Vacation rentals in Siesta Key

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Popular amenities for Siesta Key vacation rentals

Dog friendly vacation rentals in Siesta Key

Top guest favorite
A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.
Home in Sarasota
5 out of 5 average rating, 58 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

CharlieRating, 5 stars1 week ago
My wife and I had a great time at this stay. Lots to do at the house along with great beaches and restaurants within a 15-20 minute drive. The house was clean and had everything that you might need. We were able to drive to Disney in just over an hour and a half which provided a different experience to go along with the daily beach/pool trips. Cool AC inside to combat the humid 88 degree weather in June 2025.
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 stars2 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, 105 reviews

Spacious 2 Bedroom Home | Near Beach | Heated Pool

HeatherRating, 5 stars1 week ago
The stay was in a nice neighborhood. Enjoyed spending time at the pool there. The house was clean and free of clutter. When we had issues with the AC, Melissa responded right away and worked hard to fix the issue immediately. She refunded us the night as we stayed at a hotel with the house at 80. The AC got fixed the next day and we stayed our final night. Thanks Melissa for all your help making for a great stay.
Guest favorite
A screened-in pool area features a crystal-clear heated pool with lounge chairs positioned nearby. An umbrella provides shade over a seating area, surrounded by lush greenery and fencing that enhances privacy.
Home in Sarasota
4.95 out of 5 average rating, 211 reviews

2bed/2bath with POOL house, close by SIESTA KEY!!!

EmilyRating, 5 stars2 weeks ago
We absolutely loved our stay here! The house is beautiful and has everything we needed for vacation. The pool was perfect for the kids - they preferred staying home at the pool than going the beach. Romulda was also so helpful and responsive to all our questions. We only wished we had more time to stay here! We’re looking forward to booking again in the future!
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, 112 reviews

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

CarlosRating, 5 stars1 week 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.
Guest favorite
A cozy seating area features a brown futon against a wooden wall. A small table with purple metal chairs is situated nearby, next to a tall lamp with a warm glow. Decorative shelves display potted plants and artwork, creating a welcoming environment.
Guest suite in Sarasota
4.94 out of 5 average rating, 213 reviews

Sunshine Inn Paradise

JoshuaRating, 5 stars1 week ago
Visited from TN and had an awesome stay! Ron is a supremely chill host. Definitely recommend this BnB and would book again if I were in the area
Top guest favorite
A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.
Home in Siesta Key
4.91 out of 5 average rating, 120 reviews

Siesta Key, FL - Casa Berano

DarrylRating, 5 stars3 weeks ago
We thoroughly enjoyed our stay. The house was a private and calm place to come home to after our long beach days. We enjoyed spending our nights out by the pool. The pool lights we a nice touch. Would recommend to those who enjoy being in a quiet area.
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 stars4 weeks 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!

Family friendly vacation rentals in Siesta Key

Top guest favorite
A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.
Condo in Siesta Key
4.85 out of 5 average rating, 173 reviews

Best Siesta Key Condo

AndrewRating, 5 stars2 weeks ago
We had a very good time at Siesta Key and enjoyed our time at Maureen's place. The building is older, the amenities are well maintained and the condo itself is well cared for. I did find some mystery stains on the mattress and the decorative pillows in my room, but I'm guessing they are just spills that were difficult to get out. More importantly, the boat dock is usable, albeit with some difficulty if the boat is larger than 22 feet or so. We figured out on the second day that the best way to dock was parallel to the intracoastal between the posts and to tie off with lines on either side of the stern and with a single line on the bow. I would check ahead to make sure the dock is available, but we had no other boats docked there on a holiday weekend. The private beach access was a lifesaver on a holiday weekend, despite the short walk required to get there. Having both intracoastal and beach access is the biggest value of the place in my opinion.
Guest favorite
A wide view of a sandy beach features clusters of beachgoers enjoying the sun. Colorful beach chairs and umbrellas are scattered across the white sand. The gentle waves of the blue ocean can be seen in the distance, with high-rise buildings lining the shore.
Guest suite in Sarasota
4.94 out of 5 average rating, 248 reviews

2 Miles to Siesta Key

MilesRating, 5 stars2 weeks ago
Great location and walkable to close restaurants
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 stars3 weeks 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
The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.
Home in Sarasota
4.88 out of 5 average rating, 156 reviews

5 minutes to private Siesta Key Beach + 2 pools

DonnaRating, 5 stars1 month ago
Solen was an amazing host—very responsive, friendly, and helpful throughout our stay. She even brought us a brand-new can opener when we needed one! The house was spotless, cozy, and located in a great area. We had a wonderful time and would definitely stay again!
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, 516 reviews

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

JohnRating, 5 stars2 weeks ago
Elena and her husband were very gracious and kind, and we felt extremely welcomed from the start. We are moving to the area and Elena’s happy disposition and shining spirit was the perfect welcome to Sarasota, and she was naturally an emotional ambassador for us!!!! She made us feel at home!
Guest favorite
The enclosed Lanai features large bay windows showcasing views of the Gulf of Mexico. A seating area includes wicker chairs and a coffee table. Light-colored walls are contrasted by wooden accents and a ceiling fan, creating a bright and airy atmosphere.
Apartment in Siesta Key
4.93 out of 5 average rating, 108 reviews

Siesta Premier Location - The 'Calm of Siesta'

