Guesthouse holiday rentals in Dunedin

4.9 out of 5 average rating, 420 reviews

A vibrant sunset paints the sky in warm hues of orange and yellow, as the sun sinks below the horizon over a tranquil ocean. The image conveys a serene coastal atmosphere, resonating with the proximity to nearby beaches.

Guesthouse in Clearwater

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

4.99 out of 5 average rating, 344 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.

Guesthouse in Palm Harbor

A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.

4.86 out of 5 average rating, 160 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

4.97 out of 5 average rating, 334 reviews

9 Mins to Downtown, Full Kitchen, KingBed, Balcony

Freshly remodeled second story apartment in a charming 1920's guest house located in trendy Seminole Heights just North of downtown Tampa with easy on/off from I-275. Features a full kitchen, living room, king bedroom, bathroom, and balcony. Walk to restaurants, hip bars, and shops, or stroll the tree-lined streets of 100+ year old houses. Minutes from all Tampa has to offer: Busch Gardens, Zoo, Downtown, Riverwalk, Hard Rock Casino, USF. Come and relax at this inclusive and welcoming space.

Guesthouse 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.

4.85 out of 5 average rating, 101 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, 211 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.

4.84 out of 5 average rating, 126 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.

4.97 out of 5 average rating, 186 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!

4.97 out of 5 average rating, 140 reviews

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.

Guesthouse in Clearwater

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 bright living room features a light-colored sofa and a round dining table. A large mirror reflects light, enhancing the space. A 55-inch Smart TV sits on a wooden console, while decorative plants and books add a touch of greenery and character.

4.91 out of 5 average rating, 119 reviews

1 Bedroom Apartment in the heart of St. Pete

Charming 1 bedroom 1 bath apartment centrally located in the heart of vibrant St. Pete. Near Downtown, Edge District, Grand Central, Crescent Lake, Tropicana Field, Vinoy Park, and the Pier, you'll have convenient access (5 minute drive) to St. Pete's best restaurants, trendy cafes, exciting nightlife, and sunny waterfront parks. World class beaches are a 15 to 20 minute drive away. Thoughtfully furnished for both a relaxing getaway or a remote work trip.

4.88 out of 5 average rating, 223 reviews

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.

Guesthouse in Clearwater

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!

Guesthouse in Town 'n' Country

4.98 out of 5 average rating, 259 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!

Popular amenities for Dunedin guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A sleeping area features a spacious bed adorned with multiple pillows and a decorative bolster pillow. A collection of framed artwork is displayed on the wall above. A bedside lamp and a wooden nightstand are positioned nearby, adding functionality to the space.

4.79 out of 5 average rating, 117 reviews

Sonia's Little House

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, 133 reviews

Cozy Renovated Studio – Private Entry + Parking

Guesthouse in Tampa Heights

A serene pool area features a shimmering blue pool surrounded by lush greenery, including tropical plants. Two lounge chairs are positioned nearby on a brick patio, providing a comfortable spot for relaxation. A detached structure is visible in the background, set amongst a canopy of trees.

4.88 out of 5 average rating, 391 reviews

Pool Side Getaway, Walk/Bike Tampa River Walk

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.

4.94 out of 5 average rating, 284 reviews

Cozy Suite

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.

4.94 out of 5 average rating, 174 reviews

Now Reopened! - The Highland Hideaway

Guesthouse 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, 275 reviews

pet friendly on an equestrian farm

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, 864 reviews

Private & Cozy Tiny Home/Cottage

A well-equipped kitchen features sleek white cabinetry and countertops. Stainless steel appliances, including a microwave and a gas stove, are present. Decorative elements, such as red kitchenware and glassware, are arranged on open shelves, creating an organized and inviting space.

4.91 out of 5 average rating, 182 reviews

red comfort trip" 5 minutes to Bush gardens

Guesthouses with a patio

Guesthouse 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, 220 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

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, 120 reviews

Cozy Tropical 2BR Casita + Hot Tub • Near Downtown

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.

5 out of 5 average rating, 112 reviews

Stylish☀Mini Mint Bungalow☀10 mins from downtown

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, 181 reviews

Quiet and clean guest house!

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.

4.89 out of 5 average rating, 292 reviews

Private Casita in the Heart of Tampa

4.86 out of 5 average rating, 114 reviews

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.

Guesthouse in Seminole

Luxury Guest House close to the beach

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.

4.9 out of 5 average rating, 139 reviews

St Pete Casita Studio with Salt Water Pool & Yard

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, 147 reviews

Relaxing & Charming Hideaway

Guest house rentals with a washing machine and dryer

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, 184 reviews

Stylish guesthouse 1-BR 2 miles from Busch Gardens

Guesthouse 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

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.

4.84 out of 5 average rating, 362 reviews

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

A modern two-story house features a clean white exterior and a staircase leading to the upper level. Potted plants flank the entrance, while outdoor seating awaits nearby, creating a welcoming space for relaxation.

4.87 out of 5 average rating, 192 reviews

Dee's 5-star Tampa Location Unit 1

Guesthouse in Bayshore Beautiful

An outdoor patio area is enclosed by a wooden fence, featuring a fire pit surrounded by two white adirondack chairs. Lush greenery and small shrubs border the space, which is accentuated by a stone path and grassy patches under a clear blue sky.

4.84 out of 5 average rating, 255 reviews

La Casa Azul - Private Detached Guest House

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.

4.95 out of 5 average rating, 167 reviews

Caffeinated Bungalito Near Armature Works|75in TV

Guesthouse in Historic Kenwood

A bright living space features hardwood floors and a comfortable seating area with a small coffee table. Natural light filters through the large windows, showcasing a cozy atmosphere. Outdoor views highlight the charming architecture of the surrounding neighborhood, inviting relaxation with a morning drink.

4.9 out of 5 average rating, 271 reviews

Walk to St. Pete's Grand Central from Historic Apt

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.