Guest house holiday rentals in Pinellas County

4.99 out of 5 average rating, 364 reviews

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.

4.97 out of 5 average rating, 225 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!!!

A warm living room is presented, featuring a light-colored sectional sofa and a dark blue armchair. A coffee table is centered on an area rug, adorned with decor. Two large windows allow natural light to fill the space, complemented by framed artwork on the wall.

4.99 out of 5 average rating, 109 reviews

Kenwood Retreat - 1BR carriage house

This newly constructed carriage house was built to embrace the character and charm of the main house, a 1928 craftsman bungalow. Your 2nd floor 1 BR apartment is well appointed with a full chef's kitchen, a living room with a pull-out sofa, and washer/ dryer. Enjoy a morning cup of coffee or a glass of wine in the evening on the large porch. 2 min walk to Grand Central restaurants, coffee shops, boutiques, or grab a bike or scooter for a 5 min ride to Downtown St. Pete or 15 to the beaches.

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, 226 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

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, 230 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 8.

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 248 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. EVERYONE is welcome here. Come & enjoy!

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, 140 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

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.

4.86 out of 5 average rating, 156 reviews

Luxury Guest House close to the beach

Welcome to our beautiful beaches of Seminole city. This property is well located just 5 minutes away from the beach. The unit is on the corner with easy access to a main ave. There is a wide variety of bars, restaurants and supermarkets. Also it is newly renovated including new appliances and furniture. In addition there is a private entry and fenced outside seating area that’s perfect to relax. For security the property has smoke detector and fire extinguisher. Pets are not allowed

Guest favourite

A spacious sleeping area features a modern white bed dressed in a black coverlet, complemented by matching throw pillows. A sleek dresser stands nearby, and the wall behind the bed showcases a stylish wavy pattern in black and silver. A small seating area with two chairs is visible.

Guest house in Tampa

4.97 out of 5 average rating, 353 reviews

Romantic Getaway*FREE Decor AnyOcassion*Relax Bath

A cozy place to have your vacation in Tampa, private entrance and parking.We include decorations for all occasions:birthday,wedding,special day, show your love, and more! Contact us with your ideas and we'll make this trip unforgettable! Located in a central area of Tampa, close to Bush Garden/Adventure Island, Raymond James Stadium,Tampa International Airport,Ybor City,Downtown Tampa,Clearwater Beach and more! Peaceful and centrally-located place to enjoy as a couple to your liking.

A cozy living area features an inviting beige armchair and a small round table set with placemats. Light streams in through a nearby door adorned with a wreath, illuminating the space with a natural glow. A patterned rug adds texture to the wooden floor.

4.98 out of 5 average rating, 261 reviews

Historic Old Northeast Get A Way

Carriage house converted to cozy updated 1 bedroom plus separate den/office above garage apartment in historic Old Northeast. The den/office has a new queen Murphy bed which will allow a second private sleeping space. Two blocks walking distance to Vinoy Waterfront Park and downtown St Pete. Twenty minute car ride to the beautiful Gulf Beaches or downtown Tampa. Great weekend get-a-way or longer term rental. Parking is available on the street with a parking permit which we provide.

A cozy bedroom features a spacious bed adorned with decorative pillows and a bright, textured quilt. Wall decor includes framed artwork and decorative plates that add charm. A bedside lamp rests on a nightstand, providing soft illumination, while natural light filters through sheer curtains.

4.98 out of 5 average rating, 359 reviews

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.