive King Bed Home - Joyful Moment
Leave the stress of everyday life behind and head to this 2-bedroom, 2-bathroom home in Tampa. This well-appointed vacation rental has enough room for your group and is conveniently located near plenty of family-friendly activities. At this home, you’ll also be far enough from downtown that you can relax, but close enough to take advantage of all of the professional sports games, museums, and parks that the city offers. After a day out enjoy the backyard and the Beautiful Lake. pictures to come

Modern Home Great Location
Welcome to your home away from home. Our guests’ comfort is our priority. Equipped with all your creature comforts and surrounded by modern fixtures and decor to ensure a wonderful vacation. Open Floor plan, huge kitchen, and two cozy bedrooms. Walking distance to all the local restaurants and attractions, without the noise to keep you up at night; you couldn't choose a better location Please note: this is a duplex property, so you'll be sharing the building but enjoying your own private space.

Sun & Salt Air House-3BR home w/patio,pool,firepit
The search for the perfect sunset with friends and family is over. Minutes from one of a kind shopping, diverse dining, horse racing, and hiking. There is something for everyone. Home is completely renovated with gorgeous stone floors, chef kitchen, and custom outdoor space. Watch the Game on the 75" TV, or relax on the oversized patio/pool area. Enjoy the picturesque sunset before taking an evening dip in the LED lit salt water pool while staying warm by the gas firepit with loved ones.

Villa Al Golfo Tre Pristine Waterfront Oasis
Pristine villa in the lovely seaside gulf town of Indian Rocks Beach, 2 short blocks to the beach with intracoastal waters in the backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio and your own show stopping indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam beds & security safe.

Davis Island Spanish gem
Quiet Davis Island luxury living, close to everything you want in Tampa but feel like you escaped from it all. Davis Island is the premier neighborhood in Tampa for this very reason, an island of beautiful homes and walkable neighborhoods! Easily walk to all dining on Davis Island, or a 3 minute Uber to Channelside and Sparkman Wharf. The property is fully equipped home with everything you need for an extended relaxing Tampa visit, or stay a few days and avoid the noise of downtown.

Stunning Waterfront Condo at Boca Ciega Resort 310
Do you want to watch dolphins from your balcony? Our condo is beautiful right on the water with a boho style interior design. Large balcony with stunning view over Boca Ciega Bay. Dolphins come in every evening. 4 people easily sleep here, two in the King size bed in the bedroom, and 2 in the $1,600.00 queen size sofa bed in the living room. Fully equipped bar kitchen. There are 2 TVs, Wi-Fi, and washing machine with dryer. Private parking. The condo is smoke free and pet friendly!

Serene Waterfront Townhome at Little Harbor
Come enjoy yourself at our townhome. Relax with the whole family at this peaceful place to stay with four private balconies. Our townhome is located in the seaside village of Little Harbor with a white sand secluded beach, two waterfront restaurants, seaside pool, tennis courts, fishing piers, watersports rentals, two onsite marinas, and much more. Enjoy watching the fish jump and the many varieties of birds in the natural preserve framed by the canal from your private balconies.

Bright & Breezy Tropical Home Minutes to Beach
Relax & Recharge in a Stylish Mid-Century Tropical Getaway – Just Minutes from the Beach! 2BR/2BA with a bonus bedroom in the Florida room—sleeps up to 8. Nestled in a quiet neighborhood just minutes from Indian Rocks and Clearwater Beach, plus great dining and shopping. Enjoy a private fenced backyard and BBQ area. Perfect for families or groups seeking comfort and convenience. Pet-Friendly! One well-behaved dog is welcome (additional $225 pet fee applies). Sorry, no cats.

4-bedroom Vacation home with heated pool family
🎊🎉🎊🎉A new surprise for you, the house has been completely renovated .2025 🎉🎊🎉🎊Bring the whole family to this great place with lots of room for fun. Fishing lake. Free one bottles of wine. **Near Amenities:*** Our location is very convenient, just a short distance from key tourist attractions and local shops. You can easily explore local culture and enjoy new experiences. Contact us to book now and experience our comfortable and warm space!

Maximalist space w/eclectic style/Bars close by
Welcome to my little slice of paradise! This sunny 2-bedroom retreat sits on the top floor of a charming Floridian townhouse, right in the heart of trendy Seminole Heights. Just a short stroll or bike ride to buzzing cafes, cool bars, local breweries, and foodie hotspots—Tampa’s tastiest treasures are all around you! Whether you're here with family or friends, you're in for a fun-filled stay packed with flavor, flair, and good vibes.

*Updated House* 3 minutes to Beach Access
Welcome to our Bay Haven Breeze where you can bask in the beautiful Gulf Coast when you and up to 6 family and friends vacation at Indian Shores/Indian Rocks Beach, Florida. This house is newly renovated that offers upgraded modern amenities. Within 3 minutes drive from your doorstep, you can be dodging gentle waves and wiggling your toes in silky sugar-white Gulf sands.
Popular amenities for holiday home rentals in Hillsborough County
Family-friendly holiday home rentals

Renovated 2 bed/1 bath North End, beach 2 min walk

Modern Home Great Location

Maximalist space w/eclectic style/Bars close by

Beautiful Clearwater home!

Stunning Waterfront Condo at Boca Ciega Resort 310

Sun & Salt Air House-3BR home w/patio,pool,firepit

Davis Island Spanish gem

Villa Al Golfo Tre Pristine Waterfront Oasis
Holiday home rentals with a patio

Lovely one bedroom, Private Bungalow

Waterfront Escape: 5Bed, 3Bath, Heated Pool!

Beach Condo - Ram Sea - 3BR Condo right on Beach

GK Oasis 2 King BR Dock Kayaks Canal Pool Spa ;Pet

Modern 4 BR Heated Pool House w Theater Game Room

Sunrise Escape waterfront - pool heater avail

Beach House BTR#2042

Lovely Efficiency with Patio near Beach
Holiday home rentals with a washing machine and dryer

Central Florida Vacation Stilt Home with pool!

Lovely 1 bedroom, unique outdoor space, near park

Waterfront Seaside Oasis! Dog-Friendly, pool & spa

Mango Tango Cottage. Renovated September2025

Luxury Modern Waterfront Home with Private Dock

Contemporary 2 KING Bedroom newly remolded central

Brand new vacation rental one block from the beach

Centric Vacation Home with Tiny House near Beaches
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- Anna Maria Island
- Busch Gardens Tampa Bay
- Raymond James Stadium
- John's Pass
- Reunion Resort Golf Courses - Palmer & Watson
- Dunedin Beach
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Cortez Beach
- Amalie Arena
- Anna Maria Public Beach
- Island H2O Live!
- Bean Point Beach
- Jannus Live
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
- Bok Tower Gardens
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