JasminRating, 5 stars2 weeks ago
I visit Sarasota every year and stay each time at a new place. This year I wanted to do something closer to the beach and Siesta Village. Matt’s spot was perfectly located for this due to being so close to the beach and every night we walked to the village for dinner/nightlife which was about 15 minutes walking distance. Overall a great place for 1-4 people if you’re looking for a nice chill vacation.
Top guest favorite
The exterior of the two-story condo building is visible, featuring a series of balconies adorned with umbrellas. Lush greenery surrounds circular seating areas with white chairs and tables, providing a relaxed outdoor atmosphere. Clear blue skies complement the setting.
Condo in Siesta Key
4.93 out of 5 average rating, 226 reviews

Private Siesta Key Escape

MelodyRating, 5 stars1 month ago
This little beach condo was perfect! In pristine condition, super cute, and very walkable to the beach and the trolley line. The downstairs laundry is currently out of service due to last fall’s hurricane, but that was ok with us. We would definitely stay here again!
Guest favorite
A private outdoor patio area is depicted, featuring a round table surrounded by four black chairs and a large umbrella providing shade. A charcoal grill is positioned to the side, and lush greenery and flowering plants enhance the tranquil setting.
Cottage in Sarasota
4.86 out of 5 average rating, 195 reviews

Drift Inn B Heated Pool & Private Beach Access!

KristiRating, 5 stars2 weeks ago
nice place to stay close to beach and right across from trolley pickup

Vacation rentals with pools in Siesta Key

Top guest favorite
Home in Sarasota
4.97 out of 5 average rating, 68 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

GabriellaRating, 5 stars5 days ago
This Airbnb exceeded every expectation! The property was beautiful, spotless, and incredibly well-maintained. The pool was a highlight—clean, peaceful, and the perfect spot to relax every day. The host was friendly, responsive, and made sure we had everything we needed for a comfortable stay.
Guest favorite
Home in Sarasota
4.97 out of 5 average rating, 68 reviews

Sun-filled cottage with pool, walk to beach

MichaelRating, 5 stars1 week ago
We loved our recent stay here! We had a bit of a challenge with lots of rainy weather so having a BEAUTIFUL backyard with synthetic grass and an amazing pool SAVED THE DAY(S). We ran outside with every break in the weather and the kids stayed as happy as can be. The home not only looked clean, but FELT clean and the decor was tasteful and didn’t feel overly beach kitschy- as we’ve run into before. Hoping to be back next year!
Guest favorite
A clear view of the ocean is presented, complemented by lush greenery in the foreground. Buildings line the coastline, and a blue sky with light clouds enhances the scene, creating an atmosphere of tranquility and connection to nature.
Condo in Siesta Key
4.95 out of 5 average rating, 19 reviews

Penthouse Expansive Ocean Views

AimeeRating, 5 stars1 month ago
Brenda’s place was just as listed. Great location, clean, great space to call home for the week. Within walking or short drive to many restaurants and shopping areas. Walk to the beach was easy especially with all the beach supplies in the condo. Brenda was also very responsive when I reached out with clarifying questions.
Top guest favorite
A modern, one-story villa is showcased with a light-colored exterior. The front door is flanked by tropical palm trees and vibrant landscaping. A paved driveway leads to an attached garage, enhancing accessibility in this coastal retreat.
Home in Sarasota
5 out of 5 average rating, 17 reviews

Ground floor home 2BD2BA garage Pool Private beach

NoraRating, 5 stars3 weeks ago
We had a fabulous stay! The location is perfect. The condo was spotless and nicely decorated. We had absolutely everything we needed. The private beach was clean and not crowded. Chairs were readily available. The location is great. There was an unexpected issue when we first arrived, but Amy was incredibly responsive and supportive, checking in regularly to make sure we were okay and comfortable. Her excellent communication and customer service was exceptional. Once everything was settled, we were able to fully enjoy the space and the beautiful surroundings. Can't wait to go back. We would definitely recommend booking this property.
Top guest favorite
Home in Siesta Key
4.99 out of 5 average rating, 78 reviews

Relax in a Private Tropical Retreat on Siesta Key!

SteveRating, 5 stars1 week ago
myself with my Partner Paula, daughter Sammy and her boyfriend Tom stayed at Jonathan's wonderful house for 2 weeks, starting May 25th 2025. We were all delighted with the house and fully equipped with all our needs. We made use of the communal pool and found those that lived in the community very helpful and friendly. We made use of the Breeze bus that was great for going to the village. I made contact with Jonathan a few times regarding minor things and he responded very quickly.
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, 148 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

AnnRating, 5 stars1 week 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!
Top guest favorite
A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.
Condo in Sarasota
5 out of 5 average rating, 45 reviews

Breathtaking Beachfront Views in Siesta Key

AverieRating, 5 stars1 week ago
this was by far our favorite vacation ever! the place was very clean, cozy, and perfect for our week. the hosts were very kind and responsive. can’t recommend this enough! siesta key was a beautiful place to stay, as well. so many good restaurants and little shops with lots to do! our favorite restaurant was spearfish 10/10 recommend. we will definitely be coming back again to this airbnb!
Superhost
A vibrant blue villa is positioned next to a clear swimming pool. Sun loungers are arranged on a sun deck, while palm trees provide a tropical background. The villa features multiple windows and a balcony, creating a light-filled atmosphere, complemented by the clear blue sky overhead.
Cottage in Siesta Key
4.86 out of 5 average rating, 259 reviews

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

HarryRating, 5 stars1 month ago
We really enjoyed our stay in the Treehouse Suite! The place was perfect & has described, very clean & cozy! Lisa was great, very friendly & accommodating. The location was also perfect, about a mile away from the busier part of town so it was quiet but the free modes of transportation made it really easy to get around. Definitely recommend!

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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  3. Florida
  4. Sarasota County
  5. Siesta Key