Vacation rentals in Harbour Island

A screened-in patio features a round table with two striped chairs, overlooking a pool illuminated by soft blue lighting. The surrounding area is tiled, and the pool creates a welcoming ambiance, inviting relaxation and enjoyment during evening hours.

4.95 out of 5 average rating, 64 reviews

5 Beds/3 Beautiful Bedrooms /2 Bath/Pool Paradise!

StephenieRating, 5 stars6 months ago

Marueen is a 11/10 host! Working with us with Helene's passage near Florida and even after. she was extremely responsive during the process and continued to check in even after. the pool was wonderful way to relax, and the couch was the perfect place to decompress after all the stress. I would recommend this listing to everyone and anyone looking for the perfect, peaceful getaway!

A refreshing pool area is featured, complete with inflatable toys and sun loungers adorned with striped towels. A spacious patio includes a BBQ grill and an outdoor dining space, shaded by a large umbrella, providing a comfortable setting for relaxation.

5 out of 5 average rating, 19 reviews

5BR Villa w/ Pool + BBQ | SoHo & Downtown Tampa

JustineRating, 5 stars2 weeks ago

Absolteuly loved our time at Nish & Ash's. It is clean, spacious, unreal outdoor area! Our favorite part of staying here was breakfast and dinner in the patio area! Nish & Ash do everything to make your stay comfortable! The location is perfect-close to everything! Would come back here in a flash!

A private hot tub area is illuminated with soft blue LED lights, creating a calming ambiance. The space features a sleek, covered hot tub, surrounded by wooden decking and lush greenery, ensuring a tranquil retreat.

5 out of 5 average rating, 185 reviews

Multi-Award Winning & Top 5% Rated on Airbnb

AnnaRating, 5 stars5 days ago

This place is truly special. The location is right in the middle of everywhere we wanted to go. Easy to find, park, and get into. From the moment we arrived, Jason and Neil were the most gracious hosts. And the property is amazing! Every single thing has been carefully thought out and decorated for style and comfort both inside and out. So much so that we spent the last day on property just enjoying the peace and quiet. I almost don’t want to say anything because I don’t want to share this find, but the place (and hosts) are too amazing not to get all the love they deserve. Can’t wait to come back.

The image depicts a serene lakeside scene featuring private docks leading to calm waters. Lush green grass frames the area, complemented by tall reeds and trees. A kayak is visible on the dock, and soft clouds drift across a bright blue sky.

4.93 out of 5 average rating, 59 reviews

Waterfront Pool Home & Nature Lover's Paradise

DavidRating, 5 stars3 months ago

Place was great for what we needed. Easy access to the casino and only 10 to 15 minutes to Busch Gardens. Eric was great and helped with any questions we had. The home had everything we needed to enjoy our stay. Thanks for having us!

4.95 out of 5 average rating, 41 reviews

A serene sleeping area features a spacious bed with a light green quilt. Natural wood paneling creates a warm ambiance, while large windows bring in views of the lakeside. Soft curtains frame the windows, enhancing the connection with the outdoors.

Villa in Thonotosassa

Lakeside Villa

AviRating, 5 stars2 weeks ago

This was not only an incredible house, but Kyle was also an amazing host. He was extremely responsive and genuinely cared about our stay. We can’t stop raving about how lovely this place was—gorgeous views, cozy cabin vibes, peaceful, and private. We’d definitely come back.

5 out of 5 average rating, 11 reviews

Home in Riverview

Tampa Paradise For All Occasions

KathrynRating, 5 stars1 month ago

House was plenty big enough our family enjoyed the pool also one thing was the washer smelled so we were not able to do laundry . I know if I would have contacted Dana about it she would have come over and fixed it but we just didn’t have time. Thank you for letting us stay in your home. We will definitely stay here again!

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What guests are saying

Waterfront 2 Bedroom Condo Amazing SunsetsPool

4.92 out of 5 average rating, 78 reviews3 weeks ago

Our family had a wonderful time at this condo! We enjoyed waking to see the ocean every day and also had enough space to relax on our vacation. Helena provides a beach bag with towels and sand toys that were a very nice touch for our beach day. The staff at the bar/restaurant were great and we also felt safe with the 24 hour security guards on duty. This place really made our trip extra special!

Condo in Tampa

What guests are saying

An outstanding place to stay!

4.94 out of 5 average rating, 18 reviews1 month ago

I stayed at Karina's lovely 3-bedroom house 2/15/25-3/15/25. The place was clean, comfortable, and well-supplied. The pool was great. I was in there a lot. The temperature was about 73 degrees. The beach is about 1 hour away (due to traffic). There were many restaurants, grocery stores, LA Fitness, and anything else you might need nearby. If you like dive bars - go to Joy Bar. It has 2 pool tables, 2 dart boards, and cheap drinks. Karina communicated well and promptly. I would absolutely stay here again.

Home in Tampa

What guests are saying

b&b cabin rentals

4.87 out of 5 average rating, 15 reviews3 days ago

A great little hideaway in a convenient location right by the interstate. The home was exactly like it was shown in the pictures. It was clean and prepared for our arrival. Adam was responsive and helpful with providing a map to the cabin through the park, it would have been difficult to find without that, so thank you Adam! I would stay here again for sure the next time I’m in the area!

