Villa holiday rentals in Pinellas County

4.94 out of 5 average rating, 143 reviews

An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.

Villa in St. Petersburg

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!!

4.99 out of 5 average rating, 100 reviews

The spacious living area features a dark leather sectional sofa with decorative cushions and a low coffee table at the center. Light hardwood flooring extends throughout. Sliding barn doors lead to an adjoining room with television and dining space, while soft lighting enhances the inviting ambiance.

Villa in Safety Harbor

Villa at Harbor House "Villas by Christine"

Welcome to The Villa at Harbor House, located just steps from Safety Harbor’s Main Street, ranked the #10 Main Street by USA Today in 2025. Enjoy convenient walkable access to charming shops, dining, and pubs. This villa is perfect for solo travelers or couples, offering a queen bedroom, fully stocked kitchen, spacious living room, smart TVs, full laundry, and more. Pet-friendly ($100 fee). Beach gear included. For larger groups, consider booking Villa Key West or Villa Italia, steps away.

The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.

4.98 out of 5 average rating, 162 reviews

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.

Villa in Indian Rocks Beach

4.92 out of 5 average rating, 92 reviews

The Emerald Villa, Eco-Luxury by the Sea

Eco-friendly, earth conscious seaside villa. Located just steps from the soft sands of the Gulf of Mexico beach, this exquisitely designed family home offers a luxurious yet sustainable escape. Encased in natural light, 4 bedrooms and 3 baths, the villa sleeps dynamic families and small groups in uncompromising comfort and style and provides all the zen essentials. In-house health suite with gym, infrared sauna and red light therapy available upon request at small additional daily fee.

Villa in Redington Shores

4.92 out of 5 average rating, 153 reviews

Beach so close! 1 house to beach Peaceful area

BEACH ACCESS IS STEPS FROM YOUR DOOR! A 30 second walk. 1 of 3 units in a private beachside villa tucked away on a peaceful street. A hidden gem away from busy condos. Wide beautiful beach goes for miles. Walk to many restaurants. Washer/dryer in unit. *Private patio. *Full sized kitchen. *Quiet ductless AC, *Free parking in front. *BEACH supplies provided. 1 bedroom super comfy queen bed, separate living room very comfortable pop-up sofa. 2 more units available; 1 bdm & 3 bdm.

4.91 out of 5 average rating, 127 reviews

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

4.98 out of 5 average rating, 47 reviews

An outdoor patio area features a private pool surrounded by a spacious deck. A seating arrangement with chairs and a table is positioned nearby, along with a sauna. The setting is complemented by lush green grass and a colorful sunset sky.

Villa in Seminole

[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!

5 out of 5 average rating, 43 reviews

A charming exterior of a townhome is presented, featuring a bright red front door. Lush greenery and colorful plants frame the pathway leading to the entrance, with a well-maintained lawn inviting guests to explore. The surrounding area is dotted with additional townhomes.

Villa in Palm Harbor

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.

A light-filled living area features a comfortable sofa adorned with decorative pillows. A wooden coffee table sits in front, complemented by a small plant. Sheer curtains frame the window, while a ceiling fan offers ventilation. A door leads to the outside, and a workspace is visible in the background.

4.99 out of 5 average rating, 98 reviews

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!

Superhost

Villa in Indian Rocks Beach

4.89 out of 5 average rating, 103 reviews

No Extra charge for dock use+Heated Saltwater Pool

2 King Beds 1 bath Vintage cottage w outdoor pool on intracoastal waterway. Perfect for 1-4 guests. Bring your small boat no charge. ( Must provide your own supplies/ ties/ bumpers) Only quiet respectful guests welcome. Work from home office with a beautiful view. This is someone's home half of the year, it's professionally cleaned, welcoming, down to earth. BTR1587

Superhost

A charming gazebo is positioned beside a serene pool, surrounded by vibrant greenery. The calm waters of Lake Seminole reflect the pastel colors of the sunset sky, while the gazebo offers shaded seating for relaxation.

4.91 out of 5 average rating, 118 reviews

Waterfront Heated Pool, Sleeps 20 - 4plex

Welcome to LAKESIDE RETREAT 4-plex, situated on a ⅓ acre next to Lake Seminole. Enjoy the perks of a private resort with amenities like a lakefront pool, a gazebo, and a cozy fire pit. The property is a 15-min drive to popular beaches, John’s Pass, and the Lake Seminole Park boat ramp. ✨ "Perfect place! Exceeded our expectations! thank you so much!" ✨