Holiday Homes in Pinellas County

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Top-rated Holiday Homes in Pinellas County

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Guest favourite
Holiday home in Indian Rocks Beach
4.94 out of 5 average rating, 17 reviews

Stylish 2 Bedroom Beach Retreat

Experience the best of Indian Rocks Beach in this stylish 2-bedroom apartment, perfectly located just steps from the sand. This spacious retreat features 3 beds, 1 bath, and a comfy memory foam sleeper sofa—perfect for families or small groups. Walk across the street to the sand and enjoy nearby bars, restaurants, and shops. Around the corner, Kolb Park offers a playground, tennis, pickleball, and a skate park. Everything you need for the perfect beach getaway is right at your doorstep. BTR#1936

Top Guest favourite
Holiday home in Tampa
4.91 out of 5 average rating, 343 reviews

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.

Superhost
Holiday home in Clearwater
4.58 out of 5 average rating, 24 reviews

Adorable vacation guest suite close to beach

PLEASE READ "ABOUT THE SPACE." Beautiful vacation home, 13 mins (5.8 miles) away from Clearwater Beach. Close to Tampa International Airport. Close to Florida's major attractions - Busch Gardens in Tampa, 1.5 hours from Disney World, Universal Studios & Sea World in Orlando. Surrounded by Tampa Bay's recreational highlights - award winning beaches, boating, fishing, biking, golfing, jet ski rentals, water sports, beach activities, nightlife by Pier 60 surrounded by shops, restaurants, and bars.

Top Guest favourite
A cozy living room is displayed with a green sofa positioned beside a plant. A coffee table sits at the center, accompanied by a light fixture and a wall art piece. Natural light filters through the window, illuminating the warm wood flooring.
Holiday home in Tarpon Springs
4.97 out of 5 average rating, 142 reviews

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.

Top Guest favourite
A tranquil swimming pool is viewed from the patio, with clear water reflecting the sky's clouds. Lush palm trees and a calm waterfront line the background, creating a serene ambiance. The setting invites relaxation and offers a glimpse of the natural surroundings.
Holiday home in Tampa
5 out of 5 average rating, 36 reviews

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.

Superhost
A light-filled living area features a neutral-toned sofa with decorative pillows and a wooden coffee table. A stylish lamp provides a soft glow, while a small desk and chair are placed nearby. Artwork adorns the wall, contributing to the beach-themed decor.
Holiday home in St. Pete Beach
4.54 out of 5 average rating, 13 reviews

Beachy 'Sea Renity' 2

Enjoy a stylish experience at this centrally-located beach haven within walking distance to all the major local attractions. Gulf Sun Villas is a curated beach themed 1 bedroom/1 bath unit 2 blocks to the white sands of St. Pete Beach, TripAdvisor's #1 Beach in US (#5 in world). This beach getaway has designer furniture w/ a separate bedroom, full kitchen and bathroom. Perfect for singles, couples or a small family. Beach amenities may vary but we have beach towels, chairs and umbrella!

Guest favourite
The vibrant exterior of the house is highlighted by a welcoming yellow door and a staircase adorned with flower pots. Lush greenery surrounds the entrance, with a tiled driveway leading up to the home. Natural light enhances the inviting ambiance of the entryway.
Holiday home in Largo
4.96 out of 5 average rating, 84 reviews

New***Large House with Heated Salt Water Pool

The whole group will be comfortable in this spacious and unique space. The house has been tastefully and professionally decorated to ensure you can enjoy every corner of the house. * Two levels with two living/ family rooms to provide enough space for a large family or two. * Fully equipped kitchen. * Enough outdoor space in the front of the house and on the back. Two balconies and two huge decks. *Each bedroom has its own closet, so bring in your suitcases. * 10-15 min to the beaches.

Guest favourite
A tranquil beach scene is displayed, featuring soft, white sand leading to gentle waves under a clear blue sky. A few figures can be seen on the shoreline, with distant clouds adding texture to the horizon.
Holiday home in Indian Rocks Beach
4.86 out of 5 average rating, 57 reviews

Brand new vacation rental one block from the beach

Bring the whole family to this great place with lots of room for fun. 3 bedroom 2 bathroom rental a block away from the beach. Downstairs game room with pool table, ping pong, foosball and dart board! A lot of local restaurants, bars and stores within walking distance. Free parking on premise can fit up to 4 cars. This spacious rental can accommodate up to 8 people. Minimum 3 day rental, longer periods available. Perfect place for a family getaway, so many things to keep you busy! BTR#2064

Superhost
A spacious balcony overlooks Boca Ciega Bay, featuring a table with four black chairs. The sun shines brightly over the water, creating a serene ambiance. Lush greenery and a potted plant add a touch of nature to the scene.
Holiday home in St. Petersburg
4.92 out of 5 average rating, 90 reviews

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!

Top Guest favourite
Holiday home in Largo
4.92 out of 5 average rating, 52 reviews

Tropical Home for Family Getaway - 5 Min 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 to Indian Rocks and Clearwater Beach, with 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 (an additional $225 pet fee applies). Sorry, no cats.

Superhost
Holiday home in Clearwater
4.78 out of 5 average rating, 9 reviews

Orange Blossom Cottage heated pools 2 Min to beach

Escape to Orange Blossom Cottage, a freshly renovated 2-bedroom, 1-bath retreat just 2 blocks from Clearwater Beach. Relax in the bright living room with modern tile floors and stylish décor, rest easy in 2 spacious king bedrooms, and enjoy the charm of a retro aqua-tile bathroom. Surrounded by tropical gardens with access to 2 heated pools, our quiet cottage feels private yet is only steps from shops, dining, and the white sands — the perfect blend of relaxation and convenience.

Top Guest favourite
An inviting pool area is visible, enclosed by a screened lanai that allows for unobstructed views of the surrounding landscape. Comfortable seating arrangements are placed adjacent to the pool, while a coffee table displays a decorative arrangement, enhancing the relaxing atmosphere.
Holiday home in Safety Harbor
4.84 out of 5 average rating, 92 reviews

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!

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