Cottage holiday rentals in St. Petersburg

4.95 out of 5 average rating, 140 reviews

A cozy living space features a well-equipped kitchenette with modern appliances, including a coffee maker and microwave. A dining table with two chairs is positioned beside expansive windows. A spacious bed occupies the corner, complemented by light-colored bedding and gentle lighting from ceiling fans.

Cottage in Largo

Walk to beach shops food drinks “The Sweet”

Cozy, romantic, 1 king bed, super cute and super sweet! Just a short walk to beautiful Indian Rocks Beach, nature parks with trails, shopping, orange grove, and many restaurants and fun beach bars! Guests have private entrance, private full bath, kitchenette, sofa sleeper, large back yard with fire pit, bbq grill, beach chairs, wagon and cooler. Zoning permits 2 people per bed only and one on futon. All guests must be listed on the reservation. No Pets allowed. Florida State License # DWE6215889

4.96 out of 5 average rating, 163 reviews

A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.

Cottage in Gulfport

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

Cottage in Pass-a-Grille Beach

The image captures the tranquil waterway with gentle ripples reflecting the sky. In the background, a charming beach cottage is framed by palm trees and boats docked nearby, creating a serene waterfront scene.

4.97 out of 5 average rating, 157 reviews

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Cottage in Seminole Heights

4.95 out of 5 average rating, 406 reviews

Historic Heights Hideaway • Early Check-in

A perfect balance between suburban serenity & urban convenience in this historic Tampa neighborhood. Central air, Roku, strong Wi-Fi, coffee, tea, snacks. Easy self-check-in. The ideal home base for your Tampa adventures. Walk to Hillsborough River, Garden Center, & Florida Ave hotspots. 5 min to Zoo, 10 min drive to Amalie Arena, Busch Gardens, Ybor City, Ray Jay Stadium, Florida State Fairgrounds/Amphitheater, Riverwalk & Airport; 35 min to St Pete & nations best beaches, 70 min to Disney.

4.97 out of 5 average rating, 129 reviews

A serene lakefront view is framed by tall trees draped with Spanish moss. A wooden dock extends into the calm water, providing a space for relaxation. Soft shadows are cast across the lush green lawn, inviting guests to enjoy the peaceful surroundings.

Cottage in Lutz

A little piece of Heaven

2 people max cozy cottage with all the amenities of home with a lakefront view. There's a firepit for those colder nights and kayaks & peddleboats for the more adventurous ones, or just sit back and take in some sun on our beautiful dock. Centrally located in between the Veterans Expressway and I 275, minutes from shopping, Lake Park, Adventure Island and Busch Gardens ...Lutz has something for everyone, don't let your friends and family stay in a hotel, we've got it all waiting right here!

Cottage in Euclid Place - St. Paul

A cozy living room features a tan sofa positioned across from a purple armchair. A round coffee table is centered on a light-colored rug. Colorful artwork adorns the wall, while a floor lamp provides warm lighting. The space is brightened by natural light through a window.

4.95 out of 5 average rating, 125 reviews

Artsy guest house; near downtown w/ private patio

This uniquely decorated guest house is a private oasis with a lovely, private patio. The house is decorated with Latin American art from the owner's collection & travels. Only 11 blocks to downtown and very close to grocery stores, art galleries and all the night light life St. Pete offers. The home has a full kitchen and a very comfortable bedroom for one or two people. A perfect location for those that want to experience a comfortable and relaxing place. Only 12 block walk to Tropicana.

4.97 out of 5 average rating, 172 reviews

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

4.97 out of 5 average rating, 225 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Cottage in Bayshore Beautiful

A comfortable seating area features two light-colored sofas with throw pillows, arranged around a rustic wooden coffee table. A decorative screen provides partial division from other spaces, and a textured rug is laid beneath the furniture, enhancing the warm ambiance of the room.

4.76 out of 5 average rating, 173 reviews

Good Vibes Cozy Cottage on Million $ Row

Great location for this cottage one block from Infamous Bayshore Blvd. Smart Tv's and quiet back porch with fire pit makes this location perfect for vacationers. Short walk to Bayshore blvd with scenic views of downtown Tampa and beautiful Tampa Bay water ways. Come and enjoy biking, running, skating or just walking along this 4 miles continuous waterfront walkway. You will have views of Tampa Bay on one side and views of multi-million dollar homes on the other during your stroll.

