
Condo holiday rentals in Longboat Key
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Top-rated condo rentals in Longboat Key
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Popular amenities for Longboat Key condo rentals
Weekly condo rentals

Beach Rd, 300ft to Beach Access & 500ft to Village
We always stay at Kyle’s property when we come to siesta key and love the location and the space everytime!! It literally has everything you need and is walkable distance to everything.

ON THE BEACH Condo, SPA -1 bd/1 ba. Location!
The place was exactly as advertised and I loved how close we were to the beach. It also was pretty private and the beach wasn’t crowded at all. Even though it was great, we probably wouldn’t stay here again because of the shower. My bf has had knee surgery and it was extremely difficult to get into the shower. The side of the tub was very very high, I had to lift my knee to my chest to get into the tub and my bf struggled a lot with his bad knee to do that to get into the shower. I still give the place 5 stars because it was as advertised I just didn’t realize from photos that the bathroom would be difficult for us to manage, and that’s our personal problem not a problem with the Airbnb. Everything else was perfect!

Beach Front Penthouse with Views
This is a beautiful, quiet and clean condo right on the beach. Great views and location to restaurants. The space had everything we needed stocked up.

Barefoot Mermaid 4, steps to the beach
We had a great stay here! Super close to the beach and shops / restaurants. Couldn’t have been a better location! The condo was comfortable and had everything we needed for our stay.

Sunset Villa D by Beach Boutique Rentals
We truly enjoyed our stay and the condo was perfect for what we needed. We enjoyed the ambiance by the outdoor pool and grill. The quick walk to the beach made it easy to view the amazing sunsets. The condo was very clean and the bed was so comfortable!

Salty Anchor by Coastal Chic Vacations
Love it! Everything about this place was perfect specially the location. The condo was sparkling clean. Not equipment with small/common kitchen goods like coffee or salt and pepper which I was very surprised but still loved it. Will definitely stay here again.

Prettiest Home on AMI! Gulf View - Still Renting!
Bryce was extremely responsive and his place was squeaky clean. Convenient location 1.5 blocks from the beach.

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO
Beautiful view of the Gulf of America to watch dolphins, shipping carriers and cruise ships coming and going. The beach area is mostly crushed shells until you get to the water. Nice seeing the beach was patrolled by police regularly even in a gated area. Was able to see Manatee in the canal and watch fishing boats coming and going. Parking was easy. Condo is very clean and well decorated with that comfortable relaxing feeling - we enjoyed the balcony for awesome sunsets and star gazing or our morning coffee. The restaurant/bars are not within walking distance but were only a short drive (all of them had good food). You pay by card for parking at most locations. We would definitely stay at this beautiful location again - one of my most relaxing trips.
Pet-friendly condo rentals

Heron's Hideaway- Studio by the bay!
Alison went above and beyond to make this trip everything and more. she was responsive, personable and kind. would stay here again and recommend to family/friends. five stars!

Waterside Studio in the heart of TI, walk to beach
My husband and I needed a little staycation after a stressful few months. The little apartment at the beach was perfect. The location was beautiful despite the fact that the area is still recovering from a few hurricanes last year. The host was also very helpful and gave some great recommendations. The only negative thing that I can say is that my stay was too short. I look forward to staying there again.

Beach Chill Inn #3 - Studio
This studio was a perfect and cozy little spot for my fiancée and I. Literal steps to the beach, ice cold AC, super clean, and very close to tons of shopping/eating/drinking spots. I would absolutely book this rental again for another weekend getaway!

