
Vacation rentals in Siesta Key
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Top-rated vacation rentals in Siesta Key
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Popular amenities for Siesta Key vacation rentals
Dog friendly vacation rentals in Siesta Key

The Sand Castle - Backyard Oasis Mins from Siesta!
Loved our stay. Would stay again.

Spacious 2 Bedroom Home | Near Beach | Heated Pool
Melissa's listing was very nice and comfortable. The beds were comfortable and the ceiling fans worked great. The bathrooms were clean and the showers had good water pressure. There was lots to do in Venice and a drive to Sarasota was at most an hour. It was also nice that beach items were supplied, such as chairs, umbrella, coolers, etc. The house was also in a quiet neighborhood and we felt safe at all times. I would definitely recommend to others!

[escape to paradise] siesta key beach getaway
Wonderful stay! The location was great—just minutes from the beach and close to great restaurants. The house was as described: clean, comfortable and everything we needed. The host was very communicative and helpful. Highly recommend and would absolutely stay again!

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.

Tropical Retreat Close to Beaches |Pool |Game room
Absolutely loved our stay! The house looked exactly like the photos—beautiful, bright, and well-kept. Everything was spotless when we arrived. The host went above and beyond by providing tons of beach equipment, which made our beach days so easy and fun. The location was perfect—just a short walk to the marina, but tucked away in a quiet, peaceful area. Communication was seamless; the host was super responsive and helpful throughout. Would definitely stay here again and highly recommend it to anyone visiting the area!

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI
This was a great home for our family of six. We hope to return again.

Sweet & Simple guest suite Close to Everything.
Was perfect for me and my wife and we would recommend skyway jacks breakfast not too far down the street. Privacy was nice and had everything you could need in a single place. Would recommend.

The Cottage, very close to Siesta Beach!
Fair price. Great Location. Awesome / quick communication.
Family friendly vacation rentals in Siesta Key

Beach, Village, Dock & Private Pool! One-of-a-kind
Marko’s family home was beautiful, charming, and spotlessly clean. The home is perfectly located, walkable to beautiful beaches and great restaurants and shops, including the market. Marko was extremely hospitable, ensured we were all set and gave wonderful recommendations. We loved this place and will be back again next year. Thank you!

Cozy, Remodeled Studio Steps from Siesta Key Beach
Perfect spot right across from Sarasota Beach! Quiet, very clean, great pool, and very responsive host! We loved our stay and have favorited Vanessa as a host so we can check out her properties when we come back. Highly recommend this host and property for your trip to Siesta Key.

La Casetta: "the little house" near to the beaches
What a lovely place! The most well-equipped Airbnb I’ve stayed in; Elena has thought of every detail. Space is cozy and has everything you may possibly need. Beautiful tropical garden!

The Key Lime Cottage 2 miles from Siesta Key Beach
we stayed 5 days the space was clean with no traffic we where 5 min from the beach and seconds from food we have stayed at many Airbnb this one stood out with the provided beach towels umbrella beach chairs sunscreen everything needed to cook with the place had everything needed I dont even want to say it but the only thing missing was a. beach cooler but that's not the host responsibility thanks for a great stay hope to return next year

Pool & fenced-in yard in downtown edge bungalow
We loved it. Great place, great location and very cute, especially if you appreciate the quality and sturdiness of older homes. The pool is a huge bonus. Check in/checkout and everything in between is very easy and convenient.

Sarasota Downtown close to Lido Beach
Our stay at Inna & Vladimir's home was excellent. I had a work conference at a larger hotel about 4 min away. It was conveniently located, easy driving distance to restaurants and the beach, and in a safe part of town. We enjoyed the pool one evening and never felt bothered or out of place during our stay. The one thing to note is that, if you have any sort of chemical/fragrance sensitivity, be cautious the first day or two. My husband and I are both VERY sensitive and noticed the strong fragrant cleaner smells right away (tide, fabuloso type scents, etc). This likely wouldn't bother the typical person... but it was pretty intense for us. Considering those smells means that the Airbnb was cleaned, I can't complain about that! Lastly, if you have any mobility issues, the stairs are steep, but felt very sturdy. Overall, we would stay again. Thank you for your hospitality!

