
Condo vacation rentals in Siesta Key
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Top-rated condo rentals in Siesta Key
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Popular amenities for Siesta Key condo rentals
Condo rentals with a pool

Stunning Siesta Vistas Direct Beach Access & Pool
I rented this place for my parents. They like it so much. The host is very responsible. I highly recommend this place

Beach Haven on Siesta Key Beach
We loved our stay at this condo. Such a great location and close walk to the beach and playground. The condo is clean, airy, comfortable and had everything we needed for our stay. We loved the two balconies. The owner let us burrow a cart to haul the chairs that was also provided for the beach. My son especially loved playing with the boogie boards, also provided. Would definitely stay here again.

Amazing beach view! Entire unit renovated!
Such a beautiful place to stay! Very clean! The kitchen was stocked with all the dishes you will need. The view was amazing!!! The free trolly into the village was so easy. The beach accessories were so nice to use. All we had to do was cross the street and we were on the beach. The pool area was also very nice! Grilling area was nice and clean and a small smoking area so my husband could enjoy a few cigars. Great communication! Thank you! Was a fantastic vacation!

Breathtaking Beachfront Views in Siesta Key
Very nice unit, nice and clean, they had everything someone will need to have nice beach trip, Raquel was amazing in her assistance throughout the stay

Siesta Key condo - Gulf and bay club bayside
We had a great stay in Siesta Key. The grounds were beautifully kept. Pool right out the back door. Quick walk to one of the most beautiful beaches in the US. Great week, can’t wait to go back.

Charming Bayfront 2 BRs Siesta Key Condo
The condo was very comfortable and clean! I stayed an extra day and Tee was very accommodating and easy to get in touch with. People in the condo community where very friendly. I especially liked that I had a specific covered parking spot each time I returned, so there were no problems with parking. I frequent Siesta Key and this location on the bay side is nice!

Cottage on Siesta Key Your own getaway!
Julie was a fantastic host. Responded to all questions in a very timely manner. She went above and beyond to make sure my girls group had a good time! Trolley service is at the curb to take you to the village or elsewhere. Restaurants are right across the street for breakfast, lunch, and dinner, so no cooking was needed for us! Thank you for a great experience.

Beachfront - 2BR - Spectacular Beach Setting
Loved our stay here! The condo has everything you think you’ll need- coffee filters, laundry detergent, beach toys/chairs, boogie boards, shampoo/conditioner, beach towels, etc. The home was clean and exactly as the pictures show. The proximity to the beach was what sold us on this location, and there’s restaurants and stores within walking distance. We had a rental car, but there’s also a trolley that takes you from this area to the downtown area a few min away. All of the hosts instructions were very clear and the condo was easy to access. We expected to hear some noise here and there, but it was very quiet and peaceful. We felt so comfortable and happy here! We will absolutely come back!
Family-friendly condo rentals

Steps from the beach
Monika’s place is a well kept, updated condo, with access to a lovely pool. Easy to find, a quick walk to Publix grocery and restaurants. The small balcony off the main bedroom is perfect for morning reading. 270 steps to the beach, 450 steps to the water. We used 38th Street to cross the busier road to get to a less crowded area of the beach. The beach was beautiful, didn’t see evidence of hurricanes. Beach in February was not crowded. There are three other condos in the building. The neighbors were quiet and kind.

Steps away from beach and village! #1 in Siesta!
We had a great time in Siesta Key and this place was exactly what our family needed. It was a quick walk to the beach, even with a stroller and wagon! We brought a stroller but didn’t even need to because the same one was waiting in the closet! The beach was beautiful and not too crowded. The place was well stocked with things we needed to eat in but very close to many restaurants for the nights we went to dinner. VK was very responsive to the couple questions we had and informative on area attractions.

Sun, Beach Views, and Smiles!!!
Fabulous space with an outstanding location. Walked to get all groceries and eat at wonderful restaurants. Pool area was nice with afternoon sun and just steps to the beach. Thanks Margie!

Best Deals on Siesta Key
Fantastic location! Easy to walk to restaurants and there is also a free trolley if you do not have a car. The room was very clean, well equipped, and perfect for our five day stay in Siesta Key. The designated parking spot was a plus because parking is at a premium. I only needed to talk to Bernadette once and she was very quick to respond. We will definitely be coming back! My only complaint is we couldn’t stay longer.

5209B Menorca Street - Siesta Key Village Condo
Easy check in. Very close to everything. Pool was a great extra !

