Vacation rentals in Harbour Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Harbour Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in St. Petersburg

4.96 out of 5 average rating, 81 reviews

Breath taking views of sunsets and dolphins.

🏳️‍🌈Amazing views of the Boca Ciega and the pristine water of the Gulf of Mexico ,dolphins playing , beautiful palm trees , only 2 miles away from Madeira Beach,plenty restaurants nearby in walking distance cross the street from the famous Pinellas Trail 1 mile away from the marina to go fishing and rent a boat,You could go kayaking or you could go biking & youCould go fishing on the pier or go shopping!!Very clean place well-maintained very relaxing quiet best destination vacation in the area !!

Guest favorite

An outdoor dining area features a wooden table surrounded by four light-colored chairs. Lush green palm leaves frame the space, and decorative lanterns are placed on the table. A wooden privacy fence and colorful beach towels can be seen in the background, complementing a grassy area.

Home in St. Petersburg

4.93 out of 5 average rating, 40 reviews

King / Child Friendly / Near DT / Plunge Pool

Add us to your wishlist by clicking the ❤️ Unwind at our modern beach house near everything Gulfport & St Pete have to offer! Just over 1/2 mile away, head to dt Gulfport w/ its variety of restaurants, bars, breweries, coffee shops & boutiques. Gulfport's public beach is just a mile down the road, and other St Pete Beaches are a short car ride away. Don’t miss other nearby attractions like the St. Pete Pier and Dali Museum. This house is perfect for a couple's getaway or a fun family vacation!

Top guest favorite

Bungalow in Oldsmar

4.98 out of 5 average rating, 106 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Superhost

The image features a serene shoreline at sunset, with the sun casting a warm golden glow across the water. Silhouetted figures can be seen by the water's edge, surrounded by rocks and sandy beach. Gentle waves lap against the shore, creating a tranquil atmosphere.

Home in Holiday

4.93 out of 5 average rating, 14 reviews

Charming Sunshine Retreat

Welcome to our charming retreat in the heart of Florida! This cozy Airbnb is perfectly situated for your convenience, with easy access to shopping, dining, and all the amenities you could desire. Nestled just a stone's throw away from the stunning beaches that Florida is renowned for, you'll find yourself immersed in coastal bliss. Book your stay at our centrally located Florida retreat and discover the perfect balance between relaxation and excitement. Your dream vacation starts here!

Top guest favorite

A bright and airy dining area features a round wooden table surrounded by four light-toned chairs. A decorative centerpiece rests on the table, while large windows allow natural light to fill the space, blending seamlessly with the adjoining living room.

Home in Seminole

5 out of 5 average rating, 62 reviews

Coastal Getaway~Spacious~ 5 min to Madeira Beach!

Relax at our spacious, elegant, coastal getaway home and enjoy its proximity to the Top 25 Beaches in the US. Madeira Beach (2.3 miles), voted #9 and St. Pete Beach voted #1 (7.7 mi ) in 2021. Modern kitchen provides abundant space for meals and entertainment. Dine out or Door dash, we are centrally located near restaurants and shoppings area. FL Botanical Garden 5mi, Pinellas Bike Trail 1 mi. Walsingham, Lake Seminole, and Veterans Memorial parks all within 4 miles.

Guest favorite

A sandy beach stretches into the distance, adorned with scattered seashells and driftwood. Gentle waves roll onto the shore, under a cloudy sky. The horizon blends the sea and sky, creating a serene coastal atmosphere.

Condo in Madeira Beach

4.88 out of 5 average rating, 164 reviews

Awesome Madeira Beach Location Close To It all!!!

JUST ACROSS THE STREET FROM THE BEACH!!! Enjoy a great vacation stay in Madeira Beach! This is a 1 bedroom 1 bath condo, one floor, easily accessible unit. (One Queen Bed in bedroom, One pull out couch, one Queen murphy bed in living room). I have provided Beach Toys, Beach Cart, Coolers, Chairs Close to Beach Acess, Intercoastal Access, and lots of Restaurants and Bars. Johns Pass is less than a mile away. Madeira Beach is South of Clearwater and North of St Pete Beach

Guest favorite

Aerial view showcasing a sandy beach bordered by calm waters, with the coastline extending into the distance. Lush greenery can be seen alongside residential buildings, while the shoreline is dotted with beachgoers enjoying the sun.

