Longboat Key Vacation Rentals

January 2025

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February 2025

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Vacation Rentals in Longboat Key

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (301)
"I love that this property is right on the beach. We were there over Christmas. The property was not fully booked, so it was fairly quiet. The Gulf was too cold for us, but we enjoyed using the the provided lounge chairs to relax on the beach. Lots of shelling to do. Not a lot of people at this time. Pool was not a bad temperature and was clean. The property looks like an old motor lodge, but they have kept it nice. Our room did not have a lot of updates, but it was sufficient. A roll of paper...
Sea Club I Beach Resort

Silver Sands #236 Resort by RVA

9.2 out of 10, Wonderful, (62)
"Fantastic!"
Silver Sands #236 Resort by RVA

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

9.8 out of 10, Exceptional, (137)
"Cute little cottage with 2br, 1ba. Very clean, close to the beach. Lots of supplies for the beach. Could use softer towels in bathroom and perhaps some instructions on the shower as it was quite hot on any setting. Prior communication was slow but once there was pretty attentive. "
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

Luxury Beach Condo with Breathtaking PROMO AUGUST- 2024 -175- NIGHT BEST PRICE!

9.8 out of 10, Exceptional, (230)
"You can't find a better spot right on the beach in Longboat Key or just about anywhere else on this part of the Gulf Coast. While the recent hurricanes did take their toll on the greenery surrounding this place, the unit itself was untouched and just as great as ever. Our second time to stay here and that should say it all."
Luxury Beach Condo with Breathtaking PROMO AUGUST- 2024 -175- NIGHT BEST PRICE!

Longboat Key beach house - 5 min walk to the beaches and top local restaurants

9.6 out of 10, Exceptional, (13)
"The property looked exactly like the photos. It was clean, in a very quiet neighbourhood close to the beach & some good restaurants. Beds were comfortable. Kitchen could have done with more stock (there were 8 of us staying & not enough crockery or cutlery) but wasn’t a huge issue. We loved the location & how quiet it was, so would definitely stay again."
Longboat Key beach house - 5 min walk to the beaches and top local restaurants

Beautiful Beach Longboat Key Townhouse

10.0 out of 10, Exceptional, (15)
"Such a wonderful place! We had one of the best family stays ever. Viktor’s place was absolutely perfect for us (a family with two teenagers). We felt as we were at home. Not only was it extraordinarily equipped, but it was also comfortable, spacious, bright, and in an incredibly beautiful area. The beach is dreamy and 5 min walk. If we could, we would give you 6 stars! Thank you so much for making our stay unforgettable! Love from Argentina!"
Beautiful Beach Longboat Key Townhouse

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (131)
"Overall good property. Needs a gym and hot tub and a volleyball net out on the sand would be fun. Very friendly staff, good pool, great beach. "
Breathtaking Beach Front Property Ground Floor Condo

Beach view. Year-round Balcony Sunsets. Just renovated.

9.8 out of 10, Exceptional, (76)
"Beautiful view.. home was clean and the front staff was amazing. "
The price is ¥29,249
¥66,648 total
includes taxes & fees
Jan 18 - Jan 19
Beach view. Year-round Balcony Sunsets. Just renovated.

Beach View Condo- Quiet & Secluded with Private Beach

10.0 out of 10, Exceptional, (22)
"10/10! We stayed at this property Nov 21-26 (my mom, 2 boys age 5 and 7, and myself). The property was easy to get to (25 min drive from Sarasota-Bradenton), check-in was effortless (host sent a code), and the property was very clean and quiet. When you see how close the beach is in the pictures, that truly is how close it is! The chairs on the beach were super convenient. The seller was an excellent communicator! She kept in touch with us after the hurricane and was upfront about issues caused...
Beach View Condo- Quiet & Secluded with Private Beach

Panoramic beach View and amazing Sunset.

9.8 out of 10, Exceptional, (95)
"Beautiful unit!"
The price is ¥54,545
¥99,343 total
includes taxes & fees
Feb 1 - Feb 2
Panoramic beach View and amazing Sunset.

Open Tonight, $100/nt!

10.0 out of 10, Exceptional, (65)
"Our stay was amazing! A perfect beach condo for a family with young kids, short walk to the beautiful beach & pool! Heidi was a wonderful host, very thorough & so kind! This was our first visit to Longboat Key, we loved it! Would highly recommend this condo & hope to return in the future! "
The price is ¥27,668
¥60,497 total
includes taxes & fees
Jan 14 - Jan 15
Open Tonight, $100/nt!

