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Vacation rentals in Siesta Key

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Popular amenities for Siesta Key vacation rentals

Dog friendly vacation rentals in Siesta Key

Guest favorite
A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.
Home in Sarasota
4.95 out of 5 average rating, 131 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

PhilRating, 5 stars3 weeks ago
Loved our stay. Would stay again.
Guest favorite
An outdoor lanai features a swimming pool surrounded by a screened enclosure, providing a secure and open space. Comfortable seating arrangements are visible, with a decorative rug underfoot. Lush greenery can be seen beyond the pool area, enhancing the tranquil setting.
Home in Venice
4.95 out of 5 average rating, 107 reviews

Spacious 2 Bedroom Home | Near Beach | Heated Pool

SarahRating, 5 stars1 day ago
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!
Superhost
A spacious patio area features two lounge chairs and a large umbrella, surrounded by tropical plants. A stone pathway leads through the gravel garden, enhancing the outdoor atmosphere. Decorative planters add color against the lush greenery, creating a serene retreat.
Home in Siesta Key
4.88 out of 5 average rating, 104 reviews

[escape to paradise] siesta key beach getaway

PhilRating, 5 stars1 week ago
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!
Guest favorite
A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.
Condo in Sarasota
4.87 out of 5 average rating, 113 reviews

Anchor house +6 min. from Siesta Beach+heated pool

CarlosRating, 5 stars2 weeks ago
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.
Top guest favorite
A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.
Villa in Sarasota
5 out of 5 average rating, 103 reviews

Tropical Retreat Close to Beaches |Pool |Game room

Alistair LanceRating, 5 stars1 month ago
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!
Guest favorite
A serene outdoor space features a sparkling pool surrounded by lush greenery and tropical plants. Comfortable lounge chairs are placed along the poolside, and string lights cast a warm glow overhead. A shaded seating area with a gazebo can be seen in the background.
Home in Bradenton
4.92 out of 5 average rating, 369 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

BettyRating, 5 stars3 days ago
This was a great home for our family of six. We hope to return again.
Guest favorite
A welcoming exterior showcases a bright yellow door framed by grey walls and distinctive column accents. Lush green grass surrounds the entrance, complemented by flowering shrubs near the pathway. Two large windows allow natural light to illuminate the space, creating an inviting first impression.
Guest suite in St. Petersburg
4.91 out of 5 average rating, 254 reviews

Sweet & Simple guest suite Close to Everything.

KeoniRating, 5 stars2 days ago
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.
Top guest favorite
A spacious room features a king size bed with coordinating pillows and light bedding. A chic chandelier hangs from the ceiling, illuminating the space. Natural light enters through the window, while a comfortable seating area with decorative pillows and a coffee table complete the inviting environment.
Guesthouse in Sarasota
4.87 out of 5 average rating, 415 reviews

The Cottage, very close to Siesta Beach!

PaulRating, 5 stars3 weeks ago
Fair price. Great Location. Awesome / quick communication.

Family friendly vacation rentals in Siesta Key

Top guest favorite
A charming cottage is depicted with light blue wooden siding and white accents. The front yard is gravelled, surrounded by landscaping featuring mature trees and shrubs. A welcoming porch with a railing leads to the main entrance, enhancing the property's inviting look.
Home in Siesta Key
5 out of 5 average rating, 144 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

ZacharyRating, 5 stars1 month ago
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!
Guest favorite
An open-concept living area features a bright red sofa adorned with colorful cushions. A glass coffee table sits in front of the sofa, and a round dining table with wooden chairs is positioned nearby. The kitchen is visible in the background, with modern appliances and light cabinetry.
Apartment in Siesta Key
4.81 out of 5 average rating, 242 reviews

Cozy, Remodeled Studio Steps from Siesta Key Beach

MattRating, 5 stars2 weeks ago
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.
Guest favorite
A tranquil beach scene is depicted, showcasing crystal-clear waters that blend from turquoise to green. A person stands waist-deep in the water, with a horizon extending into the distance. Driftwood and natural debris adorn the sandy shore under a bright blue sky with scattered clouds.
Guesthouse in Sarasota
4.92 out of 5 average rating, 517 reviews

La Casetta: "the little house" near to the beaches

RachelRating, 5 stars1 week ago
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!
Guest favorite
A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.
Home in Sarasota
4.95 out of 5 average rating, 242 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

