We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Highland Lakes, Clearwater

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Highland Lakes, Clearwater

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

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Home in Tampa

4.78 out of 5 average rating, 232 reviews

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

Papa’s Cozy, Rustic, Oceanfront Fishing Cabin. Brand new dock installed January 2024! 2 kayaks, 2 bikes, & fishing rods provided. Old Florida style neighborhood near charming Oldsmar on a Saltwater Gulf canal, only a few houses down from open bay. Great for the outdoorsy vacationer. The depth of the canal moves up and down with the tides. It’s usually shallow but has many fish in high tide. Proudly dog friendly! Not suited for everyone. If you’re looking for luxury this is not the place for you!

Home in Palm Harbor

4.94 out of 5 average rating, 188 reviews

Well Appointed 100% Private Suite/Lake View

Private entrance/ Private suite/bath w/ walk in closet. Microwave/fridge. Convenient parking. Beautiful view of the lake and all its wildlife. Everything you need to go to the beach is in the room, beach towels, umbrellas, beach mat. Due to host allergies, NO pets/animals/service animals. No smoking/vaping/drinking/drunkenness. Sensitivities? I do not use plug-ins, scented sprays, scented detergents/dryer sheets. If traveling w/ a service animal, kindly, please choose another Airbnb property.

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 210 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Tiny home in Oldsmar

4.96 out of 5 average rating, 252 reviews

Louisa's Cottage

This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants ,This Private1BD/1BA Cottage is split down the middle you have your own entrance And private space to yourself. Don’s place is on your left and Louisa’s cottage is on your right side.This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.

Guest suite in Dunedin

4.93 out of 5 average rating, 210 reviews

Downtown Coastal Studio, 10 min. to the beach!

The studio has a bright and airy atmosphere, clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin in walking distance to the Pinellas Trail and Main St. Simply park your car and enjoy town on foot or rent a bike and cruise around. We are close to Honeymoon Island and Clearwater Beach (ranked in the top 15 white sand beaches in the world), the marina, a park just across the street with a nice path to stroll along the water or take in the sunset.

Guesthouse in Clearwater

4.94 out of 5 average rating, 374 reviews

Magical Garden Paradise: Hunt Haven Hideaway.

In the heart of Clearwater, a peaceful artists' retreat that will remind you of TN or North Carolina. If you like nature, this is the spot for you! Wander through the "Florida natural" garden and find spots for relaxation or conversation. If you like baseball, we are close to two SPRING TRAINING stadiums and 25 minutes from Raymond James Stadium. About 20 minutes from the beach, if you prefer fun in the sun. Safe, clean gated property centrally located for shopping and activities.

Guest suite in Dunedin

4.98 out of 5 average rating, 173 reviews

Dunedin Suite East, 15 minutes to local beaches

Dunedin Suite East is modern and spacious with a full kitchen and private patio area out back. You will find it clean, comfortable, and convenient staying here. The suite is a 15 minute drive to Honeymoon Island and Clearwater Beach, ranked some of the nicest beaches in the world. Beach supplies are included. You can rent bikes and bike the Pinellas Trail. The Pinellas Trail, Blue Jays Stadium and Main St with tons of restaurants, breweries, art, and shops are all in walking distance.

Apartment in Safety Harbor

4.92 out of 5 average rating, 170 reviews

The Downtown Studio

Featured in the Hallmark movie "Love in the Sun", The Downtown Studio apartment is on the second floor of the original Safety Harbor Hotel on Main Street, built in 1914. The flat features all the comforts of home. The Inn is right in the center of downtown Safety Harbor, 15 minutes from both Clearwater (PIE) and Tampa International Airport (TPA) , 10 miles to the white sandy beaches of Clearwater, 17 miles to St.Petersburg. This is a perfect home base for your Gulf adventures.

Apartment in Dunedin

4.95 out of 5 average rating, 190 reviews

The Coastal Retreat

Studio apartment. Light airy Coastal Eclectic décor. Walk in closet, full size bath, Fully equipped kitchen . Key west style tropical courtyard with fish pond. Off street parking . Gas grill and outdoor dining area. One block off the Pinellas Bike trail, walking/biking to historic downtown Dunedin, Toronto Blue Jays spring training. Minutes to the 3 of the country's best beaches! Clearwater Beach, Honeymoon Island, and Caladesi Island.

Bungalow in Dunedin

4.89 out of 5 average rating, 189 reviews

Cozy Park Model RV with Sun Room. No pets

A relaxing space great for beach lovers, cyclist , and people who love the outdoors. Close to beaches restaurants and historic Downtown Dunedin. Located in the Dunedin RV Resort . Honeymoon Island State Park is 3 miles, Clearwater Beach is about 9 miles. Jolly Trolley goes to Clearwater Beach St Petersburg , Tarpon Springs where the sponge docks are. Greek Food and pastries are amazing in Tarpon Springs. NO PETS

Apartment in Dunedin

4.98 out of 5 average rating, 214 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

Apartment in Dunedin

4.93 out of 5 average rating, 114 reviews

Summer Sale! Nice Studio apt- Downtown Dunedin!

Come relax in this beautiful Studio apartment. Close to everything! One block off of The Historic Main Street of Downtown Dunedin. Tons of restaurants, shops, parks and activities super close-by. World Famous Beaches near-by. Whether your traveling for work or fun, there are Lots of fun things to keep you entertained! Great for traveling healthcare workers- ONE block away from the Mease Dunedin Hospital!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Highland Lakes, Clearwater vacation rentals

Free parking on premises

Air conditioning

Stay near Highland Lakes, Clearwater's top sights

Ruth Eckerd Hall45 locals recommend

Crest Lake Park16 locals recommend

Eagle Lake Park18 locals recommend

Clearwater Threshers36 locals recommend

Congo River Golf25 locals recommend

Celebration Station27 locals recommend

Other great vacation rentals in Highland Lakes, Clearwater

Home in Dunedin

4.98 out of 5 average rating, 118 reviews

Downtown Dunedin Bike Trail and Beach

Apartment in Dunedin

4.95 out of 5 average rating, 171 reviews

Mermaid cottage

Townhouse in Palm Harbor

4.96 out of 5 average rating, 112 reviews

Water view-Close to Trail & Gulf-Bikes, beach gear

Guesthouse in Clearwater

5.0 out of 5 average rating, 27 reviews

Cozy In-Law Suite Near Beach

Apartment in Clearwater

5.0 out of 5 average rating, 52 reviews

Welcome to your cozy studio!

Home in Oldsmar

4.86 out of 5 average rating, 71 reviews

Private In-Law Suite with Beautiful Bay View

Guesthouse in Dunedin

4.84 out of 5 average rating, 64 reviews

Guest House in prime location!

Home in Dunedin

5.0 out of 5 average rating, 25 reviews

Downtown Dunedin Bungalow Includes Bikes

Destinations to explore

Monthly Rentals Highland Lakes