Townhouse in St. Pete Beach

4.84 out of 5 average rating, 44 reviews

St Pete Beach @ Treasure Island #1 Beach in US 2BR

Voted 2024s #1 Beach in the USA!! Location location location. 3 minute walk to IntraCoastal waterway and 7 minute walk to Gulf of Mexico beaches (3minutes by bike.....provided). This 2BR 1BA condo is completely renovated and ready for your vacation getaway. Unique corner end unit has its own private patio. Rental also includes use of pool, 2 bicycles, 2 kayaks and tennis supplies (court right across street) and more. Short term rental permitted (3 night minimum).

Top guest favorite

Colorful kayaks are neatly arranged on the sandy beach near a thatched-roof pavilion. Sun loungers are visible in the distance, and calm water reflects the clear sky. Palm trees provide a touch of greenery, contributing to the serene coastal environment.

Townhouse in Ruskin

4.91 out of 5 average rating, 124 reviews

Ruskin Retreat

Our townhome is located in the beautiful Carribean style resort of Little Harbor. Resort amenities for you to enjoy are the large swimming pool and hot tub, basketball court, playground, private kayak launch, private beach (beach chairs and umbrella small fee), water toys for rent. Sunset Bar and Grill adjacent to beach and Hooks by pool , all within walking distance. Disney an hour and a half away and Tampa International Airport only 45 mins.

Guest favorite

A tidy outdoor area features charming green accents with a bright door leading to a unit. String lights create a soft illumination above a pathway lined with white stones and lush greenery, while a small table and chairs invite relaxation in the pleasant Florida climate.

Apartment in St. Pete Beach

4.8 out of 5 average rating, 314 reviews

Cactus Retreat | Walk to Beach <1mi | 4plex

🌵Fiesta Siesta – Where Every Day Feels Like a Party!🌴 Feed me tacos and tell me I’m pretty—because life’s too short for anything less! Welcome to Fiesta Siesta, a fun, vibrant escape just steps from Upham Beach in sunny St. Pete Beach. One of four uniquely themed units in a gated complex, this playful retreat is decked out in a vibey cactus theme that’s all about fiesta and siesta—because, why choose? Book now and let the fiesta begin! 🎉🌮

Superhost

An open living area features a gray sectional sofa facing a wooden coffee table. Bright artwork adorns the walls, complemented by stylish bar stools at the kitchen island. Modern fixtures and natural light create an inviting space, with light-colored flooring extending throughout.

Home in Pinellas Park

4.81 out of 5 average rating, 70 reviews

Beautiful Retreat Haven/ 7 miles to beach

Indulge in the perfect vacation getaway with our splendid 3-bedroom, 2-bathroom listing. This beautifully renovated property offers the allure of an outdoor fire pit, a recent brand new remodel, and the convenience of WiFi and smart TVs throughout the entire house. Nestled in a tranquil and quiet neighborhood, we're just 7 miles away from the sun-kissed beach, offering you the best of both worlds - peaceful relaxation and coastal adventure.

Top guest favorite

A serene beachscape is captured under a clear blue sky, featuring soft white sands that lead to gentle waves. The water transitions from light turquoise to deep blue. A few figures can be seen enjoying the shoreline in the distance, enhancing the peaceful atmosphere.

Apartment in Dunedin

4.98 out of 5 average rating, 240 reviews

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

Top guest favorite

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

Home in Palm Harbor

4.94 out of 5 average rating, 62 reviews

Private pool, Golf Cart, Completely Renovated!

Discover the ultimate retreat in a central location! Golf cart to Down town, restaurants, breweries, parks, and trails! Multiple beaches with-in a 10 minute drive. This thoughtfully equipped home is an oasis of leisure, offering a pool, games, and a fully-equipped kitchen. Optional Golf cart rentals, private boat rides and fishing trips add to the excitement. Book now for an unforgettable experience!