Guest house holiday rentals in Clearwater

4.99 out of 5 average rating, 346 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.

A private patio area is surrounded by wooden fencing adorned with greenery. Two blue chairs are positioned at a round table, creating a serene space for relaxation. Natural light filters through the nearby trees, enhancing the inviting atmosphere of the outdoor setting.

4.98 out of 5 average rating, 242 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 house in Tarpon Springs

A comfortable living space includes a dark blue sofa with accent pillows and a coffee table. A dining area with wooden chairs is visible in the background, alongside a fully equipped kitchen. Light-colored cabinets and appliances complement the space.

4.86 out of 5 average rating, 105 reviews

Comfy 1BR Near Beaches & Sponge Docks

Enter your private oasis & enjoy our spacious 1 bd in scenic Tarpon Springs. Relax on the comfy couch or oversized chair. Treat yourself to free snacks, cold water & coffee, tea or hot cocoa w/ the Keurig in the fully equipped kitchen! Enjoy a hot shower or bath. Extra toiletries supplied. Games & books available. Comfortable Queen size bed ensures a great sleep. Only 3 miles from Howard Park Beach & Sponge Docks. Sunset Beach 1.3 miles. Innisbrook Golf Resort 3.9 miles! Private Entrance

4.96 out of 5 average rating, 215 reviews

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.

Guest house in Seminole

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.

4.93 out of 5 average rating, 125 reviews

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.

Guest house in Seminole

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

4.85 out of 5 average rating, 131 reviews

An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.

Guest house in Dunedin

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

4.97 out of 5 average rating, 196 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!

A guest house with bright yellow siding is set against a backdrop of lush trees. The entrance features a dark door and a small patio area with seating. Surrounding greenery adds a touch of nature, complemented by a white fence providing privacy.

4.97 out of 5 average rating, 145 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.

A light green room features a queen-size bed with a white quilt and decorative pillows. A small dining area with a round table and two chairs is visible alongside a neutral-toned sofa. Large windows provide natural light, and indoor plants are seen through the glass doors.

4.88 out of 5 average rating, 226 reviews

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!

4.95 out of 5 average rating, 247 reviews

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.

Guest house in Seminole

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.

Guest house in Town 'n' Country

4.99 out of 5 average rating, 267 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!

4.96 out of 5 average rating, 190 reviews

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guest house in Dunedin

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 has a walk in shower with stack washer and dryer. Spacious living area with a kitchenette. The property is an acre of lush tropical plants Conveniently located to the downtown & beach.All our units are non-smoking and vaping.

Popular amenities for guest house rentals in Clearwater

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A cozy guesthouse space features a spacious bed against a vibrant green wall. A sitting area is furnished with a neutral-toned couch and a small table. A kitchenette with wooden cabinetry includes a microwave and a small fridge, enhancing functionality.

4.86 out of 5 average rating, 126 reviews

Small but Spacious! Private guesthouse

A well-organized kitchenette is presented with a granite countertop, featuring a microwave, coffee maker, and a selection of coffee pods. A fire extinguisher and a sign indicating no smoking are visible nearby. A small shelf holds decorative items and a plant for subtle accent.

4.93 out of 5 average rating, 629 reviews

Tampa Carrollwood Studio

A serene entrance area features a welcoming white door framed by two vibrant hanging flower baskets. Two outdoor chairs are positioned around a small table, providing a cozy seating space. Lush greenery and decorative plants enhance the inviting atmosphere.

4.97 out of 5 average rating, 224 reviews

Paz Apartment WiFi & Parking

A cozy bedroom features a spacious bed with light linens and decorative pillows. Green accent walls complement framed artwork. Soft lighting is provided by two wall-mounted lamps, and a mirror reflects the inviting atmosphere. A small nightstand holds an alarm clock.

4.88 out of 5 average rating, 135 reviews

Cozy Renovated Studio – Private Entry + Parking

Guest house in Forest Hills

A cozy sleeping area features a spacious bed adorned with neutral-toned bedding and decorative pillows. An inviting seating area with a sectional sofa is visible, accompanied by a mounted television. Natural light streams through a window, enhancing the overall ambiance of the suite.

4.94 out of 5 average rating, 285 reviews

Cozy Suite

Superhost

A comfortable seating area is showcased with a modern brown sofa and a patterned chair. A large floral rug lies beneath, while a window with dark curtains invites natural light. A dining table with white chairs is visible in the background.

4.88 out of 5 average rating, 139 reviews

Private Seminole Heights Guest Home

Superhost

An outdoor space is depicted, featuring a pathway flanked by green artificial grass. A cozy seating area with vibrant blue cushions is visible on one side, complemented by a hot tub positioned nearby. Tall wooden fencing provides privacy, with trees in the background.

