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.

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Guest favorite

Home in Palm Harbor

4.95 out of 5 average rating, 216 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.

Superhost

Home in Tampa

4.78 out of 5 average rating, 245 reviews

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

Experience True Old Florida! Papa’s Cozy, Rustic, Oceanfront Fishing Cabin. Brand new dock installed January 2024! 2 kayaks (individual rider), 2 bikes, & fishing rods provided. Traditional Old Florida style neighborhood, located 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. Central location to Tampa & beaches!

Guest favorite

Tiny home in Oldsmar

4.96 out of 5 average rating, 270 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 favorite

Guesthouse in Palm Harbor

4.96 out of 5 average rating, 258 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 shared pool and patio, 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.

Guest favorite

Rental unit in Clearwater

4.99 out of 5 average rating, 390 reviews

Private studio attached to house. Pool&bikes

Completely private A/C studio, bathroom & your own private saltwater pool. Studio attached to house. No cleaning fee. 1 block W to Edgewater trail. Beautiful sunsets on water. 1 block E to famous Pinellas trail. Stroll to downtown Dunedin or TD Stadium. Cruiser bikes provided. Drive, Uber, trolley or bike 4.5 miles to Clearwater Beach or Honeymoon Island. Near restaurants, shops, dancing, kayaking, fishing, boating, biking, baseball, etc! Space is not appropriate for under 18, pets, parties.

Guest favorite

Guesthouse in Clearwater

4.93 out of 5 average rating, 391 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 favorite

Tiny home in Clearwater

4.92 out of 5 average rating, 154 reviews

Tiny living

Keep it simple at this peaceful and centrally-located place that is 2 blocks from the water, only 2 blocks from Blue Jay stadium .6 mile in Dunedin. Our Luxury 2020 RV is top of the line and has privacy that is behind our enclosed gate with the entire unit fenced in for maximum privacy and also a great for you to relax and enjoy the outdoors. Unit has its own internet router with fast speeds for unstoppable internet action. We have available kids pen and high chair available upon request

Guest favorite

Tiny home in Dunedin

4.95 out of 5 average rating, 108 reviews

Cozy 1 bedroom tiny home with pool "Shelly"

Gorgeous newly built luxury tiny home in the heart of downtown Dunedin. This charming 1 bedroom 1 bath home is has everything you need for a perfect stay in our perfect little town. Only steps away from all the best restaurants, breweries, shops and activities in Dunedin. Dunedin was voted one of the best walking towns in America. Just a short drive to beaches including Honeymoon Island and Clearwater Beach. If you don’t feel like driving you can just relax in the pool.

Guest favorite

Hotel room in Dunedin

4.82 out of 5 average rating, 181 reviews

Seaside Artisan Apartment 4

This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s. There is no lobby for the guests, however we do list for rent the owner suit with front desk on airbnb as well. You can find it under “Seaside Artisan Motel Owner Suit”. This Airbnb is walking distance from the restaurants, shops and bars in Dunedin. It’s about 4 miles away from Honeymoon Island and about 6 miles from Clearwater Beach.

Guest favorite

Rental unit in Clearwater

4.94 out of 5 average rating, 198 reviews

Your own apartment, private with patio & driveway.

This Triplex apartment is centrally located in Clearwater near US Hwy 19 and Gulf to Bay Blvd (Rt 60). Clearwater Beach is a straight drive ahead (about 4 miles). This is a large 1 bedroom apartment that is perfect for two, but can also sleep four with the sleeper-sofa. There is a full sized, fully stocked kitchen, and a screened in patio in the back where smoking is allowed.

Guest favorite

Home in Palm Harbor

4.88 out of 5 average rating, 184 reviews

Cute Lil' House Near Historic Downtown Palm Harbor

They say that the best things come in small packages. Well that certainly rings true in this case. Our house may be small, but it is large on personality and full of elegant charm. Newly remodeled and filled with personal touches, this small package is ready to be your Florida retreat. Enjoy charming palm harbor on our golf cart for a small rental fee.

Guest favorite

Home in Clearwater

4.96 out of 5 average rating, 357 reviews

Coastal Cottage E - 1318 - Bikes and Beach items!

This guest house has been fully remodeled with brand new mini split-air conditioners. It shares a parking lot, grill, and laundry with other units. Included with this unit are 4 beach cruiser bikes, beach chairs, beach towels, umbrellas, coolers beach bag, bag of sand toys, beach cart, and more! Note: sorry no animals 💕🙏