ROYS PLACE Romantic, Private, Paradise!
Roy’s place was comfortable, had good amenities, good location ( multiple beaches and restaurants in a close radius). The house was beautiful and just as described. The pool/hot tub, and outdoor seating was private and well maintained. Chairs, umbrella, and cooler were available to use which was a nice plus. We would definitely love to stay at this place again. Roy was quick to respond to any questions we had.

Sarasota guest house only 8 miles to Siesta Key
We LOVED our stay! It was easy to find and the neighborhood is very cozy and quiet. Perfect location to all the restaurants and a straight shot to the beach! Paulette was very helpful when it came to recommendations on food and activities! Her providing the umbrella, chairs, and cooler made the day at the beach amazing! The pictures do not do this place justice. Was so clean and decorated! 10/10 recommend. We will be returning!
Vacation rentals with pools in Siesta Key

The Velvet Blue house 3/2+Pool+5 min Siesta Key
Edina was extremely responsive (within minutes) when we had questions, also very accommodating when we wanted to extend our stay. The house is pristine, beautiful and spacious. The backyard with the pool very private and inviting! Definitely would come back the next time in Sarasota!

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Ivanna’s place was the perfect location for our family! Close to Siesta Key, yet in a private, quiet neighborhood. We loved the lush landscaping, and how well laid out the interior was. It was spotless! Our family also enjoyed the screened in porch and pool in the backyard in addition to that incredible cappuccino machine. I slept so well! Will definitely be staying again!

Pool, Spa, & Private Gym in the Heart of Sarasota
We had a great stay at the house. Loved the interior decor. Looks like the home was remodeled recently. Everything was fresh and clean. We loved hanging out by the pool. Backyard was very private and peaceful. Posts were very quick with their responses if I had any questions about the home. We would definitely stay at the Home again when we’re in town.

Sea Shell Ocean view On Beach Walk everywhere Pool
Loved the location and the layout of the condominium! We will be coming back!

"Enfuego!"
Such a perfect escape for a family or a group of friends! The backyard feels like you’re in a private tropical paradise. There are so many amenities in this home you barely need to leave! On days you want to hit the beach, it’s only about 10-15 minutes to get to Anna Maria Island - very convenient location. This was one of our favorite rentals which is well documented by all the photos we took throughout the home - swimming in the pristine pool with the waterfall and fire features glowing, playing golf, watching movies in the theatre, sun bathing on the real sand beach with tiki hut, beautiful loungers and so much more! We already have ideas about the different groups of friends we want to share this property with! Such a score and the hosts are delightful too!!

Cabana/Guest house w/spa/pool 5min to Siesta key.
We are very glad that we managed to choose this house. Large, spacious, with all the amenities and close to all the beautiful beaches. John is a big and kind person with an open heart and a bright soul. He does everything to make his guests feel comfortable. Thank you John.

Oceanfront Home with Heated Pool in Fishers Haven
House is immaculate! Super clean and comfortable. Beds and linens were luxurious! Ceiling fans in entry room including the screened in porch. Nice touch! Backyard waterfront is amazing. We used pool and hot tub multiple times per day. We fished off the dock and caught a few catfish. Sergiy was a perfect host. Excellent communication and direction when needed. Highly recommend!