4.82 out of 5 average rating, 125 reviews

Grandma's House. Jacuzzi bathtub/Low cleaning Fee

The exterior of a cozy converted workshop features a gray wood-paneled facade with a vibrant yellow front door. Two chairs are positioned on the porch, beside a barrel and trash bins. A privacy fence can be seen in the background, surrounded by greenery.

4.84 out of 5 average rating, 870 reviews

Private & Cozy Tiny Home/Cottage

Guest house rentals with a patio

A spacious room features a comfortable bed with soft linens, complemented by a neutral-toned blanket. A kitchenette and dining area with a table are visible in the background. Light-colored walls enhance the room's brightness, while a hanging shelf provides additional storage.

4.9 out of 5 average rating, 186 reviews

Stylish guesthouse 1-BR 2 miles from Busch Gardens

Guest house in Central Oak Park

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, 225 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

A bright sleeping area features a comfortable bed with a white quilt and decorative pillows. Floral artwork is displayed above the bed. A mounted air conditioning unit and a small desk with a chair are included, along with a full-length mirror for added convenience.

4.99 out of 5 average rating, 190 reviews

Quiet and clean guest house!

Superhost

The entrance features a welcoming front porch with a hammock chair for relaxation. A small wooden table and chairs sit nearby under the black overhang. A potted plant adds a touch of greenery beside the door, while a BBQ grill is visible to the side.

4.87 out of 5 average rating, 296 reviews

Private Casita in the Heart of Tampa

A welcoming entrance to a bungalow is presented with a light blue door and decorative wall art. Surrounding greenery is visible, complemented by a pebbled pathway leading up to the stairs. White fencing provides privacy, enhancing the tranquil setting.

4.98 out of 5 average rating, 110 reviews

Beautiful Private Bungalow near Hyde Park & SOHO

A tiki-style patio features a wooden bar with a blue-tiled backsplash, illuminated by soft lighting. Decorative curtains in teal frame the area, enhancing its cozy ambiance. A small fountain adds a soothing element, surrounded by tasteful tropical decor.

4.96 out of 5 average rating, 188 reviews

Studio Bedroom - Private Bathroom , Full Kitchen.

Guest house in Riverside Heights

A bright living area features a gray love seat and a colorful area rug with abstract patterns. A wall-mounted television is positioned above a wooden console. A Murphy bed is neatly stowed away, and light filters through the window with wooden shutters.

4.99 out of 5 average rating, 170 reviews

Stay With Us and Enjoy Tampa’s Beautiful Fall

4.97 out of 5 average rating, 119 reviews

An inviting view into the living area is framed by a decorative arch. A vibrant green plant adds a touch of nature, while a cozy brown couch and accent chairs are arranged around a circular coffee table. Colorful artwork decorates the walls.

Guest house in Gulfport

Gulf Guesthouse - king bed, 3 blocks to downtown.

Guest house rentals with a washing machine and dryer

Guest house in Crescent Heights

A light-colored cottage is highlighted, featuring a welcoming red door. A paved outdoor area with a round glass table and four chairs is situated under a pergola with string lights, providing an inviting space for relaxation.

4.95 out of 5 average rating, 115 reviews

Crescent Heights Cottage

Guest house in South Seminole Heights

4.87 out of 5 average rating, 955 reviews

Seminole Heights Riverside Paradise w/Pool

Guest house in Historic Kenwood

The kitchen area features granite countertops and stainless steel appliances. An oversized kitchen island with two stools offers a space for meals. A door leads to the outdoor area, while a washer and dryer are conveniently situated to one side.

4.95 out of 5 average rating, 150 reviews

Oasis historic cottage w/Tropical Patio/Parking

Guest house in Tampa Heights

A modern living space is presented with a sleek kitchen and dining area. A large flat-screen TV is mounted on the wall across from a comfortable seating arrangement that includes a gray sofa and wooden chairs. Natural light is provided by nearby doors and windows.

4.94 out of 5 average rating, 173 reviews

Caffeinated Bungalito Near Armature Works|75in TV

Guest house in Historic Kenwood

The living area is furnished with a brown sofa and a matching loveseat, featuring colorful patterned cushions. A coffee table is centrally placed on a patterned rug. The open kitchen showcases dark cabinetry and modern appliances, with a small dining set of two tall stools at the counter.

4.98 out of 5 average rating, 128 reviews

Guesthouse in Downtown St Petersburg

Guest house in Pinellas Park

A cozy cottage is showcased, featuring a yellow exterior with white shutters. A white picket fence borders the front yard, which is adorned with green grass and shrubs. Two blue chairs are positioned on the porch, inviting relaxation.

4.87 out of 5 average rating, 277 reviews

pet friendly on an equestrian farm

A spacious living area is captured, featuring two black sofas, a rustic coffee table, and an inviting California king bed partially draped in a light canopy. A wooden dining area is visible in the background, complemented by artful decor and soft lighting.

4.95 out of 5 average rating, 149 reviews

The Hawk's Nest at Alligator Creek