Holiday Homes in Longboat Key

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Find properties with these dates

Tonight
May 13 - May 14
Tomorrow
May 14 - May 15
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Featured Holiday Homes in Longboat Key

Sun-loungers, beach towels
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
10.0 out of 10, Exceptional, (6)
"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."
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Dining
Beach Cottage with a Private Hot Tub
10.0 out of 10, Exceptional, (54)
"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...
Beach Cottage with a Private Hot Tub
Property grounds
Short walk to beach or take your boat from the canal / dock in your backyard!
10.0 out of 10, Exceptional, (6)
"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."
Short walk to beach or take your boat from the canal / dock in your backyard!
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Fridge, microwave, oven, stovetop
Breathtaking Gulf Views Prestigious Long Boat Key
10.0 out of 10, Exceptional, (6)
"Second time here, would definitely return"
Breathtaking Gulf Views Prestigious Long Boat Key
On the beach
Waterfront home with private beach, a private pool, and water activities! Moku
10.0 out of 10, Exceptional, (1)
"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...
Waterfront home with private beach, a private pool, and water activities! Moku
Property grounds
Enjoy a Pontoon Boat and True Island Living at Pura Vida!
10.0 out of 10, Exceptional, (1)
"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...
Enjoy a Pontoon Boat and True Island Living at Pura Vida!
Aerial view
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
10.0 out of 10, Exceptional, (98)
"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."
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
Beach towels
Cedars East #526 Beautiful 2 bed 2 1/2 bath town home on Longboat Key. Sleeps 5
10.0 out of 10, Exceptional, (15)
"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...
Cedars East #526 Beautiful 2 bed 2 1/2 bath town home on Longboat Key. Sleeps 5
Aerial view
Island Living on Longboat Key 3 minute walk to the beach!
10.0 out of 10, Exceptional, (11)
"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"
Island Living on Longboat Key 3 minute walk to the beach!
Fridge, microwave, oven, stovetop
Cedars East #507 Townhouse by RVA
10.0 out of 10, Exceptional, (1)
Cedars East #507 Townhouse by RVA
Fridge, microwave, oven, stovetop
Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach
10.0 out of 10, Exceptional, (6)
"Fabulous back area!"
Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach
View from property
Piece of Paradise
10.0 out of 10, Exceptional, (3)
"Property was exactly as described. It was very clean and extremely well stocked. Neighborhood was quiet with quick beach access. Pam is a wonderful host and we would definitely book again!"
Piece of Paradise
Outdoor pool, a heated pool
Private townhome steps from the beach and right next to the pool
10.0 out of 10, Exceptional, (7)
"Great place great pool!! If you play tennis all clay courts very well maintained. The house was very well maintained and stocked with everything to get you started before getting your own provisions. Our only downside was the beach was along walk for us in our mid 70s. I rate this property 10 plus."
Private townhome steps from the beach and right next to the pool
Property grounds
Luxurious waterfront home with pool & spa…serene beach 5 min stroll away.
10.0 out of 10, Exceptional, (68)
"We have stayed in this house previously and hope to return! The house and location allows you to spend every day at the beach, by the pool, outside eating, listening and watching for birds and fish jumping, all while relaxing and enjoying time with family. We love the location and feel of house, outdoor space, and neighborhood. Beds are comfortable, kitchen is well appointed, easy access to bike rentals and beach, and very quiet. Hope to see you again next year!!! Thank you"
Luxurious waterfront home with pool & spa…serene beach 5 min stroll away.
Aerial view
Luxury Home with Private Beach Access and Heated Pool!
9.8 out of 10, Exceptional, (6)
"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."
Luxury Home with Private Beach Access and Heated Pool!
Exterior
Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
9.8 out of 10, Exceptional, (68)
"The house is full of charm; very clean and wonderfully equipped. Our kids had the best time fishing and playing in the water."
Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
Aerial view
Beautiful Beach Longboat Key Townhouse
9.8 out of 10, Exceptional, (10)
"Very nice/clean property…located near the center of Longboat Key. 5 minute walk to the beach and 10 minute walk to the bayside. Teenagers enjoyed playing soccer tennis and using the gym located in the community. Free Bike rental available. Would recommend visiting"
Beautiful Beach Longboat Key Townhouse
Aerial view
LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH!
9.6 out of 10, Exceptional, (64)
"We rented this house for a long summer vacation and it did not dissapoint! The house was comfortable and the property manager was quick to respond with repair requests whenever we needed help. The beach was gorgeous and the water was clean. The mosquitos were aweful, though, so make sure you take your insect repellent! LOL. I highly recommend this listing."
LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH!
Property grounds
2 BR Beach front villa with enclosed north bay
9.4 out of 10, Exceptional, (38)
"Comfortable cabin for 4 adults for a weekend trip to the beach. Equipped with everything we needed including beach umbrella, towels, cooler and beach chairs. Lovely screened in porch overlooking the pool. Great location. Highly recommend."
2 BR Beach front villa with enclosed north bay
Fridge, microwave, oven, stovetop
Cedars East #511 Townhome by RVA
9.4 out of 10, Exceptional, (3)
"It's a solid rental with lots of space, large w/d, garage for beach stuff and sunrise on the balcony. Just a 10' walk to the beach and a 5' walk to the pool. Sure could use updates to towels and bedding tho (threadbare throughout). Kitchen is stocked, although I'd recommend getting the knives out of the drawers! Good luck and hope the pool bar reopens."
Cedars East #511 Townhome by RVA
Don't see what you're looking for?
See all available properties in Longboat Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Longboat Key

On the beach, sun-loungers, beach towels
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
9.8 out of 10, Exceptional, (128)
"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."
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
Sun-loungers, beach towels
THE BEACH, condo #107, PRIVATE BEACH
9.8 out of 10, Exceptional, (54)
"Place was clean and excellent location but not quite as depicted from on line picture. Could not see water from patio chairs - had to stand on toes to see because large amounts of bushes obstructed view. Grill was right next to our room so people were walking in front of our room to use it and the entry way was in a dark hidden corner right next to community bathroom and community laundry. Would have been nicer to be on 2nd floor to see the ocean and have more privacy."
The price is NZ$698
includes taxes & fees
21 May - 22 May
THE BEACH, condo #107, PRIVATE BEACH
Property grounds
Direct Beachfront Gulf with Amazing Views
9.8 out of 10, Exceptional, (83)
"We absolutely loved this condo. It looks exactly as presented in the description. The location was great, and we loved spending our days at the beach! So convenient to restaurants and other attractions. Very relaxed, peaceful resort. We would definitely stay here again!!"
Direct Beachfront Gulf with Amazing Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Longboat Key Holiday Homes information

Number of reviews
392
Accommodation
108 Holiday Homes
Lowest Price
NZ$443
Highest Price
NZ$443

Recent Reviews in Longboat Key
Expedia verified reviews

Zota Beach Resort

Zota Beach Resort

5/5 Excellent
"Very nice staff and great environment. Highly recommend. Good mix of business travelers and families. "
A verified traveller stayed at Zota Beach Resort
Posted 1 day ago
Zota Beach Resort