
Luxury rentals in Hillsborough County
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Top-rated luxury holiday rentals in Hillsborough County
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Luxury Beachfront House in Anna Maria!
ANNA MARIA-LOCATED JUST STEPS AWAY FROM THE BEACH AND SHOPPING! This luxury house on the bay features sweeping views of the Bay, Passage Key, Beachfront, and Skyway Bridge. With 4 bedrooms and several entertainment areas this makes an amazing retreat for a family or group of friends that have luxury tastes while enjoying the relaxed atmosphere of Anna Maria. Features include a pool and spa with a putting green and rooftop deck! This is as luxurious as it gets with a short walk to downtown shops

Tampa Luxe Waterfront Private Pool, Hot Tub & More
Welcome to the first and only Airbnb Luxe property in Tampa and St. Pete—where every detail is curated for your comfort. This professionally designed waterfront home with direct Tampa Bay access features a private pool, hot tub, dock, chef’s kitchen, fast Wi-Fi, electric scooters, Weber Grill, fishing & beach gear for your adventures & more. Perfect for families or groups seeking relaxation and adventure. Ask us about private chef services and curated local experiences to elevate your stay.

Rooftop Views! Pool, Spa and Game Room!
Love Me Blue by Exclusive Vacations VR24-000043 Welcome to Love Me Blue, part of our Exclusive Collection. This luxury beach home offers four bedrooms, four and a half baths, located on the north end of Anna Maria Island! Just a three-minute walk to the serene Bean Point beach and one mile to the shops and restaurants of Pine Avenue, this stunning home combines resort-style amenities with elegant island living. Featuring a rooftop deck, private pool with a spa, and exclusive touches like a

Onyx House at The Gemma
Just steps away from the quartz white sand of Clearwater Beach sits a brand new collection of homes, "The Gemma." With spacious layouts, modern amenities & upscale furnishings "The Gemma" vacation homes provide a haven for travelers seeking the ultimate beachfront experience. Whether you're savoring your morning coffee on a private balcony, basking by the pool, or strolling along the powder white sands of Clearwater Beach, "Onyx House" ensures that your vacation dreams become a reality.

Riverfront Oasis | Pool/Spa, Fire Pit & Games
Featured on Season 3 of the Emmy Award-winning TV series StayCation, Waterside Gardens is a meticulously crafted riverfront oasis in the heart of Tampa. “A++ this place was amazing. Best Airbnb I’ve ever stayed at. Would 100% stay here again” -Nick From the wall of windows overlooking palms and water to evenings spent watching the sunset from your own private beach, this home invites you to slow down and take in Tampa’s waterfront lifestyle. Every moment here feels extraordinary.

New-Waterslide-Spa-Rooftop-Gulf & Bay Views
Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway.

New-Endless Amenities-Unmatched Rooftop & Views
Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway.

Tripletail | Beachfront | Pool | Hot Tub
Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or rent a golf cart to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king bedroom and bathroom, open floor plan kitchen , dining and family room. Upstairs are two more King bedrooms and bathrooms as well as a sitting area. Heated pool and hot tub

Private Ultra-Luxury 10 Bedroom | 14 Bath Mansion
Welcome to THE Estate Tampa Mansion! ✦10 master ensuites ✦14 Bathrooms ✦20,000 sf of space ✦saltwater pool | HUGE hot tub ✦professional gym | Ai personal trainer ✦chef's kitchen | commercial ice machine ✦lounge/bar areas ✦art gallery ✦billiard room ✦arcade | basketball | guitar hero | racing sims | air hockey | classic games ✦20-person dining table ✦This property is not suitable for children under 10 years of age.

Rooftop+Balcony- Luxury Stay in Downtown Dunedin
These luxury townhomes were thoughtfully built as vacation havens in the heart of Downtown Dunedin, a place we proudly call home. Designed with privacy in mind, each home features professionally built lockout units between floors and neighboring townhomes, allowing guests to book individual spaces or entire homes - while always maintaining complete privacy and comfort.

Serendipity Deux: Luxury Beachfront Retreat + Elev
Luxury 4BR/4.5BA beachfront home on Anna Maria’s north end with stunning Gulf views, private pool & spa, gourmet kitchen, and elevator access. All king bedrooms feature en-suite baths. Bikes, kayak, paddleboard and Golf Cart included. (waivers, DL and Insurance required) Walk to Bean Point and Rod & Reel Pier. Perfect blend of comfort, privacy, and coastal charm.

Shangri-La | Bean Point | Rooftop Pool | Golf Cart
Escape to Shangri-La, a stunning beachfront estate on Anna Maria Island's coveted Bean Point. This private, gated sanctuary offers unparalleled Gulf views and direct beach access. Enjoy luxurious amenities, spacious rooms, and a serene atmosphere perfect for a memorable vacation. Experience the best of island living in this extraordinary retreat.
Popular amenities for Hillsborough County luxury holiday rentals
Other great luxury holiday rentals in Hillsborough County

Pearl House at The Gemma

New-Luxury Resort Pool w/ Slide&Spa-Rooftop Views

Pool, Spa & Rooftop Retreat - Direct Beach Access

New Home w/ Incredible Rooftop Deck!- Just Breathe

Beachfront Luxury - Pool, Spa & Rooftop Deck

The Gemma Collection - Four Luxury Beach Villas

Jade House at The Gemma

The Sun Deck
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- Luxury rentals Florida
- Luxury rentals United States
- Anna Maria Island
- Weeki Wachee Springs
- Raymond James Stadium
- Anna Maria Island Beach
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Reunion Resort Golf Courses - Palmer & Watson
- Bean Point Beach
- Amalie Arena
- Dunedin Beach
- Vinoy Park
- Tampa Convention Center
- LEGOLAND Florida Resort
- University of South Florida
- Hard Rock Casino
- ChampionsGate Golf Club
- John's Pass
- Island H2O Live!
- Southern Dunes Golf and Country Club
- Tropicana Field
- Fort De Soto Park
- Sand Key Beach
- Anna Maria Public Beach
- Things to do Hillsborough County
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- Food and drink Hillsborough County
- Sports activities Hillsborough County
- Tours Hillsborough County
- Nature and outdoors Hillsborough County
- Art and culture Hillsborough County
- Things to do Florida
- Wellness Florida
- Art and culture Florida
- Tours Florida
- Entertainment Florida
- Sightseeing Florida
- Food and drink Florida
- Sports activities Florida
- Nature and outdoors Florida
- Things to do United States
- Tours United States
- Food and drink United States
- Sightseeing United States
- Entertainment United States
- Sports activities United States
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