Guest house holiday rentals in Pinellas County

An exterior view of a well-lit garage with a modern stone façade. The white garage doors are flanked by tall, symmetrical planters with neatly trimmed shrubs. Soft illumination from the overhead lights enhances the clean lines of the architecture, creating a welcoming entrance.

4.88 out of 5 average rating, 187 reviews

Luxury Guest House close to the beach

This property has a wide room with a queen bed, 65" smart TV, safe box and extra bedding. It is included Netflix and wifi. A modern, spacious and comfortable bathroom with hot water. Includes shampoo, conditioner, body wash, extra paper, hair dryer and extra towels. This property also has a beautiful and modern kitchen completely remodeled and equipped with the basics to prepare your meals. it include microwave if you just want to heat up the food. If you like coffee you can enjoy a delicious coffee at any time, a variety of coffees, tea and chocolates are included. This property also has a sofa bed where two more people can sleep and is very comfortable. This property also includes a large outdoor terrace equipped with furniture to enjoy reading a book, have a delicious coffee, talk or simply enjoy nature. PETS ARE NOT ALLOWED, NO EXEPTIONS.

4.97 out of 5 average rating, 261 reviews

Centrally Located Cozy 1-bed Private Cottage!

This charming private cottage is ideally located near beautiful views, beaches, art, culture, restaurants, and a variety of family-friendly activities. Guests love the space for its peaceful ambiance, great location, and inviting outdoor areas. It’s a perfect stay for couples, solo travelers, business guests, or anyone looking for a cozy getaway. Enjoy private parking just steps from the entrance, along with a BBQ grill, a brand-new hot tub, and an outdoor gas fireplace—perfect for relaxing!!!

4.99 out of 5 average rating, 376 reviews

The image captures a serene outdoor area featuring a charming entrance to the cottage. Surrounding tropical plants and tall trees create a lush environment. A decorative fountain stands to the left, and comfortable seating under an umbrella adds to the inviting atmosphere.

Guest house in Largo

Paradise Cottage Largo Beaches 1 mile High ground

We are PARADISE COTTAGE, and the standards of super host are status quo! We're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 huge potted plants, many trees, etc we live in a lush tropical "Paradise". Our guests' highest praises include private, quiet, serene, safe and secluded; attributes we're fortunate to claim We have no neighbors while being so close to so much. Read the next section "The Space" to learn more.

Guest favourite

Guest house in Safety Harbor

Cozy Main Street Hideaway 4 guests, queen bed

Safety Harbor Main Street Hide Away. 3 blocks away from the beautiful Safety Harbor Main street and all its charm. Restaurants, boutiques, shops, bars, museums, the famous Safety Harbor Spa and pier, perfect place to spot manatees and have a gourmet coffee cup at the same time! Private Guest House with 900 sqft 1bed/1 bath .Ideal size for 1-2 couples or a family of 4 (kids are welcome). Private backyard patio.This is a non-smoking. Come enjoy! No pets allowed. Queen bed and a Murphy double bed

4.74 out of 5 average rating, 222 reviews

Guest favourite

A modern kitchen space features a marble countertop with two bar stools. Colorful wall art adorns the light-colored walls. Pendant lights hang above, casting a warm glow over the dining setup with turquoise dishes and a fruit bowl in view.

4.96 out of 5 average rating, 239 reviews

Quiet & Cozy Guesthouse minutes to the beach.

Newly remodeled, quiet and cozy guest house on a cul de sac. NO pets allowed under any circumstance. Great location close to shopping/restaurants, 4 miles to Gulf Blvd where you will find many beautiful beaches, Clearwater, St Pete etc. 1 Bedroom w/queen bed, and sofa bed in living room which pulls out to a queen bed. 2 TVs. Full kitchen with all the extras. Cable TV, WiFi, 1 private parking spot (can accommodate 2). Access to washer/dryer for stays 4 nights or more. Please no children under 8.