THE BEACH, condo #107, PRIVATE BEACH Open 1/1/2025

9.8 out of 10, Exceptional, (60)
"Very nice "
The price is ¥44,953
¥78,289 total
includes taxes & fees
Feb 8 - Feb 9
THE BEACH, condo #107, PRIVATE BEACH Open 1/1/2025

Direct Beachfront Gulf with Amazing Views

9.8 out of 10, Exceptional, (90)
"What a fantastic spot. The beach was terrific… the condo had every amenity we needed…. The pool was lovely. Dolphins and manatees in the water… close to restaurants and shopping. Beautiful sunsets and storm watching. We are so sad to be leaving because we had such an amazing vacation. I can’t think of a single thing we would have done differently. Thank you!!!"
Direct Beachfront Gulf with Amazing Views

Updated Beachfront Condo at Prestigious Long Boat Key Resort

8.6 out of 10, Excellent, (11)
"Secluded property in a gated community. Beach and ocean views tremendous. Loved sitting on the balcony (which is twice as long as the picture) and drinking coffee while relaxing in the morning."
The price is ¥81,231
¥160,907 total
includes taxes & fees
Jan 19 - Jan 20
Updated Beachfront Condo at Prestigious Long Boat Key Resort

The Beach on Longboat Key #220 Resort by RVA

8.0 out of 10, Very Good, (42)
"We enjoyed our stay! We had all the necessaries for a few days at the beach. It’s a great price point if you’re just looking for a little rest on the beach. There are local restaurants just a few miles down the road. The only think I would suggest is that the property provide a broom for the room. You’re at the beach so of course, there is going to be sand. We are planning on coming back. "
The Beach on Longboat Key #220 Resort by RVA

Waterfront home with private beach, a private pool, and water activities! Moku

10.0 out of 10, Exceptional, (2)
"We had a great stay! It was definitely an experience. It was a peaceful island getaway. If you are able to stay here I recommend it! Any issues we had the AMI team had a quick and efficient response-the only issues we had was our door code didn’t work for all the doors but they responded quickly and got us in in a blink of an eye, and the trash bins outside were almost full but they were out the next day to empty them so no complaints with that! Our only thing was the water in the house is VERY...
Waterfront home with private beach, a private pool, and water activities! Moku

Beachfront With Incredible Panoramic Gulf View and The Most Beautiful Sunset.

9.8 out of 10, Exceptional, (129)
"This condo was very impressive. Everything was clean and well maintained. The staff was very engaging. But the sunsets were spectacular. We were right on the ocean!"
Beachfront With Incredible Panoramic Gulf View and The Most Beautiful Sunset.

Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.

9.8 out of 10, Exceptional, (54)
"Great location! You won’t be disappointed. The beach is just steps away. Communication with the owner was the best! We needed more blankets(my kids don’t share). Owner answered on the first call and had it handled in minutes. Condo was super clean, adorable and had everything we needed. Thank you for allowing us to stay."
Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.

Silver Sands #237 Resort by RVA

9.0 out of 10, Wonderful, (38)
"Steps to the beach and included towels, beach chairs and umbrellas. Staff was extremely nice and we enjoyed the joke of the day while checking in!"
Silver Sands #237 Resort by RVA

Turtle Shores BEACHFRONT Retreat! Waterfront oasis to completely unwind!

9.8 out of 10, Exceptional, (16)
"What a charming condo that is a short, well kept walk to the gulf! Our stay was so peaceful and the beach was not crowded at all. The condo was well maintained, clean and had all that we needed for our stay, even beach towels, beach chairs and an umbrella! We didn’t use the pool yet it looked clean and cared for. There was a building on the property which you see immediately when you pull in which is very run down and falling apart. It’s a shame to see yet did not affect our experience at...
Turtle Shores BEACHFRONT Retreat! Waterfront oasis to completely unwind!
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.
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Other types of properties in Longboat Key you may be interested in

Zota Beach Resort

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Zota resort exceeded our expectations with excellent service, spacious room, luxurious bedding and toiletries, direct access to a great beach."
The price is ¥47,161
¥60,358 total
includes taxes & fees
Jan 12 - Jan 13
Zota Beach Resort

The St. Regis Longboat Key Resort

5.0 star property
10.0 out of 10, Exceptional, (10)
"Loved it"
The price is ¥156,153
¥186,256 total
includes taxes & fees
Jan 12 - Jan 13
The St. Regis Longboat Key Resort

The Resort at Longboat Key Club

4.0 star property
9.0 out of 10, Wonderful, (639)
"Staff excellent. Elevators need work. Rooms very nice. Beach excellent "
The price is ¥84,228
¥102,307 total
includes taxes & fees
Jan 12 - Jan 13
The Resort at Longboat Key Club
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.

Frequently asked questions

Can I find a vacation rental in Longboat Key?

Yes, we have vacation rentals near popular local attractions in Longboat Key, or you can go with a secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the popular beaches in Longboat Key. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals that Longboat Key has to offer?

SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B: This vacation home near Longboat Key is on the beach and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Longboat Key?

Choose from 179 Expedia vacation rentals in Longboat Key for a memorable vacation.

What can I see and do in Longboat Key?

Longboat Key Beaches and Jewfish Key are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Cannons Marina and Harborside Golf Course at Longboat Key Club.

What are vacation rentals like in Longboat Key?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Longboat Key. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.