Anna Maria Island-just a few steps to the beach
Great place to stay and so close to beach. We had such a great time will definitely book again.

Tropical Paradise Destination
We stayed 4 nights at Robin's place and had a wonderful time. The unit felt homey with beach chairs, towels, a frisbee, football, umbrella, etc. The unit was clean, well-maintained and had everything we could have asked for. We had a relaxing trip and loved the easy walk *right* across the street to a beautiful beach. We actually got engaged at Bean Point on night 1 of our trip- the next several days felt like a mini honeymoon! Will definitely be back to the island and hope to find availability at Robin's place when that time comes. Thank you, Robin, for the clean, accessible, and well-equipped stay!

Location,Location,Location-Beachfront-Siesta Key
We had an AMAZING stay! We originally booked the week of the hurricane in Nov. He was so great at letting us know the impact, and refunded our money, no questions asked. We rebooked for May, and couldn’t have had a better time! Great condo! So many things in walking distance. We are very grateful for all his kindness and communication! You can tell he takes pride and loves this condo.
Weekly condo rentals

Enchanting Coastal Ambiance & Breathtaking Sunsets
home was very clean and cozy!! everything was in walking distance and close to the beach, restaurants and shops were walkable distance 😊

Amazing SK beach views... Newly renovated condo!!!
We really enjoyed our stay! The unit was clean and pretty true to the pictures. Jamie was always quick to respond to any question we had. The location to the beach was awesome, and we appreciated having the beach chairs and other beach items that were supplied! We also enjoyed using the facilities pool, where there were quite a few friendly people there. In addition, we enjoyed the 2 balconies, and liked that there were different sitting areas and views to enjoy. The trolley stop right outside the building was a nice feature to have as well! Overall, it was a nice place to stay with clear directions, an easy check in/out process, and all of the things we needed.

Siesta Key Oceanfront View Condo - unit 407
Absolutely beautiful location. The unit is in the center of the building on the 4th floor, which gives you the best view of the beach and gulf. Frog hop shuttle was extremely good, very quick pick up times and it’s free besides the tip for your driver. All in all, amazing location, beautiful and spotless unit. Such great vibes here, highly recommend.

Siesta Oceanview Retreat-1 min walking to beach
Really nice home, was very clean when we arrived and had everything we could have needed at a home away from home. Fantastic location, short walk across the street and you’re at the beach. Would definitely recommend and stay here again. Host was great as well and very responsive with clear instructions.

Vacation Delight at Chasing Sunshine at Lido Key.
My mom and I got away for a long Mothers Day / birthday weekend at Sue's place. Exactly as pictured and advertised. We enjoyed the beach by day and St. Armonds Circle each night. walked home each night feeling safe! The bed and pillows were extra compfy! I would definitely return here and hope to again soon! Thanks Sue for the wonderful stay and quick communication when I missed some details needed. 🙃

Casa Mar Steps 2 Siesta Key, Pool, Tennis, & More!
After two years of visiting this has become my one week oasis once a year! The pool is basically your backyard. The room itself is small but very homey, cozy and perfect for 2 people. Easy to cook dinner or just pop in and out for easy lunches. IT IS SO NICE being steps from the pool and just a minutes in sand to get to the ocean waters. Beach chairs are free to use. Towels are provided. The most precious clothes lines hangs out back for easy and free drying! The community is sooo kind. Do yourself a favor and say hi! You’ll be amazed by the lifelong friendships you can make! Restaurants are close by and the community is always willing to help you with recommendations! Hosts are quick to respond, we had a microwave issue and it was resolved within 12 hours! Very easy to communicate with! Overall I love our little community for the one week I get :) it will now always be a yearly vacation for me. I’ve met some lifelong friends!

BEACH FRONT PARADISE
This was our second year staying here. The view is amazing!! It is very clean and well stocked.

Sarasota Surf & Racquet Club Siesta Key Condo
We truly enjoyed our time in Siesta Key. Our only regret was that we couldn’t stay longer! The location was great. The beach was beautiful. Accommodations were clean and comfortable. Jennifer was very quick to reply with any information requested, and she gave us some great local recommendations. Check in and check out were very easy. It was a great experience!
Quick stats about condo rentals in Siesta Key
Total rentals
980 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
15K reviews
Family-friendly rentals
790 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
810 properties have a pool
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- John's Pass
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Raymond James Stadium
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Streamsong Resort
- Jannus Live
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park