Villa holiday rentals in Pinellas County

IRB Harbor House Semiprivate Waterfront Pool Villa

IRB Harbor House, your coastal getaway nestled in the heart of Indian Rocks Beach. This unique shared property concept with semi-private villa boasts 2 cozy bedrooms, 2 modern bathrooms & full size kitchen; perfect for small families, small groups & professionals. Enjoy the convenience of upscale private living with resort style pool on a shared property Whether you're here to soak up the sun or simply relax, Harbor House offers the perfect blend of comfort & convenience for your beach vacation

Private Retreat 1 house to beach. Beachside

Best kept secret on quiet street beachside away from busy condos. Only 1 house to wide pristine beach stretching for miles. 1 of 3 units 2nd story **May be some repair activity on the lower units thru November. None Nov 27-30 or wkends Beach supplies: towels, beach chairs, cooler. Walk to restaurants. W/D IN UNIT, Central AC, WIFI, park free Bedrooms: Comfortable mattresses. Black-out curtains. 2 bdrms with king beds. 3rd bdrm: large BONUS ROOM/laundry 2 twin beds, sliding door for privacy

King 1 Br/1Ba, Hot Tub - Close to Beach & Downtown

Whether you're Relocating, Vacationing, Working or Just Visiting, this cozy, luxurious, smart home is the perfect place to unwind. Featuring a hot tub, spacious private backyard, dedicated WFH office space, EV Charger, & fully stocked kitchen (ft. air fryer), you’ll find more amenities than I can list. A short 12 minutes from the #1 beach in the country, as well as a 12 minute drive from downtown and the gorgeous new Pier, you’ve truly found a gem in the heart of paradise. Go ahead and book!

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

The Tropical Oasis, w/ Solar Heated Pool and Games

Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, mosquito-free lanai. ​FUN & GAMES: Enjoy Billiards (Pool Table) 🎱, Foosball, Cornhole, board games, and 3 Smart TVs 📺. ​PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. ​ Essentials: ​🌞 Heated Swimming Pool (Private!) ​🎮 Billiard Table / Foosball Table / Cornhole / Boardgames and more! ​🛏️ 4 Queen/Full Beds ​🧺 Beach Amenities

Ocean View | Heated Pool | 3 Bed | Island Paradise

Your Private Oasis Awaits at Island Paradise! A haven of comfort and style in our meticulously curated Airbnb accommodations. Modern amenities and local charm, where each space tells a unique story. Whether you seek a cozy retreat, a vibrant urban escape, or a scenic getaway, our listings cater to every taste. Experience the warmth of hospitality and the joy of discovery as you make memories in homes that feel like your own. 6 person golf cart is available for your use!

Cozy funky duplex with KING bed

Escape to the charming town of Gulfport, Florida, and discover a hidden gem nestled in the heart of this vibrant community. Our eclectic studio offers a one-of-a-kind experience for those seeking comfort, style, and a touch of the extraordinary. The main highlight is the funky wallpaper and the luxurious king-sized bed, adorned with premium linens and plush pillows, ensuring a restful night's sleep after your Gulfport adventures.

[TRENDlNG] Modern 5BR Pool Villa + Arcade & Sauna

The Ultimate Vacation Awaits! Welcome to your home away from home—where comfort, fun, and relaxation all come together. Whether you’re here to unwind, explore, or make memories with friends and family, this place has you covered. Just 5 minutes from Madeira Beach and a short drive to Indian Rocks, Indian Shores, and Redington Shores—enjoy quick access to some of Florida’s best white-sand beaches and crystal-clear Gulf waters!

Coastal Cottage

Relax with the whole family or a peaceful couples get away. Great little Hideaway with a Large Pool, Club House, Playground for the little one. This cozy town home is 900 sq ft This is a fully furnished unit has everything you need to hide out or venture out to see all Tampa Bay has to offer. Completely renovated tin early 2023 everything was purchased new. Brands Like Macys, Crate and Barrel, My Pillow and others.

Villa Italia "Villas by Christine"

Perfect location, Charming Villa!! Guests are loving the newly renovated Villa Italia. Two luxury Masters with separate bathrooms - one upstairs & one down. Within the upstairs bedroom you have a queen size bed along with a full size couch for lounging during the day. We are pet friendly. Please let us know you will be bringing your pet. Pet fee of $100. can be paid beforehand or is due upon arrival.

10 minutes to Beaches! Basil House

Your Perfect Florida Getaway! Minutes from all the beaches Pinellas County has to offer! 1G Wi-Fi and a workstation in case you need to work while away. Less than 10 minutes to the beaches, and surrounded by great restaurants. You will enjoy every minute of your visit. Digital Guidebook with local recommendations! Located between St Pete and Clearwater while still close to the beach!