Cottage in Central Oak Park

4.9 out of 5 average rating, 157 reviews

Adorable Cottage, Pet friendly, near beach & DT

The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.

4.99 out of 5 average rating, 279 reviews

The cottage exterior features a light teal facade with white trim and multiple windows allowing natural light. A welcoming front porch includes a central entry door flanked by two large windows. The address is displayed prominently above the door. Lush greenery surrounds the base of the structure.

Cottage in Gulfport

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

4.99 out of 5 average rating, 352 reviews

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street, short walk to waterfront. Private yard with grill. Enjoy curated décor and two king suites. Stroll to Dunedin's restaurants, breweries, shops, and live music. Enjoy stunning waterfront sunsets or drive minutes to award-winning beaches, Honeymoon Island and Clearwater Beach. Sleeps 6 comfortably with bonus twin sleeper spots and includes beach and kids’ gear for a seamless escape. Treat yourself and book this Dunedin guest favorite today.

Popular amenities for cottage rentals in St. Petersburg

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A spacious outdoor deck is shown, featuring a hot tub covered with a protective lid. Blue and white lounge chairs, along with bright cushions, are arranged for relaxation. The cottage's vibrant turquoise exterior is complemented by a cheerful yellow door and lush surrounding greenery.

4.96 out of 5 average rating, 194 reviews

Harbor Oasis | Hot Tub | Private | Lush Backyard

Cottage in Clearwater Beach

A charming duplex features a bright pink exterior with white awnings. A swing and patio chairs are located in the front yard, surrounded by potted plants. Bicycles are parked nearby, enhancing the inviting atmosphere of this beachside property.

4.78 out of 5 average rating, 156 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

Cottage in Clearwater Beach

A small private patio area is displayed, featuring two light-colored chairs positioned beside a sliding glass door. The patio is paved with antique bricks, and lush greenery surrounds the space, creating a cozy entrance to the cottage.

4.74 out of 5 average rating, 224 reviews

Lemon Cottage Steps from Beach

4.98 out of 5 average rating, 42 reviews

Beachy Keen Cottage A only steps to the Beach

The outdoor pool area features a clear water pool surrounded by lounge chairs and vibrant umbrellas. A bright blue building is visible in the background, complemented by colorful accents along the poolside. Lush greenery adds to the relaxed atmosphere.

4.91 out of 5 average rating, 128 reviews

Sunny - Key West Vibe Cottage - Pool - Walkable

A private hot tub is positioned on a wooden deck, outfitted with two black chairs and a small table. The cottage features a light blue exterior with a white door framed by two towels. A pergola with climbing plants is visible in the background.

4.91 out of 5 average rating, 100 reviews

Heart of Safety Harbor | Hot Tub | Luxe Comfort

Cottage in Clearwater Beach

The exterior view of a charming blue cottage is presented, featuring white accents and shutters. Two light-colored lounge chairs are positioned on the paved front area. Lush greenery surrounds the property, enhancing the inviting beach house vibe.

4.78 out of 5 average rating, 161 reviews

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

4.84 out of 5 average rating, 106 reviews

A charming coastal cottage is depicted, featuring a welcoming front porch with rocking chairs and vibrant seating. Lush plants in decorative pots frame the entrance. The exterior is painted in soft grey tones, complemented by white shutters and a serene pathway leading to the door.

Cottage in Crystal Beach

Happy Camper Cottage | Cozy Oasis with Hot Tub

Pet-friendly cottage rentals

4.81 out of 5 average rating, 72 reviews

A spacious living area features a light-colored couch and a coordinating armchair, positioned on a decorative area rug. A wooden TV stand holds a flat-screen television. Wall art adds color, while a ceiling fan provides comfort. Natural light filters through the windows.

Cottage in Largo

Cottage by the Coast 2 bd - Pet Friendly

4.91 out of 5 average rating, 124 reviews

A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.

Cottage in Ruskin

Little Manatee River Cottage

A single-story cottage features a pink exterior with large windows allowing natural light. A landscaped garden with decorative stones is visible in the front. White chairs are placed near the entrance, and ample parking spaces are provided in the driveway.

