House vacation rentals in Longboat Key

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Popular amenities for Longboat Key house rentals

House rentals with a pool

Guest favorite

Home in Bradenton Beach

4.94 out of 5 average rating, 33 reviews

Beach Bliss! Short stay specials! Walk to beach!

RachelRating, 5 stars1 month ago
What a perfect place!!! But we unfortunately, were part of the mandatory evacuation due to Hurricane Helene. However, the two full days we had were great! The pool is great, easy walk to the beach, plus tons of beach chairs, toys, umbrellas, etc. Upon checking in there was a bathroom that hadn’t been cleaned, but it’s hard to find due to the door. Within minutes Amanda responded to my message and then 20 minutes later the cleaning crew was there to clean the bathroom and it as spotless. They were also super apologetic. Additionally, Amanda was fantastic during all the questions we had with the hurricane approaching and the evacuation. Unfortunately, we were unable to return due to the damage and Amanda issued 50% of our refund. We sincerely hope to return to this rental and be able to enjoy it the entire length of our stay next time (just not during hurricane season).
Guest favorite

Home in Anna Maria

5 out of 5 average rating, 22 reviews

Veselka - Canal front w private heated pool & dock

JulieRating, 5 stars2 months ago
We had such a fantastic stay, and Michael & Denzil were wonderful hosts. The house was just as it’s reflected in the photos, and was well stocked. We especially enjoyed the pool as well as the dock. Our boat captain was able to pick us up in our backyard, which was super convenient and allowed us to spend some time out on the water. We rented a golf cart that came in really handy for exploring, running to the corner store, and catching sunsets at Bean Point. We had an issue with the A/C during our stay, but Michael and Denzil were super responsive and had it fixed in hardly no time. A wonderful stay, wonderful hosts, and I highly recommend this lovely home. Hope to be back next year!
Guest favorite

Home in Holmes Beach

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

SeanRating, 5 stars1 month ago
We just wrapped up a very nice one week vacation and stay. Kathleen and her husband were incredibly flexible at both check-in and check-out and they went above and beyond to help us. Throughout the trip Kathleen and her husband were very communicative and they came to the property onsite several times to assist with a few small property challenges that came up which were out of their control. The pool and patio area is the highlight of their property. It is so peaceful and cozy and the pool was the perfect temperature and very well maintained. The second highlight of their place is the kitchen which is by far the best stocked kitchen at an Airbnb we have ever experienced. Third, we very much appreciated the abundance of beach gear and baby/kid gear they have onsite. The setup of the house is slightly non-traditional with some sliding doors to shut rooms off but overall we had a great stay. 5-7 minute walk to beach is accurate. Beds were very comfy.
Guest favorite

Home in Bradenton

5 out of 5 average rating, 117 reviews

No Storm Damage! We Have Power!HeatedPool.Firepit!

MichaelRating, 5 stars2 weeks ago
The stay we had at this home was amazing. My kids loved all the games available and of course the pool. The outdoor theater was awesome to have as well. The home is beautiful and had plenty of space for our family of 8 to spread out. The kitchen is well stocked with everything you will need. The master bath is amazing. We go to Florida twice a year and by far this house has been the best. You will not be disappointed with this home. Julie was also very responsive when needed and very nice. My kids can’t wait to go back to this house. We will definitely be booking again.
Guest favorite

Home in Sarasota

4.88 out of 5 average rating, 145 reviews

5 minutes to private Siesta Key Beach + 2 pools

TimRating, 5 stars1 month ago
We had a great, albeit brief stay at Solen's place. The day we checked in we arrived later than expected, around 11:30p, and the following day I met Sinan and then our family spent the day at the beach. Solen and Sinan's place was a perfect size for our little family, and when we arrived the pack and play crib was already set up and ready for our sleeping child. We appreciated all of the kids equipment being ready at our disposal for a beach vacation, including the kids dishes, highchair and a baggie of outlet covers! Minimum booking time was 6 nights, however our vacation got cut very short by Hurricane Helene. When we had to up and leave so quickly on the 3rd day of our stay Solen and Sinan's response was to keep our family safe, they even took proactive steps to refund the nights we did not get to stay. We will absolutely book again in the future, the home was perfect and the beach was dreamy.
Guest favorite