ScottRating, 5 stars3 weeks ago
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
Guest favorite
A screened-in patio features a round table with decorative tile and four chairs, surrounded by lush greenery. A pool is visible in the background, reflecting the clear blue sky, providing a serene setting for relaxation and outdoor dining.
Bungalow in Sarasota
4.91 out of 5 average rating, 350 reviews

Pool & fenced-in yard in downtown edge bungalow

AmiRating, 5 stars2 weeks ago
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.
Guest favorite
A bright pool area is enclosed by a screened structure, featuring a sparkling pool with a curved edge. A detached two-story apartment stands adjacent, accessible by stairs. Lush greenery and potted plants enhance the serene atmosphere, creating a residential retreat.
Apartment in Downtown Sarasota
4.85 out of 5 average rating, 325 reviews

Sarasota Downtown close to Lido Beach

AmyRating, 5 stars2 weeks ago
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!
Top guest favorite
The enclosed pool area is surrounded by lush greenery and tropical plants, with vibrant purple lighting creating a serene ambiance. A spacious swimming pool reflects the colors overhead, while a decorative wall clock adds a charming touch. Comfortable seating is present along the edges.
Apartment in Indian Beach-Sapphire Shores
4.96 out of 5 average rating, 169 reviews

ROYS PLACE Romantic, Private, Paradise!

KellyRating, 5 stars3 weeks ago
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.
Top guest favorite
A spacious bedroom features a king-size bed adorned with a blue and white textured coverlet. Soft natural light filters through the window, illuminating the room, which includes a nightstand, dresser, and a comfortable bench at the foot of the bed.
Guesthouse in Sarasota
4.97 out of 5 average rating, 276 reviews

Sarasota guest house only 8 miles to Siesta Key

LoraRating, 5 stars2 weeks ago
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

Superhost
A screened-in patio encloses a private pool, featuring a pink inflatable flamingo in the water. Lounge chairs are positioned around the pool area, and a hanging chair is visible in the corner. Lush greenery surrounds the space, offering a sense of privacy.
Home in Sarasota
4.83 out of 5 average rating, 6 reviews

The Velvet Blue house 3/2+Pool+5 min Siesta Key

JeffRating, 5 stars2 weeks ago
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!
Top guest favorite
Home in Sarasota
4.97 out of 5 average rating, 69 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

SuAnnRating, 5 stars1 day ago
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!
Guest favorite
A clear swimming pool reflects the evening sky, surrounded by a spacious patio. Outdoor seating for dining is arranged under an umbrella, with chairs positioned nearby. Lush greenery provides privacy, and large glass doors lead to the inviting interior of the home.
Home in Sarasota
5 out of 5 average rating, 6 reviews

Pool, Spa, & Private Gym in the Heart of Sarasota

NatalyaRating, 5 stars1 week ago
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.
Guest favorite
A spacious pool area is shown, framed with palm trees and lounge chairs under bright blue umbrellas. The inviting water reflects the sky, while a building with large windows is visible in the background, offering a comfortable area for relaxation.
Condo in Siesta Key
4.91 out of 5 average rating, 127 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

MariaRating, 5 stars1 week ago
Loved the location and the layout of the condominium! We will be coming back!
Superhost
Home in Bradenton
4.86 out of 5 average rating, 7 reviews

"Enfuego!"

AmandaRating, 5 starstoday
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!!
Guest favorite
A serene pool area is enclosed by a screened structure, featuring a small circular spa at its center. Soft lighting enhances the space, and several benches are positioned around the pool. Potted plants add greenery, while the surrounding walls are painted in a subtle hue.
Guesthouse in Sarasota
4.93 out of 5 average rating, 88 reviews

Cabana/Guest house w/spa/pool 5min to Siesta key.

СергейRating, 5 stars1 month ago
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.
Guest favorite
A relaxing outdoor space features a sparkling swimming pool surrounded by lounge chairs with red and white stripes. Tall palm trees stand nearby, adding a tropical touch, while serene water views and lush greenery are visible in the background.
Home in Sarasota
4.91 out of 5 average rating, 58 reviews

Oceanfront Home with Heated Pool in Fishers Haven

DinaRating, 5 stars2 months ago
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!
Guest favorite
A large heated pool is visible, surrounded by lounge chairs for relaxation. Tall palm trees frame the area, and the building's exterior provides a backdrop. The clear blue water reflects the sunny sky, inviting guests to enjoy a refreshing swim.
Condo in Sarasota
4.86 out of 5 average rating, 149 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

AnnRating, 5 stars2 weeks ago
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.

Destinations to explore

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