
Resort vacation rentals in Hillsborough County
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Top-rated resort rentals in Hillsborough County
Guests agree: these resort rentals are highly rated for location, cleanliness, and more.

Little Harbor Hideaway
Welcome to Little Harbor Hideaway! Enjoy the Beach, 2 pools,Hot Tub & Kayaking on Cabbage Creek. We also have 2 restaurants on property. * New PickleBall courts & CornHole boards Our Unit has a very nice king bed as well as a sectional couch with pull out full bed. This unit has a full refrigerator and also has a built in flat top electric stove. 50in Sony Smart TV for Netflix etc +cable New A/C in late 2023 This is a 2nd FL unit w/ large Balcony new Washer & Dryer in common area near steps.

2-bdm dlx CONDO Wydm,2-bath, full kitchen,8-guests
Club Wyndham Clearwater Resorts offers white sand beachfront getaway. This 2 bdrm deluxe, 2 baths, full kitchen. This resort offers a stunning view of Florida’s coast. Amazing Beautiful Sunsets, while relaxing at this resort’s airy accommodations, designed with tranquility in mind. Stroll the boardwalk at Pier 60 and watch for dolphins aboard a catamaran or schooner tour. Embrace the city’s casual vibe and ocean breezes while enjoying a vacation that follows your pace. Spacious condo sleeps 8.

Little Harbor Hideout
Welcome to Little Harbor Hideout! Enjoy the beach, 2 heated pools, Hot Tub or Kayaking on Cabbage Creek. We also have 2 great restaurants on property so no need to get in the car. *New Pickleball courts & Cornhole Our unit has a New King Bed, a couch, full size refrigerator so no bending down to some tiny refrigerator. 50in Sony Smart TV w/cable + New A/C in Jan. 2025 This is a 2nd FL unit w/large Balcony. New Washer & dryer in common area New Game room for kids w/air hockey etc

Beachfront Traditional
Located in the Shells building. Enjoy breathtaking sunset views from your large picture window which overlooks Treasure Island’s wide sandy beaches along the Gulf of Mexico. This 297 Sq. Ft. beachfront guest room features (2) Queen Pillow Top Beds. Other features include: * 55” LCD Flat Panel TV * Mini Refrigerator * Microwave * Coffee Maker * Toaster * AM/FM Clock Radio * Hairdryer * Iron, Ironing Board * Electronic Safe * Ceiling Fan * Beach Towels

Adorable Affordable Beach Efficiency
A Beach Adventure Awaits You..Come Play Or Relax @ the Coral Resort Clearwater Beach, Fl This small , lovely island is all water, beaches, restaurants and fun. NO CAR NEEDED. Bike or walk the beach. Visit: Winter the dolphin is right here... White sand will surround you on all these public beaches . Free parking/ internet. Managers onsite. 24 hr Fishing Pier on site. Rent jetski/boats in walking distance. YOLO Note: Unit A5 is a second floor/no elevator.

Treasure Island Beachfront Resort with pool
Amazing beach views from your vacation condo unit and from your private balcony. Newly refreshed privately owned condo at the Island Inn Beach Resort in Treasure Island Florida. Treasure Island is next to St. Pete Beach, south of John's Pass, Madeira Beach, Indian Rocks and Clearwater beaches. Pool bar, heated pool on beach, kitchen with two burner hot plate, pots, pans, coffee maker, microwave and more.

Suite 2
2 - 6 Guests Beds : RM 1- King, RM 2 - Full, Twin/Twin Bunk Marble Tub and Shower Combination Fully Stocked Efficiency Kitchenette Keurig K-Cup, Refrigerator, Micro/Conv Oven Toaster, Complimentary Coffee/Condiments Hair Dryer, Complimentary Toiletries Beach Towels, Spa Robes 2-TV’s, Secure WIFI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades

Suite 5
2 Guests - Bed : Queen Dining Bar and Leather Seating Area Marble Bathroom and Shower Fully Stocked Efficiency Kitchenette Keurig K-Cup, Refrigerator, Micro/Conv Oven Toaster, Complimentary Coffee/Condiments Hair Dryer, Complimentary Toiletries Beach Towels, Spa Robes 1-TV, Secure WIFI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades

Suite 1 - Rod and Reel Resort
2 Guests - Queen Bed; Marble European Oversized Shower, Dual Wardrobe and Built-in TV, Keurig Coffee Maker, Hairdryer, Outdoor Refrigerator for Drinks, Complimentary Toiletries, Complimentary Coffee and Condiments, Beach Towels, Spa Robes Secure WI-FI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades, and Complimentary Bicycles.

Clearwater Beach Collection King Bed 6th Floor B
Relax in comfort in this Mediterranean styled guestroom. During down time enjoy your favorite programs on a flat screen HDTV, or stay connected with friends and family with complimentary wireless internet access. Other amenities important for a comfortable stay include a coffee maker, hair dryer, iron and ironing board.

Clearwater Beach Resort - 1 Bedroom Deluxe
Oceanfront Pool & Private Beach Access – Clearwater Beach Escape – Clearwater Beach, FL Start your day with a sunrise walk along the beach, enjoy a refreshing dip in the pool, savor local seafood at nearby restaurants, and end your evening with breathtaking sunset views from your suite.

Tradewinds - Studio Boulevard View
Oceanfront Paradise & 8 Heated Pools at Bluegreen at TradeWinds – St. Pete Beach Wake to Gulf breezes, dip into one of eight heated pools, stroll the white-sand beach, sip cocktails at the tiki bar, then watch the sunset over the waves from your balcony.
Popular amenities for Hillsborough County resort rentals
Family-friendly resort rentals

Tradewinds - Studio Boulevard View

Tradewinds - Gulf Front Studio

Tradewinds - Gulf Front Studio

Tradewinds - Standard Studio Boulevard View

Tradewinds - Gulf Front Studio

Tradewinds - Gulf Front Studio

Tradewinds - Gulf Front Studio

Tradewinds - Studio Boulevard View
Resort rentals with a pool

Tradewinds - Gulf Front Studio

Tradewinds - Gulf Front Studio

Tradewinds - Gulf Front Studio

Tradewinds - Gulf Front Studio

Tradewinds - Studio Boulevard View

Tradewinds - Gulf Front Studio

Tradewinds - Studio Boulevard View

Tradewinds - Gulf Front Studio
Resort rentals with a gym

Tradewinds - Studio Boulevard View

Tradewinds - Studio Boulevard View

Tradewinds - Studio Boulevard View

Tradewinds - Studio Boulevard View

Tradewinds - Studio Boulevard View

Tradewinds - Studio Boulevard View

Tradewinds - Studio Boulevard View

Tradewinds - Studio Boulevard View
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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
- Dunedin Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- 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
- Bok Tower Gardens
- Gulfport Beach Recreation Area
- Adventure Island
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