Cabin in Dover

What guests are saying

The memories house

4.92 out of 5 average rating, 24 reviews1 month ago

What can I say? Well Katiuska’s place turned out to be pretty much spot on. It was a fantastic little 2-night getaway to watch the Phillies play one more time during their St. Patty’s Day game, which they won to boot! The living room TV was fantastic & the Roku app never missed a beat. We’d definitely stay there again, as the few neighbors we met were very friendly indeed.

Home in Tampa

What guests are saying

Relax at Renellie

5 out of 5 average rating, 27 reviews3 months ago

Christopher was great we had some electrical issues and he was very responsive and willing to accommodate our needs. This home is small but has lots of spaces to lounge and relax or read a book. The backyard was great we had a small reunion with family and it really accommodated our needs. The bathroom could use a lock for the door and some tighting up of the bowl but otherwise we were very happy with our stay.

Home in Tampa

What guests are saying

Amazing Private Beach Home

4.92 out of 5 average rating, 49 reviews1 week ago

This place was absolutely perfect. The private beach was the highlight — quiet, clean, and just steps from the property. It felt like our own little slice of paradise. The home itself was spotless and beautifully decorated, with everything we needed for a comfortable stay. The host was super responsive and thoughtful, even leaving some local treats for us when we arrived. Whether you’re looking to relax by the water or explore the area, this spot has it all. We’re already planning our next trip back!

Home in Oldsmar

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Popular amenities for Harbour Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Harbour Island

4.91 out of 5 average rating, 32 reviews

A clear blue heated pool is surrounded by a spacious patio with stone pavers. Large glass doors provide a view of the lush greenery beyond, while the exterior walls are painted in a soft gray hue, complemented by natural light filtering through.

Home in Oldsmar

Exquisite Fun Getaway with Private Pool!

KellyRating, 5 stars1 week ago

This place is amazing! even better than the pictures. we’re definitely gonna book it again

Superhost

The exterior of the house features a two-story design with large windows allowing for natural light. Soft outdoor lighting highlights the entrance, while a neatly landscaped yard with palm trees creates an inviting atmosphere. The driveway leads to a two-car garage.

Home in Riverview

4.9 out of 5 average rating, 72 reviews

2 Story comfort beautiful home with all amenities

JamesRating, 5 stars2 months ago

I had an incredible experience at this Airbnb! The home had everything I needed for a comfortable stay. The location was perfect—peaceful yet close to everything I needed. I would absolutely stay here again and highly recommend it to anyone looking for a top-notch Airbnb experience. Thank you Edgar!

A modern kitchen is showcased with white cabinetry and a spacious granite countertop. Stainless steel appliances reflect light, while large windows bring in natural light. The marble-like tile flooring adds elegance, and a potted plant provides a touch of greenery.

5 out of 5 average rating, 16 reviews

Poolside Paradise with Basketball Court

SkylarRating, 5 stars1 week ago

5 stars! Everything about our stay was absolutely perfect. The host was incredibly accommodating and thoughtful—they truly thought of everything to make the space feel just like home. From the moment we walked in, we felt welcomed and cared for. The beds were incredibly comfortable—we slept so well each night, which is such a rare find when traveling! They didn’t miss a single detail. Every little thing we could’ve needed was already there, making our stay effortless and relaxing. You can tell they genuinely care about their guests’ comfort and experience. On top of it all, they were beyond kind and so responsive to any questions we had. We 100% recommend this place to anyone looking for a cozy, well-cared-for stay—and we will absolutely be back! Love how they are transforming this area and the love and energy they are pouring into all the surrounding homes. Oh, and the noise level at night… NONE which was very important to us. Love this place!

4.91 out of 5 average rating, 137 reviews

Loft in Tampa

Vacation Getaway 1

ImannyRating, 5 stars5 days ago

Very much about they guests had a wonderful stay!💕

Superhost

A modern kitchen features sleek white cabinetry and a spacious island with seating for four. Stainless steel appliances, including a refrigerator and oven, are visible. Natural light floods the space through large windows, enhancing the open layout that connects to a dining area.

Home in Apollo Beach

4.88 out of 5 average rating, 17 reviews

Waterfront Retreat

MargaretRating, 5 stars2 weeks ago

House was so beautiful and very clean. Sabrina was so great. I really appreciated her flexibility to allow us to check out a little later. Upscale furnishings and very well maintained property. I would definitely stay again. The outside area and pool was beautiful. The only con was the pool was not heated so some of us could not use it, I really tried but it was just too cold, even though the temp outside was in the high 80's the pool had not acclimated yet. But overall we really had wonderful family time :) Thank you so much Sabrina!

4.89 out of 5 average rating, 9 reviews

Bring your family and friends to our luxury airbnb

AprilRating, 5 stars1 week ago

I was in town celebrating my 45th birthday with family, and this home was the perfect accommodation. We enjoyed the jacuzzi and pool the most! The home was clean, warm and inviting. Our host Leon was quickly responsive and extremely accommodating...he was able to grant us a last minute late check out, which we greatly appreciated. We'd definitely stay again if we ever find ourselves back in Tampa.