Guesthouse holiday rentals in Clearwater

4.99 out of 5 average rating, 355 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 hot tub is positioned beside a fire pit, surrounded by greenery and decorative lighting. A projector screen displays images, creating an inviting atmosphere for outdoor entertainment. The space is enhanced by potted plants and gravel pathways, offering a serene retreat.

4.93 out of 5 average rating, 200 reviews

HOT TUB & Free Wine !, Ping-Pong, Outdoor Theatre

You will Experience serenity at The Loft House Retreat! Amidst lush Florida plants, unwind in a hot tub, challenge friends to ping pong, or cozy up by the fire pit and Projector. Inside, enjoy 2 full beds & refresh in a full bathroom with a walk in Shower. Explore Tampa's gems: Busch Gardens, Downtown Tampa, Waterstreet, Armature Works, Zoo Tampa, The Florida Aquarium, Raymond James Stadium, Sparksman Wharf, Michelin-starred restaurants, and historic eateries. Book your unforgettable escape now!

4.96 out of 5 average rating, 227 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.

Guesthouse 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.

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.

4.85 out of 5 average rating, 383 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).

4.83 out of 5 average rating, 149 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.

Guesthouse 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.

4.98 out of 5 average rating, 214 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!

Guesthouse in Safety Harbor

A welcoming entrance is marked by a rustic wooden sign that reads 'Guest Entrance.' In the background, a charming guest house is visible, surrounded by lush palm trees and green foliage, creating a serene outdoor space.

4.73 out of 5 average rating, 211 reviews

Cozy Main Street Hideaway

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 (Family with kids welcome). Private backyard patio with fire place. This is a non-smoking. Come enjoy! No pets allowed.

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.

4.97 out of 5 average rating, 334 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.

Superhost

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, 153 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 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, 152 reviews

The Hawk's Nest at Alligator Creek

Nestled in the heart of Clearwater, Hawk’s Nest is a peaceful, private artist's retreat reminiscent of Tennessee or North Carolina. Surrounded by nature, it feels like living in a treehouse! Sports fans will love being near two Spring Training stadiums and just 25 minutes from Raymond James. Only 20 minutes to the beach, and centrally located for shopping and activities. A safe, gated property offering peace and convenience. Unforgettable! Also available for longer stays.

A private outdoor area features a golf putting green with a textured surface, a jacuzzi with soft blue hues, and a wooden pergola. Near the pergola, a grill is provided alongside comfortable seating. Vibrant green walls and string lights enhance the inviting atmosphere.

4.97 out of 5 average rating, 116 reviews

"Luxury Casita/Jacuzzi/Bush Gardens/USF/Casino"

Welcome to Tampa Luxury Casita, a stylish and centrally located retreat featuring a relaxing jacuzzi and a private golf putting green. Located within walking distance to Busch Gardens, this beautifully designed space offers modern amenities, cozy comforts, and easy access to top attractions. Whether you're here for a weekend getaway or an extended stay, our casita promises a luxurious and unforgettable experience. Book now and enjoy the best of Tampa Bay!

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.

4.89 out of 5 average rating, 238 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!

Popular amenities for Clearwater guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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, 238 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

5 out of 5 average rating, 215 reviews

A bright living area is showcased with a white sofa and two leather chairs arranged around a circular coffee table. Light curtains frame a window above a cozy daybed. A small workspace with a TV is visible in the corner, enhancing the space's functionality.

Guesthouse in Dunedin

Bay Suite in Heart of Dunedin

A bright and airy kitchen and living area are visible, featuring white cabinetry and modern stainless steel appliances. A cozy sectional sofa is positioned near a window, while a subtle area rug adds warmth to the space. A flat-screen television is mounted on the wall, enhancing the functional layout.

4.98 out of 5 average rating, 43 reviews

New private guesthouse walk to downtown Dunedin

A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.