Siesta Key Ground Floor Condo 2BR On Trolley Line
Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!
Quick stats about vacation rentals in Siesta Key
Total rentals
1.8K properties
Total number of reviews
32K reviews
Family-friendly rentals
1.5K properties are a good fit for families
Pet-friendly rentals
330 properties allow pets
Rentals with a pool
1.4K properties have a pool
Rentals with dedicated workspaces
820 properties have a dedicated workspace
Your guide to Siesta Key
All About Siesta Key
Siesta Key is an eight-mile-long barrier island off the coast of Sarasota, known for its soft quartz beaches, turquoise waters, and abundance of marine life. Due to its location on the western Florida shoreline in the balmy waters of the Gulf of Mexico, the island experiences ideal conditions year-round for swimming, paddling, and watersports. This small coastal community offers a host of recreational opportunities outside of the beach as well. Wander the Siesta Key Village, where you can find the many live music venues, boutique art shops, and souvenir vendors scattered throughout the small but lively downtown area. Check out one of the weekly farmer’s markets, spend an afternoon picking through the gift shops, or just lounge one the one of the white-sand beaches waiting for the sun to set over the Gulf.
The best time to stay in a vacation rental in Siesta Key
Thanks to the island's location in the Gulf of Mexico, weather conditions and water temperatures are favorable for most of the year. Beginning in March, temperatures start to rise, with averages peaking around mid October. You can expect heat and humidity at your Siesta Key rental during this period, but gulf stream breezes help keep things cool. Weekly farmers markets, a musical festival, and a fireworks show are just a few of the notable events happening through the summer season.
In winter, temperatures see a marginal decrease, with January and February being the coldest months. However, many still find both the air and water temperatures suitable for swimming. The winter also happens to be when many of the area’s art festivals take place. Check out the Chalk Art Festival towards the end of October or the sand sculpture competition in November where you can take sculpting classes and vote on your favorite piece of art.
Top things to do in Siesta Key
Point of Rocks
One of the best snorkeling sites on Siesta Key, this limestone rock outcropping is home to abundant marine life and migratory bird populations. Calm waters and clear conditions make this a perfect place for beginners and experienced snorkelers alike. Expect to see schools of tropical fish, crabs, ocean sponges, and manatees during the summer. You may even get lucky and spot some of the area’s resident dolphins.
Siesta Key Drum Circle
The Siesta Key drum circle is a weekly tradition held on Sundays at Englewood and Siesta beaches throughout the year. Beginning about an hour before sunset, local artists and dancers kick off an evening of music and dancing. Large crowds gather to watch the festivities as onlookers are encouraged to dance or grab a drum and beat along.
Deep-sea fishing
Sandwiched between the vast Gulf of Mexico and Roberts Bay, Siesta Key is a year-round fishing destination. The reefs attract cobia and grouper, and if you venture further out you’ll be rewarded with tuna and wahoo. July is peak season for red snapper, while the fall bait migration off the Florida coast is a big draw for anglers from October onward.
Frequently Asked Questions
How is the weather in Siesta Key?
Siesta Key enjoys a tropical climate with warm weather throughout the year. Summer temperatures can rise up to 90°F (32°C) while winter temperatures rarely drop below 50°F (10°C). The island gets a significant amount of rainfall, especially during the summer months.
What are some of the best things to do in Siesta Key?
Activities in Siesta Key often revolve around its beautiful beaches, where you can swim, sunbathe, or play beach volleyball. You can also explore the local shops and restaurants in Siesta Village, or take a boat tour to spot dolphins.
What is the best time of year to visit Siesta Key?
The most popular time to visit Siesta Key is during the winter and spring months when the weather is warm and comfortable. A notable local event is the Siesta Key Crystal Classic, an international sand sculpting festival that takes place every November.
What are the best places to stay in Siesta Key?
Popular areas to stay in Siesta Key include Siesta Village for its proximity to dining and shopping, Crescent Beach for its quiet atmosphere, and Turtle Beach for its family-friendly environment.
What are the best places to visit in Siesta Key?
Siesta Key is known for its stunning beaches such as Siesta Beach and Turtle Beach. You might also find exploring the Siesta Key Village and Point of Rocks interesting. The latter is a limestone formation on Crescent Beach attracting snorkeling enthusiasts.
What are some hiking trails in Siesta Key?
While Siesta Key is more known for its beautiful beaches, you can still explore walking trails such as the Palmer Point Beach trail or Turtle beach trail. These paths provide an opportunity to enjoy the island's natural beauty and spot local wildlife.
What are some family activities to do in Siesta Key?
Families can have fun exploring the Siesta Key beaches, perfect for swimming and building sandcastles. The Siesta Key Water Sports provide opportunities to engage in safe marine activities. For nature lovers, the Siesta Key Marina has dolphin watching tours.
What are some of the best day trip ideas in Siesta Key?
Popular day trips from Siesta Key include visiting the vibrant city of Sarasota, which has a lively arts scene, or exploring the Myakka River State Park, known for its diverse wildlife and hiking trails.
Are there vacation rentals with a dedicated workspace in Siesta Key?
Yes! Work meets play with ease at over 820 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in condo rentals in Siesta Key?
Experience the best of Siesta Key with our condo rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
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