Beach house holiday rentals in Longboat Key

This Airbnb exceeded every expectation! The property was beautiful, spotless, and incredibly well-maintained. The pool was a highlight—clean, peaceful, and the perfect spot to relax every day. The host was friendly, responsive, and made sure we had everything we needed for a comfortable stay.

The listing says it is just a few steps from the beach and that is true! It was so easy to go back and forth and with 4 kids and beach items that was very important. The house was beautiful and spotless. We felt right at home and we loved every second of our stay! Thanks Mark for helping us make a special family vacation!

My family had a wonderful vacation at Danielle 's house. It was everything and more than we expected. The house is beautifuly appointed with all you would need to thoroughly enjoy your stay. The kitchen is loaded with everything you could ever want to cook any meal. It is spacious & inviting for the family to gather together while we cooked. The house itself is majestic. The great room when you 1st walk in is so incredible. The house is inviting and makes you feel right at home. The beds are incredibly comfortable, bathrooms are big & roomy and the showers... oh my, full body shower heads make taking a shower a luxury. The lenai with the pool and hot tub is the perfect gathering place and oh so nice to take a swim after a long day at the beach. The dock out back is perfect for a morning coffee or evening beverage. We rented a kayak for the week & had a blast paddling out to the sound. The beach is private & so nice to enjoy the day at. Thank you Danielle for our great memories.

The rental was very clean and had everything we needed. Kitchen was well equipped and the grill was a plus! Our toddler loved the pool and all the beach toys! We enjoyed the location and quick access to the beach and restaurants. Will definitely consider staying again!

10 of us stayed at Jeff and Ingrid’s and it was perfect! The house was beautiful, plenty of linens and kitchen necessities. The location was great for walking to shops or beach! Loved the outdoor area! Perfect to unwind after the beach or dinner. We will be back!

Our stay at Casa Bonita was truly a five star experience. The location was great, just steps from the beach access crossing and bridge street where we enjoyed, shops, dining and drinks. No ubers needed! The actual space itself exceeded our expectations. There is plenty of space for lounging inside and out. The pool area offered shading and full sun areas, with games and a bathroom/shower located outside for easy rinsing off. The garage had everything we needed for the perfect beach trip including towels, floats and a wagon. Kitchen and bedrooms were very clean with all of the essentials. And our host Kelly was very responsive with anything we needed. We will certainly be back to Casa Bonita!

Can’t say enough about the place. Clean, peaceful walkable to bayside beach down the street, 5 minutes from great restaurants. Very responsive to our questions. Brought our golden doodle who feel in love with the expanse back area to run and play. Very high end appliances. Water views everywhere. We will be back!

I absolutely loved this peaceful, pristine and beautiful vacation home on Anna Maria Island. It is centrally located amongst turquoise beaches, delicious local food, fun gift shops and fully stocked grocery stores. The home itself was very clean, well maintained and beautifully decorated, both inside and outside. The living room was comfy, and had a lovely view of the front yard. The kitchen was the perfect size and the refrigerator was huge! The master bedroom was cozy and the bed very comfortable. The bathroom was very clean and the shower quite large. I also loved that there was a washer and dryer attached to the master bedroom. The outside was just as gorgeous as the inside. The palm trees, and numerous plants really added to the whole oasis feel, and added a layer of seclusion and privacy. I loved the fact that there was an outdoor shower and the dip pool was such a great bonus! The hosts checked in regularly and were very responsive. I would absolutely recommend this home!

We had an amazing week at Michael and Denzel’s home! It was actually better than the pictures with enough space for everyone to feel right at home. The layout was perfect for two families. The home is spotless and extremely well stocked. The island is beautiful and we enjoyed the pool everyday! Highly recommend this home. It will exceed your expectations in every way!

Excellent accommodations super close to the beach and many places to eat. The home felt like a second home with all needs met. The backyard was an oasis and the pool was delightful! The host was quick to respond and I would highly recommend.

We had a wonderful stay at this beautiful home. This home is super clean, well styled, and spacious. The backyard oasis is amazing - very private and quiet. The location is great; the home is close to all amenities as well as the beach. Communication with the host was exceptional. Dana is super responsive and very friendly and accommodating. I highly recommend booking this home!

We had a great time. Super clean, beautiful home, full of extras. The property has many things to do and keep everyone entertained. Great communication, definitely one of our favorite vacation homes. Can’t wait to stay here again!!!

Rebecca’s place was perfect for our family vacation of two young children, two parents and two grandparents. Her house sits on a dead end street just a few blocks from the beach. We found everything we needed for a few meals at home, and having a washer and dryer was convenient. The kicker was the outdoor pool, which we loved. We would easily recommend her place to anyone who wants a beautiful place to spend vacation.

Absolutely pristine place, the house is amazing, location is perfect and loaded with everything you need. Great host as well , we would love to come back to this place.

Pepper Tree exceeded our expectations! We have a 6 month old grandson and the proximity to the beach was delightful and the covered pool allowed us to utilize it throughout the day! The home was cozy and beautifully appointed! We loved our stay there and will DEFINITELY come back!! ❤️

I recommend this oasis it’s beautiful just like the pictures private the outside is breathtaking I was surprised on how many cool electronics was around the house from the bathroom to the oven lol but 10/10 I had a blast great way to start my 30s 🙏🏾

Had a wonderful time here! The property was exactly as described and Matthew was always available & communicative, should we have needed anything. You truly can't beat this location! Close to everything you'll need for short trips or long ones. If you're thinking of staying here, DO IT!

Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!

Adorable. Cutest little house on the block. Location was perfect and walkable to everything. Quiet and safe while still being downtown. Check in was easy and parking right next to the home was so nice.

Bettina has a lovely home and it’s close to all beaches. The neighborhood is peaceful and quiet! Very relaxing. Bettina is proactive, friendly and very responsive. She made check in and check out very easy and is always asking for help. I can see why she’s a super host! I would recommend for a peaceful getaway close to the beaches.

Beautiful home and surrounding area, Pristine home in brand new condition. Expertly furnished, lots to do for teenagers, they loved the ice bath! Well stocked kitchen. The host was very responsive and helpful would definitely recommend this location and home. Happy vacationing.

Stayed here for the national rowing competition for one week. The place is lovely - very clean, the complex is nice & the pool is great. It was a perfect location for us - halfway between the race course where we needed to be every day and close to downtown. The beach wasn’t far either and I liked the location and the complex very much. We felt safe and it was pretty quiet and peaceful. The owner is responsive and detail oriented with how to check in, get into the unit, etc. I would stay here again.

We loved our stay at the Sandy Toes villa and hope to return some day. The location was fantastic, private and quiet but very close to the beach, restaurants, shops and tennis/pickleball courts. The villa was very clean and well maintained. Marlanea was very responsive and helpful.

Had an amazing time staying at the mango! It was the perfect private spot about 10 minutes from the beach that couldn’t have been any better for my husband and I. We did have a slight AC problem during the middle of the week but Whitney responded so quickly and was able to get it fixed so fast while we enjoyed our day at the beach.