Home in Holmes Beach

4.95 out of 5 average rating, 94 reviews

The Peachy Beach House, steps to the gulf

ChrisRating, 5 stars2 months ago
The house was wonderful. We rotated between the beach (5 minute walk) and the backyard pool all week. There are many wonderful restaurants within a 10 minute golf cart ride. Frances was quick to respond anytime we had a question. We loved the house and the overall experience on the island. We’ll be back and will definitely book with Frances.
Guest favorite

Home in Lido Key

5 out of 5 average rating, 15 reviews

Walk to Lido Beach &St. Armands -grill/HEATED POOL

MariaRating, 5 stars2 months ago
My husband and I had a wonderful stay at Lori's place... it's like a tropical getaway.. so relaxing and private. The beach is one block away and having the use of the trolley, umbrellas and chairs was super..... St Armand's Circle, a short walk away, is just lovely with lots of nice places to eat, to have a drink or an ice cream. The area is just beautiful and I'm already longing to feel the Lido Beach silky smooth sand beneath my feet again, we'll be back soon! Thanks for everything Lori and Sandy.
Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 68 reviews

The Wisteria Oasis W/ heated pool & hot tub

LjubisaRating, 5 stars1 week ago
The location was great, on a small quiet street. The driveway is on an incline so a low car might not make it up without scratching the front end. The hot tub was ready, lights by the pool with a great vibe. Swings for the kids and a hammock to relax in. There was a tree that was leaving a lot of leaves in the pool and patio but it was a very quiet and peaceful. Great time and not far from downtown.

Weekly house rentals

Guest favorite

Home in Holmes Beach

4.94 out of 5 average rating, 89 reviews

Breezy Harbor AMI pool retreat near the Beach

ChristyRating, 5 stars1 month ago
We weren’t able to stay due to a Hurricane but I wanted to highlight Mario’s excellent communication leading up to our trip! Thank you! We will definitely book another trip in the spring!
Guest favorite

Home in Anna Maria

5 out of 5 average rating, 31 reviews

Paradise Blu by Beach Boutique Rentals

GabrielRating, 5 stars1 month ago
Truly one of the best properties, if not the best we have been to, not only in Anna Maria, but in the entire country. It was clean, beautiful, well decorated, amazing backyard, plenty of entertainment within the property, and amazing location close to an amazing beach. If you are looking for an amazing stay, don’t book anywhere else but this property. It is truly worth it. We will definitely be back soon!
Guest favorite

Home in Sarasota

4.91 out of 5 average rating, 81 reviews

Tangerine House | Sauna | Near Downtown

YveRating, 5 stars1 month ago
This was one of my favorite AirBnbs and I’ve stayed in many! Susan’s space felt like home. Every single item you’d find in a home was there. A record player, games, books, a cook book, a huge tub, even bath bombs, not to mention a sauna. Overall a beautiful, comfortable home and so clean. So many bnbs use glade plug ins (which aren’t healthy) but this space smelled like literally a breath of fresh air. Every thing was addressed and the location was top notch, just 5 minutes from downtown and 15 from Sarasota beach. Highly recommend!
Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 54 reviews

St Armand's Mid-Century Oasis

BrittneyRating, 5 stars1 month ago
Such a nice home in a perfect location. Walking distance to many shops and restaurants and around the corner from the beach and center to anything else you may want to see. Pool and floaties were so nice. Beach chairs available. Had to adjust reservation unexpectedly due to a hurricane but host was accommodating and very responsive our entire stay. Also, loved that it wasn’t smelly! The entire house was squeaky clean without any need for overpowering scents and air fresheners. If you’re traveling with a family with little ones, keep in mind that the house isn’t rambunctious kid friendly (and it’s not meant to be). So do a quick run through and move up the breakables low to the ground when you check in but no biggie. Def stay here if you can!! We’ll be coming back for sure.
Guest favorite

Home in Holmes Beach

5 out of 5 average rating, 45 reviews

Luxury Home Steps to Quiet Beach on 78th St

BrittanyRating, 5 stars2 months ago
This beach house was perfect! We loved the location and amenities of this home. Minh was an amazing host. We stayed during a tropical storm and she was very generous to our family and kept checking in with us. Her house stayed safe, dry, and on a road that doesn’t flood! The week cleared up and we had a great stay. We loved the cleanliness, the location and the extra beach items and bikes. We walked to the beach every night for the sunset. I would definitely recommend this home and location.
Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 49 reviews

The Mango House Beach Cottage

SarahRating, 5 stars2 weeks ago
Just as described. Private yet accessible. Host was responsive and reasonable.
Guest favorite

Home in Indian Beach-Sapphire Shores

4.95 out of 5 average rating, 42 reviews

Large and Beautiful, Steps from Bay, Ringling!!

