Guest house holiday rentals in Pinellas County

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Top-rated guest house rentals in Pinellas County

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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Guest favourite

Guest house

4.88 out of 5 average rating, 283 reviews

Private Guest Studio w/Courtyard

Enjoy your own private guest studio separate from the main house (no main house access). Located 1 mile from downtown and 1/2 mile from Tampa Bay. Guest studio includes one queen size bed, one full bathroom with shower (no tub), brand new air conditioner, mini fridge, 32" smart TV (login to your favorite streaming options and enjoy, no cable provided), a microwave and a coffeemaker. Great walking ability. We do not allow animals, any pet related questions please inquire with us prior to booking!

Guest favourite

Guest house

4.88 out of 5 average rating, 166 reviews

Casa Magnolia- Cute and spacious remodeled unit

Perfect St. Petersburg getaway! This spacious and completely remodeled unit is located in a quiet residential area but is close to everything the area has to offer. Downtown St. Pete with it's new pier, spa beach, waterfront parks, many restaurants and breweries is less than 5 miles away. Sawgrass Park and Weedon Island Nature Preserve (~2 miles) offers great nature trails, kayaking, fishing and birding options. Some of the best beaches in the world are less than 30 minutes away. TPA is 20 mins.

Guest favourite

Guest house

4.98 out of 5 average rating, 206 reviews

Cozy Guesthouse Near Downtown (Non-Toxic)

Come relax in this calm, newly renovated guest suite. Clean, natural, & chemical free - diffusers and oils available on site. Amenities like central a/c, laundry, private patio, full kitchen, Netflix & Hulu. A short 5 minute drive from downtown - near tons of local restaurants, entertainment, and beaches. St. Pete loves the local vibe, be sure to check out our visitors guide for suggestions on spots to see while you’re here. It doesn’t get any better than St Pete! Book your stay with us today!

Guest favourite

Guest house

4.96 out of 5 average rating, 179 reviews

Quiet & Cozy Guesthouse minutes to the beach.

Newly remodeled, quiet and cozy guest house on a cul de sac. Great location close to shopping/restaurants, 4 miles to Gulf Blvd where you will find many beautiful beaches, Clearwater, St Pete etc. 1 Bedroom, queen bed, and sofa bed in living room which pulls out to a queen bed. Full kitchen with all the extras. Cable TV, WiFi, 1 private parking spot (can accommodate 2 or recreational vehicle just need a heads up). Access to washer/dryer for stays 4 nights or more. No pets, no children under 12.

Guest favourite

Guest house

4.96 out of 5 average rating, 174 reviews

Casita Blue

Stay in Palmetto Park next to the Grand Central District and the Warehouse Arts district. This walkable neighborhood in St. Pete offers a wide variety of restaurants, bars and breweries. Downtown St. Pete entertainment is less than two miles away, and you can drive/rideshare to some of the best beaches in the world in 15 minutes. Tamp Int'l Airport is 30 minutes, Disney is 90 min, and Tropicana Field is 3/4 mile. This guesthouse offers an outdoor parking spot and w/d located in the garage.

Superhost

Guest house

4.83 out of 5 average rating, 293 reviews

Papa Bear's Cottage Two Bedroom Vacation Rental

A simple, yet magical second-story guesthouse, nestled into a yard of Spanish Moss and Magnolia trees, above a garage (no one will be in the guest house but you!). Minutes from downtown Tarpon Springs and the famous Sponge Docks, and 15 minutes from beautiful Gulf beaches, 30 minutes from Clearwater Beach. Hunkered in at the end of a private drive, on over two acres of quiet, enchanting land. You and your crew will enjoy the respite, nature, and coziness of Papa Bear's Cottage!

Guest favourite

Guest house

4.97 out of 5 average rating, 104 reviews

Cozy 2 Bedroom - 12 Minutes from Clearwater Beach

Make your vacation relaxing, fun and easy! - Kick back in the hammock or have some coffee with loved ones in the peaceful private backyard. - Take the 12 minute drive to the beach with the provided boogie boards, chairs and sand toys. - Take a walk or bike ride on the gorgeous Pinellas Trail. You'll also find some of the best coffee, food and ice cream on the way. -Golf courses close by. This is a separate unit that shares a driveway and parking area with the front house.

Guest favourite

Guest house

4.9 out of 5 average rating, 238 reviews

Crescent Heights/St. Petersburg Entire Guest House

If you are looking for a clean, cute place to stay, you’ll love our studio guesthouse! Our contemporary 350-square-foot remodeled garage apartment is located in the tranquil, tree-lined neighborhood known as Crescent Heights. We are a 5 minute ride to downtown St. Pete where you can sample many great restaurants, breweries, museums and shops. The Gulf beaches are 25 minutes away and downtown Tampa is a 40 minute ride. Unit has private parking and queen size bed.

Guest favourite

Guest house

4.98 out of 5 average rating, 101 reviews

2 bedroom guesthouse in hip Grand Central District

Walkable to the beating heart of the artsy Grand Central and Edge district of St. Pete. Newly built (2022) garage apartment with two bedrooms, one-bathroom, full-sized kitchen with brand new appliances. The bedrooms have all the comforts of a hotel with a personality that matches the vibrancy of the Grand Central community. This space is perfect for travelers looking for a local vibe. Stay in the sunshine inspired apartment and soak up all St. Pete has to offer.

Guest favourite

Guest house

4.95 out of 5 average rating, 165 reviews

Tiki Hut Cottage

This unit private vacation rental is privately located on the property, plenty of space for 4 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom whas a walk in shower with stack washer and dryer. Spacious living area with a fully functional kitchen. The property is an acre of lush tropical plants Conveniently located to the downtown & beach We allow a dog 35 lbs or less. all our units are non-smoking and vaping.rebate vacation

Guest favourite

Guest house

4.98 out of 5 average rating, 163 reviews

Entire Guest House near Tampa airport

Welcome to our charming guest house! Located just 12 minutes away from Tampa Airport, 20 minutes from Raymond James Stadium, and a quick 35-minute drive from Clearwater, our entire guest house offers you convenience and comfort. With a private entrance, you'll have all the privacy you need. Whether you're here for a game, a beach getaway, or to explore the city, our cozy space is your perfect home base. Book now for an unforgettable stay!

Guest favourite

Guest house

4.9 out of 5 average rating, 186 reviews

A Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok!

We are grateful to share that this beautiful upstairs cottage unit is Guest Ready!! It was not damaged by the storms and we are excited to start taking reservations again! Many establishments throughout the Gulf beach areas have reopened. Your stay provides the much needed support our local businesses appreciate and need as they recover. Please note that there is renovation work ongoing to the downstairs cottage.