Villa Al Golfo Pristine Waterfront Oasis
We honestly couldn’t have picked a better place to celebrate our birthdays. From the moment we arrived, the owners were so warm and inviting. They surprised us with a few welcome goodies, which was such a thoughtful touch and really made us feel at home right away. The unit was beautiful—clean, spacious, and honestly felt like a little slice of luxury. The bed was super comfortable, and the towels and bedding were incredibly soft and fresh—you can tell they really take pride in keeping everything in top shape. The view of the bay was amazing, and we got to watch dolphins swim by from the unit, which was just magical. They had canoes available for us to use, which made for a fun and peaceful afternoon out on the water. The location was perfect—just a short walk to the beach, shops, and restaurants. They gave us some great local restaurant recommendations too, and we ended up trying a few that we might have otherwise missed. Can’t wait to come back. Thanks Lyn & Frank

Anchor house +6 min. from Siesta Beach+heated pool
If you are looking for a place in Sarasota with everything you need closed to you like restaurants, dinner, food shopping etc at just minutes from siesta key then this is the place. Very clean and definitely what you see in pictures is what you getting. I stay here with m wife and two kids, we are very happy with pick this place, will definitely book again.

Amazing views on beachfront
It was a great stay with plenty of space and easy access to the beach. Just what we anticipated.

Charming and Updated 1 Bedroom in Runaway Bay
My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!

SHEEK and Glam- heated pool Updated! 3 mi to beach
sandra was amazing with communication and helping me check in and everything was beautiful she also had child floaters for my little one in the closet i really appreciated it i also noticed a tiny fork for him as well it was little things like that, that made me enjoy my stay even more. looked exactly like the pictures and smelled amazing i had so much fun and so did my family i will definitely be picking another one sandra's rentals😊
Condo rentals with a pool

"Jewel At The Shores" Gulf Front, sleeps 5
Excellent location! Everything you need is in the condo. Hope to come back soon!

Cozy Top-Floor Stay on Siesta Key + Bikes
Tonya is everything you want in a host- professional, prompt responses and excellent service. The apartment was clean and well appointed. We loved being so close to the beach and everything Siesta Key had to offer.

Condo On The Beach - Heated Pool - Self Check-in
This place is wonderful. First floor. Right out the door to the pool or beach. Community beach chairs for use and stunning views. It’s a very peaceful and quiet place compared to the public beaches. You can walk to a few different spots but it’s a little bit of a hike. The closest areas have some amazing views and food. We made food a few of the days. Having a kitchen and easy access to the beach is just unbeatable. We went to enjoy some fun in the sun and could not have been happier. Columbia, WaterColor, Kokomos, Grove Coffee, Latitude 28, and the shops next to Columbia were all excellent. The best food was probably Watercolor. We would 100% stay again.

Belleair Beach 215 Beachfront Gem Steps from Sand
This Airbnb has a GORGEOUS view! It was so peaceful to be able to sit on the balcony and watch the ocean. And the beach was right there to walk down to. Was well-worth it to spend a week here away from my busy job - I’m leaving relaxed.

2/2 JW Marriott Resort/Spa Clearwater Beach, 811
Absolutely perfect stay! This spacious, spotless 2/2 condo on the Clearwater Cut is ideally located near shops, restaurants, and nightlife. The private palm-shaded lounge and beach area felt like a hidden oasis, and it’s just a short walk to the stunning public beaches. The well-equipped layout made relaxing easy, and the balcony view was simply breathtaking. Can’t wait to come back and recharge again!

On the Beach; Siesta Key SunBum Studio
My daughter and I stayed for a mother daughter girls trip and had a blast! They made sure to take care of every little detail to make you feel comfortable and at home. Even checking in and making sure we made it ok. It was very clean and the location was amazing. Easy to get around on the trolly if we didn't want to drive and literally steps away from the beautiful white sand and clear turquoise beach. Do yourself a favor and book the trip!

Spectacular beach to bay views from this resort.
Our stay was great! The place and location were perfect! We had absolutely everything we needed. Communication was awesome! Thanks so much!! Lara and Thomas Boulder Co

King Oceanfront Suite! Kitchenette + Balcony!
Karen's place was an amazing clean spot with a great view. She was very friendly and helpful. I will definitely be back to stay here again. Can't beat tge location and all the fun stuff to do in the area
Quick stats about condo rentals in Longboat Key
Total rentals
450 properties
Nightly prices starting at
$83 NZD before taxes and fees
Total number of reviews
3.6K reviews
Family-friendly rentals
340 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
420 properties have a pool
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- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park