ChristinaRating, 5 stars3 weeks ago
Although we were unable to stay at the Airbnb due to Hurricane Milton I just wanted to take the opportunity to leave Oren a spectacular review with his much appreciated communication with us and understanding of not being able to attend our reservation. We do hope in the future we can come down and stay at Oren’s location as it looked wonderful.
Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 56 reviews

Lovely Home by Sarasota Bay

RandyRating, 5 stars5 days ago
nice place enjoyed our stay

Private house rentals

Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 52 reviews

Sun-filled cottage with pool, walk to beach

ØyvindRating, 5 stars2 months ago
The house is a perfect spot for a beach vacation! It had everything we wanted and needed. Short walk (1 km) to the beach, and the heated pool was awesome! The house had everything we needed such as beach trolley, chairs, beach umbrella and much more. First AirBnB that have a complete supply of kitchen stuff to prepare all food in the house! One of the best houses we have ever rented!
Guest favorite

Home in Sarasota

4.89 out of 5 average rating, 75 reviews

Entire Comfy Sarasota Home Mins to Beach+Downtown

ErichRating, 5 stars1 month ago
Location was amazing and very close to everything, quiet neighborhood and friendly neighbors. Overall great experience. Would highly recommend and we'll use again.
Guest favorite

Home in Anna Maria

5 out of 5 average rating, 22 reviews

༄ Sunset Shore on Anna Maria Island ༄

SuzanneRating, 5 stars2 months ago
The home is very welcoming and nicely decorated. Pool and landscaping is beautiful and back deck with grill was perfect. We did have an issue with the pool but Jeff was VERY responsive and on top of getting the issue fixed, and the the problem was rectified the next morning as promised. Thank you!! Access to the beach a block and a half away was probably one of the most convenient beach accesses we saw there. Anything you could want/need for the beach and pool was available. Would definitely stay again when visiting Anna Maria Island
Guest favorite

Home in Holmes Beach

5 out of 5 average rating, 19 reviews

5 min walk to beach, private pool & spa, elevator

ThomasRating, 5 stars1 month ago
The house was absolutly perfect, even better then we expected. everything was perfect clean, there were suncreenes, shampoos, puzzles, beach toys, first aid and more. At our arrival we were greeted by snacks and a cake. during our stay we were able to see manatees every other day from the sundeck. the beach is only a five minute walk away and wonderful. Georgia was always reacting very fast for questions and was always helpful. we can absolutely recommend this house espacially also for children!
Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 54 reviews

Stunning New 3 bed 3 bath pool home by Siesta Key!

DeniseRating, 5 stars3 weeks ago
Really lovely home close to Siesta Key. Well maintained with a beautiful pool. Great place to stay! Adam was super responsive and answered my many questions, especially with us coming shortly after Helene hit and leaving early with Milton on the way.
Guest favorite

Home in Osprey

4.91 out of 5 average rating, 54 reviews

Private house with loft

MarciRating, 5 stars1 week ago
Amanda had a very cozy house and we thoroughly enjoyed our stay.
Guest favorite

Home in Holmes Beach

5 out of 5 average rating, 11 reviews

2 Unit Condo•BOTH INCLUDED•Heat Pool•Block 2 Beach

BrandonRating, 5 stars2 months ago
We had a large group at the house for our wedding on the beach, and the house was great! The few questions we had, Chris took care of immediately and made for a great experience! Everyone had a great time!
Guest favorite

Home in Sarasota

5 out of 5 average rating, 56 reviews

Cottage w/Fire Pit Near Siesta!

Atlante RentalsRating, 5 stars1 week ago
The place is beautiful, it looks like in the pictures, very big house and pretty, the bed sheets where smelling bad so we had to wash them again, but other than that everything else was great. Great location

Quick stats about house rentals in Longboat Key

  • Total rentals

    230 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    3.5K reviews

  • Family-friendly rentals

    200 properties are a good fit for families

  • Pet-friendly rentals

    100 properties allow pets

  • Rentals with a pool

    140 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Manatee County
  5. Longboat Key
  6. House rentals