4.9 out of 5 average rating, 311 reviews

Vintage Florida Beach Cottage B

A cozy interior space features a neutral color palette with a striped bedspread. A serving tray holds two white cups beside a small dish of candy. Natural light fills the room, highlighting a kitchenette in the background, complemented by white cabinetry and a subtle decor.

4.86 out of 5 average rating, 373 reviews

Cozy up in a French Country nest NEAR EVERYTHING

A charming cottage exterior is highlighted by vibrant blue accents on the door and window frames. Lush palm trees surround the property, and a pathway of red bricks leads to the entrance. Gravel landscaping complements the home, enhancing its welcoming appearance.

4.7 out of 5 average rating, 218 reviews

Beachy Paradise

A spacious living area features a large sectional sofa in a neutral tone, accented by coastal-themed artwork on the walls. Light wood flooring complements the room, which includes a dining table and two bar stools, allowing for casual seating options. Bright natural light floods the space.

4.91 out of 5 average rating, 129 reviews

ALL NEW! Coral Sands II ~Coastal Modern 2/2 IRB

5 out of 5 average rating, 12 reviews

A cozy living area features a light gray sofa with decorative throw pillows, positioned across from a wooden coffee table. A modern artwork adorns the wall, and a flat-screen TV is mounted nearby. Natural light enters through a window, enhancing the calm atmosphere.

Cottage in Tampa

Cozy South Tampa Cottage Near Macdill AFB!

Cottage in St. Petersburg

A charming cottage exterior is framed by lush trees, with a front porch featuring a welcoming entry door. Decorative potted plants line the gravel pathway, enhancing the appeal of the space. A covered area is visible to the right, providing additional outdoor seating.

4.95 out of 5 average rating, 60 reviews

Old Florida Paradise Secret Lair Cottage

Private cottage rentals

4.91 out of 5 average rating, 32 reviews

A tranquil salt-water pool is framed by lush tropical foliage, offering a serene retreat. Sunlight filters through a striped awning, providing shaded seating areas. The circular pool is accompanied by a stone patio, creating a welcoming space for relaxation.

Cottage in Palm Harbor

Coral Cottage pool/firepit 2 bedr 2 bth sleeps 6

A welcoming outdoor space is highlighted by two red lounge chairs, adorned with floral cushions, positioned on a paved area. Lush greenery, including banana plants, frames the cottage-style villa, while a small seating area is visible in the background, providing a tranquil setting.

4.95 out of 5 average rating, 99 reviews

Adorable Villa 1 min to Downtown Dunedin

An open plan living area features a comfortable sectional sofa adorned with decorative pillows. A well-equipped kitchen showcases modern appliances and sleek cabinetry. Light floods in from a window, highlighting the serene coastal decor, including a framed palm tree photograph.

5 out of 5 average rating, 63 reviews

"Sweet Harbor Cottage" Walk to Downtown

4.93 out of 5 average rating, 14 reviews

A vibrant turquoise beach home is surrounded by lush green grass and a neatly landscaped yard, featuring a small palm tree. The front door, painted in a bold orange hue, is accented by a decorative welcome sign and colorful wall art.

Cottage in Largo

Beach Cottage October and November Openings!

A spacious sleeping area features a king-size bed with a light-colored bedspread. A ceiling fan hangs above, providing airflow. A comfortable chair is placed in the corner, and a kitchenette is visible in the background, equipped with modern appliances.

4.75 out of 5 average rating, 75 reviews

Tropical Coquina Cove Studio #1 5min Walk to Beach

4.77 out of 5 average rating, 39 reviews

A light-filled living area features a blend of comfortable seating, including a leather sofa and a recliner. A dining table is positioned near the sliding doors that lead to the deck, while a colorful area rug adds a vibrant touch underfoot.

Cottage in Sunset Beach

Coveted Sunset Beach Rental: Beautiful 2 Bdrm

A contemporary cottage is illuminated at night, showcasing large glass panels that reveal a warm interior. Surrounding the cottage, a manicured lawn features stone pathways and lush greenery, creating a serene outdoor environment.

5 out of 5 average rating, 57 reviews

Safety Harbor Cottage