4.91 out of 5 average rating, 154 reviews

St Pete Casita Studio with Salt Water Pool & Yard

4.91 out of 5 average rating, 311 reviews

Walk to Downtown St Pete-Nightlife, Bay & Museums

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.

4.94 out of 5 average rating, 97 reviews

Adorable Vintange Style guest house-King size bed

Superhost

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, 891 reviews

Private & Cozy Tiny Home/Cottage

4.93 out of 5 average rating, 167 reviews

Bright 1BR Cottage — 10 min to Downtown & Beach

Guesthouses with a patio

A modern kitchen area is showcased, featuring sleek white cabinetry and a variety of appliances including a refrigerator, microwave, and coffee maker. The open layout allows for easy movement, with a plush recliner positioned nearby and a wooden table providing workspace.

4.95 out of 5 average rating, 104 reviews

Modern 1 BR Studio - Self-Check in and Parking.

4.99 out of 5 average rating, 98 reviews

Guesthouse in Uptown

Family Friendly DTSP 2/1 Neighborhood Apt

Guesthouse in Historic Kenwood

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, 104 reviews

Kenwood Retreat - 1BR carriage house

A hot tub is surrounded by lush greenery and vibrant red flowers, creating a serene atmosphere. A tall palm plant is visible beside the tub, complementing the tropical landscape. A large umbrella is positioned nearby, providing shade on bright sunny days.

4.96 out of 5 average rating, 134 reviews

Cozy Tropical 2BR Casita + Hot Tub • Near Downtown

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.

4.89 out of 5 average rating, 149 reviews

Cozy Renovated Studio – Private Entry + Parking

Guesthouse in North Tampa Heights

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.

5 out of 5 average rating, 217 reviews

Quiet and clean guest house!

The bright living area features a green sofa with a decorative pillow, a white coffee table, and a dining table with four chairs. Vibrant wall art enhances the space, complemented by large windows allowing natural light. A doorway leads to the private side yard.

4.98 out of 5 average rating, 166 reviews

Relaxing & Charming Hideaway

A charming guest house with light blue accents stands surrounded by lush greenery. The entrance features a welcoming blue door, flanked by neatly arranged planters with vibrant plants. Decorative elements are placed on the exterior walls, enhancing the overall appeal.

4.95 out of 5 average rating, 184 reviews

The Highland Hideaway

Guest house rentals with a washing machine and dryer

Guesthouse in Old Seminole Heights

A charming guesthouse is seen from the front yard, featuring a green exterior with white trim. A welcoming porch is adorned with two chairs, and gentle landscaping with shrubs compliments the space. The surrounding grass is well-kept, enhancing the inviting presence of the home.

4.99 out of 5 average rating, 130 reviews

Stylish☀Mini Mint Bungalow☀10 mins from downtown

Guesthouse in Logan Gate Village

A cozy bedroom features a spacious bed with plush pillows, illuminated by soft blue lighting from the headboard. A bedside lamp provides additional light, while artwork adorns the wall above the bed. Ample closet space is visible next to the door.

4.98 out of 5 average rating, 110 reviews

Charming Guest House in Tampa

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

Guesthouse 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, 191 reviews

Caffeinated Bungalito Near Armature Works|75in TV

Guesthouse 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.

4.93 out of 5 average rating, 300 reviews

Cozy Suite

Guesthouse in Historic Kenwood

The exterior of a newly built garage apartment is presented, featuring a modern design with light green siding. A single-car garage is visible, flanked by two small windows above. Natural light illuminates the gravel driveway and surrounding landscaping.

4.98 out of 5 average rating, 122 reviews

2 bedroom guesthouse in hip Grand Central District

4.86 out of 5 average rating, 417 reviews

The exterior of the guest house is framed by lush greenery and palm plants. A patio area is visible, featuring an umbrella and white chairs. A grill is positioned beside the entrance. Natural light streams in through large sliding doors, leading to the yard.

Guesthouse in Odessa

Private Guest House