Search Vacation Homes in Longboat Key

"Two besties just getting away to relax and recharge our batteries. After a 12-hour drive, it was extremely comforting to enjoy your peaceful garden and an IMMACULATE beach cottage .... not one grain of sand anywhere inside. The amenities are perfect and plentiful. The water pressure is amazing and we appreciate the little things normally absent on vacation. We joked that it was time for a massage when it was shower time. Who has an outside shower with hot water ... this place! The daily wagon...

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"This was our family’s 1st stay and I can honestly say it won’t be our last!! Everything was perfect & we are so glad we found Hal’s hidden gem! Thank you for such a wonderful stay!"

"Room was clean, organized, and stocked with the essentials. Pool was extremely clean and well taken care of. Beach was beautiful and had plenty of complimentary chairs. Overall wonderful trip, will be booking again!"

"Perfect place for me and my family. I brought my boat down and fished almost every day. Even shared fish with the neighbors across the street. Great people on either side. Beds were comfy, grill worked great. Highly recommend."

"Last minute book that accommodated our family and fur baby. Home is very nicely decorated with plenty of beach accessories on a quiet street. Very little foot traffic surrounded by nature preserve. Beds were comfortable and plenty of pillows to spare. Pool was a nice reprieve from the beach and very private. Management company was top notch and had great communication throughout our stay. We would definitely book again."

"Second time here, would definitely return"

"We were searching for a unique vacation experience when we came across this listing on Vrbo, which definitely did not disappoint. It’s on an island with a very secluded beach surrounding it! You literally have to take a boat there, how cool is that and the wooden walkways all over really had a vibe! Our group really enjoyed our trip to the Anna Maria Island area, great food and shops, nice people, fanastic beaches. It was so nice to have our own private retreat and pool to relax in, we felt very...

"My husband and I enjoyed a two-week stay at this home in Longbeach Village. The home was as pictured with everything needed to make our stay hassle free. The neighborhood is lovely and quiet and close to the beach and a small shopping center with several great places to eat. It would have been helpful to have an information sheet with instructions on how to use the TV, days of trash pick up, and local suggestions. Otherwise, we had a wonderful time and would come back again."

"Our family trip to this area was made absolutely unforgettable by staying here. This vacation rental home on a private island near Anna Maria Island was simply incredible. Accessible only by boat, the seclusion and tranquility were unbeatable. The private beach was just steps away from our doorstep, and was a paradise for our kiddos to play at building sandcastles and for us to relax. The roomy house and bedrooms were perfect for our crew of six, making every day together easy to enjoy. With a...

"The home is well maintained and updated. The location is beyond amazing. The owner was responsive to our email questions and the property manager was excellent. We had a fabulous family vacation."

"The house is full of charm; very clean and wonderfully equipped. Our kids had the best time fishing and playing in the water."

"We really enjoyed our stay. Check In/Out process was easy and communication was great. The unit was very clean with a well stocked kitchen. There are a lot of beach toys, chairs, etc for a great day at the beach. Probably the most we have ever seen at a beach area condo. Also, having a garage for the car was really nice. The complex itself was great and the pool was amazing. It is 4ft deep all around with plenty of room for the kids to have fun while not bothering others. We even played some...

"We had never been to this area of Florida before...so we were not sure if we were missing out by not staying in Anna Maria Island. We got so lucky! Longboat Key was the perfect spot for a relaxing vacation with an 1 1/2 year old. We loved have the option to walk across the street to a beautiful private beach, or to utilize the"

"We loved the condo. It's very roomy and modern. The pool is big and convenient, but it could use more lounges and umbrellas. There are many tennis courts and some pickle ball courts for those that like to play. The beach is across the street, less than 10 minute walk. Our first time in Longboat, and we like the island. More laid back than Siesta Key, and has some great restaurants. we loved the Mariachi band at the nearby Mexican restaurant. Folks should try to get to the Mote Aquarium, it is a...

"Simple place. Easy access. Baden ones but all one needs"

"Property was nice and quiet. Concerns were addressed quickly"

"The beach is beatiful on this Key. The Sea Beach is old but it was good for the price and right on the beach. We just needed a place to sleep so it was fine. No beach towels provided but they do have lounge chairs. On this key u have to Uber everywhere. Nothing is in walking distance."

"This two bedroom condo was perfect for our family needs. My two kids (preteen girl and teen boy) had their own space and my husband and I appreciated the king bed (my husband is tall, so a king is better than a queen). Everything we needed for the weekend was in the condo. The proximity to the beach, dinner options and even fishing on the pier were exactly what we were looking for. We have been to many gulf beaches and we liked how quite this was vs bigger public beaches."

"Sand Cay is amazing!"