Guesthouse holiday rentals in Pinellas County

4.99 out of 5 average rating, 362 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.

Guesthouse 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.

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, 108 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.

4.98 out of 5 average rating, 224 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, 227 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.

The kitchenette features green cabinets and a wooden countertop, equipped with a microwave and coffee maker. A window provides natural light, while open shelves display glassware and decorative items. A mini-fridge and amenities create a functional and cozy cooking space.

4.97 out of 5 average rating, 103 reviews

The Perfect Studio

Enjoy an amazing experience at this centrally-located, newly renovated, private studio apartment! Adorable kitchenette, dreamy walk-in tiled shower, and close to everything!! •1.7 miles from Sunken Gardens •3.2 miles from The Dalí Museum •2.8 miles from Tropicana Field •2.5 miles from the best shopping, restaurants, and coffee shops in downtown St. Pete and our gorgeous pier! •10 miles from our World Famous Bay Beaches All while staying in a relaxing neighborhood. Come live like a local!

Guest favourite

The living area is furnished with a light-colored sofa and an ottoman, offering comfortable seating. A smart TV is mounted on the wall, and a wooden dining table is visible nearby. A ceiling fan provides airflow, with natural light filtering through a nearby window.

Guesthouse in Clearwater

4.93 out of 5 average rating, 103 reviews

Adorable Vintange Style guest house-King size bed

Welcome to the beautiful city of Clearwater, and to our newly renovated Vintage Style Guest house. Conveniently located within 0.5 miles or 7 minutes walking to clearwater downtown, and 3 miles or 7 minutes driving to the famous and award winning Clearwater beach. Easy access to local restaurants, bars, stores, and parks. This comfortable guest home features unique layout with Vintage-modern decor, free WiFi, smart TV, LVT flooring and sleeps up to 4 people. It also offers one free parking.

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, 244 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!

4.98 out of 5 average rating, 220 reviews

Centrally Located Cozy 1-bed Private Cottage!

This adorable cottage is close to great views, art, culture, restaurants, dining, the beach, and family-friendly activities! You’ll love this private cottage because of the location, the ambiance, and the outdoor space. This cozy cottage is good for couples, solo adventurers, business travelers, and anyone needing a cozy place to stay! Parking is just steps away from the cottage with a private entrance. BBQ is available, new hot tub, and an outdoor gas fireplace for a relaxing evening!

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.

4.85 out of 5 average rating, 151 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

A charming house features a light blue exterior with white trim and is adorned with festive decorations. Lush greenery surrounds the property, with a well-maintained front lawn and a pathway leading to the entrance. A large tree offers shade in the front yard.

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 two-story house is depicted, featuring white siding and a green accent on the lower level. The driveway is paved with light-colored bricks, leading to a garage with multiple doors. Lush greenery surrounds the property, providing a serene environment.

4.95 out of 5 average rating, 256 reviews

Private Apt/3miles from beaches/Treehouse.like

Live Like the Locals in the small town of Seminole. Our home sits on 1 acre of property conveniently located across from 3 BEAUTIFUL county parks. You will be in a city and feel like your in the country. We are 3 miles from sandy white Gulf Beaches. Less than 2 miles from SPC Seminole campus. Perfect for CE classes etc.. NEW MALL just opened 1.8 miles away. Lived and worked out of our home for over 50 years and would be able to facilitate.

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.