
Guesthouse vacation rentals in Pinellas County
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Top-rated guesthouse rentals in Pinellas County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Minutes to Beaches w/King Bed Private Updated
This private home away from home near pristine beaches sits behind the main house in a quiet neighborhood conveniently located near downtown Clearwater, Clearwater Beach, Tampa, St Petersburg, Dunedin, Tarpon Springs, and other great towns. Restaurants, shopping, & entertainment venues. • Clearwater Beach= 4 miles / 8 minutes • Downtown Dunedin= 3 miles • Honeymoon Island= 9 miles • Tarpon Springs Sponge docks= 14 miles • Tampa Airport (TPA)= 14 miles • St Pete/Clearwater Airport (PIE)= 9 miles

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.

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.

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!

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.

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

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.

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

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!

Gulf Guesthouse - king bed, 3 blocks to downtown.
Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!

Cottage on Pinellas Bike Trail
This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!

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.
Popular amenities for Pinellas County guesthouse rentals
Family-friendly guest house rentals

A slice of paradise!

Cozy Coastal Casita

Tiki Hut Cottage

Guest House in prime location!

Historic Old Northeast Get A Way

The Lassing House

Relaxing & Charming Hideaway

2 bedroom guesthouse in hip Grand Central District
Guest house rentals with a patio

Restful Palms

Cozy Tropical 2BR Casita + Hot Tub • Near Downtown

Beautiful Studio near Tampa Airport (TPA)

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

Cozy Renovated Studio – Private Entry + Parking

Peaceful & Private Dreamy Lodge TPA, DWTN, Beaches

St Pete Casita Studio with Salt Water Pool & Yard

Comfy 1BR Near Beaches & Sponge Docks
Guest house rentals with a washer and dryer

Pool & Close to dtwn w/2 Bikes

Private 2 BR Backyard Oasis, Walk to Downtown!

Charming Guest House in Tampa

Cute home in historic neighborhood

New private guesthouse walk to downtown Dunedin

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

Private Guest House

Lovely Guesthouse
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
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