4.9 out of 5 average rating, 188 reviews

Cozy Renovated Studio – Private Entry + Parking

Welcome to our newly renovated studio guest house in the quiet Lealman neighborhood of St. Petersburg. Just 15 min from beaches and 10 min from downtown, 22 minutes from Tampa Airport. This compact, open-concept space features one queen bed and a sofa bed in the same room—no walls between sleeping areas. Ideal for 2 adults and 2 children, though 4 adults are welcome if comfortable with the shared layout. Enjoy private entry, 2 parking spots, fast Wi-Fi, and easy access to I-275 and local shops.

A spacious sleeping area features a large bed adorned with decorative pillows. A comfortable seating area with a gray sofa complements the room. Natural light enters through the window, illuminating a patterned rug on the floor, adding a touch of greenery.

4.98 out of 5 average rating, 252 reviews

The Florida Room. private entry.driveway parking.

Not a shared space. No "Plug ins' or harsh cleaning products . slightly sented detergents, No fabric softener. Close to Tampa, St. Pete , All beaches and Airport's Restaurants directly across the street. Publix, Starbucks within walking distance. Keyless private entry. Small fenced fenced area that is convenient for your pet. There's room enough for 1 car, 1 Animal Only. This includes service or non-service due to the size of the unit and consideration of the animals comfort. No guest Cats

Superhost

A well-designed fire pit area is surrounded by vibrant landscaping, featuring five blue adirondack chairs positioned around a stone circle. Lush palm trees provide a tropical ambiance, and a gravel path leads to the space, inviting relaxation in the private backyard.

4.83 out of 5 average rating, 433 reviews

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

Welcome to Casita Citron, a beautiful new tropical paradise in the heart of St. Pete! Tranquil & centrally-located: close to nature trails, shopping, downtown St. Petersburg, & Tampa. Minutes to St. Pete Beach, ranked #1 in USA! Washer & dryer on site. Private fully fenced in backyard with fire pit. Luxurious hot tub spa with speakers, water shooters, & LED lights. Heated outdoor shower. Memory foam mattress. SmartTV. Second queen size bed available upon request (AeroBed with foam topper).

Guest favourite

A private outdoor deck is shown with a mix of seating areas. A cozy sectional sofa is paired with square coffee tables, surrounded by decorative chairs. A large umbrella provides shade, while a tree adds a natural element to the space, creating an inviting area for relaxation.

4.92 out of 5 average rating, 143 reviews

Beachy Bohemian Bungalow with all the perks!

This cozy spot sits in a quiet neighborhood that boasts access to the Pinellas Trail Bike rental close Full kitchen w/ extras Queen bed w/ built in drawers Shelves & clothing rack Smart TV Full bath w/ walk-in shower Ample outlets/ USB Private deck for sun & shade Beach chairs, towels etc for beach Convenient to a dozen parks, beaches, shopping & restaurants. 2 miles to Madeira Beach 3 m - Johns Pass 1.2 m - Seminole City Center 7.6 m - St. Pete/ Clearwater Airport NO SMOKING NO PETS

4.86 out of 5 average rating, 147 reviews

Private Guesthouse in St. Pete w/ Pool & Jacuzzi

Enjoy privacy & tranquility in this detached guesthouse, with POOL & HOT TUB ACCESS! Ten minutes from Downtown, 17 minutes from St. Pete Beach, this spacious guesthouse has AC, its own Wifi, TV w/ Firestick, with a private entrance & parking. Host lives in a separate house on the property & is available if needed! We welcome guests to bring their beloved pets, however they cannot exceed over 50lbs. Sorry, pets are not allowed in the pool.

Guest house in Historic Kenwood

Charming apartment in Historic Kenwood

Cute, spacious apartment located in Historic Kenwood, which was named 2020 “Neighborhood of the year” by NUSA. Our apartment is above our large garage. Lots of charm and just enough space to spread out a little for some privacy. Located close to downtown, walking distance to lots of restaurants, breweries and bars but still a short drive to our beautiful beaches. You access the apartment through our side gate and up an exterior stairway.

4.97 out of 5 average rating, 383 reviews

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