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Condo vacation rentals in Siesta Key

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Popular amenities for Siesta Key condo rentals

Condo rentals with a pool

Guest favorite
Condo in Siesta Key
4.93 out of 5 average rating, 43 reviews

Beach Haven on Siesta Key Beach

ValeryRating, 5 stars3 weeks ago
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.
Guest favorite
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
Condo in Siesta Key
4.92 out of 5 average rating, 195 reviews

Bright and Beachy - Steps to the Water!

LilianRating, 5 stars3 weeks ago
Departamento muy bien equipado hay de todo , también la cocina con básicos , refrigerador con una bebida helada , muy limpio , tal cual lo describen , playa privada , preciosa Gracias
Guest favorite
Condo in Siesta Key
4.95 out of 5 average rating, 76 reviews

Casa Mar Steps 2 Siesta Key, Pool, Tennis, & More!

AlliRating, 5 stars3 weeks ago
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!
Superhost
Condo in Siesta Key
4.86 out of 5 average rating, 79 reviews

Charming Bayfront 2 BRs Siesta Key Condo

ChrisRating, 5 stars3 months ago
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!
Guest favorite
Condo in Sarasota
4.92 out of 5 average rating, 143 reviews

Cottage on Siesta Key Your own getaway!

DeniseRating, 5 stars1 week ago
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.
Guest favorite
Condo in Siesta Key
4.94 out of 5 average rating, 121 reviews

Seaside Sanctuary

GwenaelleRating, 5 stars1 week ago
The place was exactly as described in the listing. The kitchen had everything we needed and overall quiet surroundings. The beach was very close and easily walkable even with children which was a plus! Great place and great location!
Guest favorite
Condo in Siesta Key
4.84 out of 5 average rating, 154 reviews

The Key to a Great Vacation!

FabioRating, 5 stars5 days ago
Somos una familia de 4, el lugar es excelente por donde se lo mire. Pasamos unos dias lncreibles, no solo lo revomendamos, lo volveria a elegir sin dudas. Jennifer siempre muy atenta a nuestras necesidades, un 10 de 10

Family-friendly condo rentals

Guest favorite
Condo in Holmes Beach
4.88 out of 5 average rating, 121 reviews

Steps from the beach

KellieRating, 5 stars2 weeks ago
This condo was perfect for our family. She had everything we needed to make our vacation perfect. We really appreciated the beach chairs, beach towels and beach toys. The condo was very clean! It was perfectly located on a dead-end street, so it was very quiet and peaceful. Centrally located to restaurants and a Publix within walking distance. Just a short walk to the beach! The pool was one of our favorite amenities. Monika’s place made our first trip to Anna Maria amazing and memorable. Thank you, Monika!
Guest favorite
Condo in Siesta Key
4.93 out of 5 average rating, 204 reviews

Steps away from beach and village! #1 in Siesta!

JackieRating, 5 stars2 weeks ago
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.
Guest favorite
Condo in Siesta Key
4.95 out of 5 average rating, 19 reviews

Siesta Key GULF SIDE #100-Peaceful, Private Condo

MarthaRating, 5 stars10 months ago
Renee is an amazing host. When we told her we were flying in Friday night and getting a hotel because the flight was cheaper she offered to let us check in Friday night for no charge. Renee checked in with us a few times throughout the week to see if we needed anything. We look forward to vacationing with her again in the future.
Guest favorite
Condo in St. Pete Beach
4.91 out of 5 average rating, 103 reviews

Comfortable 2BR condo, walk to all sand beach

KarlaRating, 5 stars1 week ago
This condo was in a great location and has a lovely pool that is kept clean and only a few short steps away! Several beaches to choose from in close proximity. The condo was clean and stocked with everything one would need to feel at home! Greg was great and we definitely will rent from him again!
Superhost
Condo in St. Pete Beach
4.88 out of 5 average rating, 149 reviews

Sun, Beach Views, and Smiles!!!

KimRating, 5 stars1 month ago
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!
Superhost
Condo in Sarasota
4.73 out of 5 average rating, 132 reviews

Best Deals on Siesta Key

CarolRating, 5 stars3 weeks ago
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.
Guest favorite
Condo in Siesta Key
4.89 out of 5 average rating, 70 reviews

Beach & Pool Open! Beachfront View Every Room

KellyRating, 5 stars2 months ago
We really enjoyed our stay. This end of the island has its own area for dining and shopping, which seems less hectic and crowded than the village. The beach was beautiful and we felt very secure with the gated community. I really liked the placard for securing beach chairs as well. We would definitely recommend staying here to our friends and families
Guest favorite
Condo in Sarasota
4.86 out of 5 average rating, 105 reviews

5209B Calle Menorca - Siesta Key Village Condo

BarbRating, 5 stars1 month ago
Easy check in. Very close to everything. Pool was a great extra !

Weekly condo rentals

Guest favorite
Condo in Siesta Key
4.88 out of 5 average rating, 50 reviews

Enchanting Coastal Ambiance & Breathtaking Sunsets

LillieRating, 5 stars2 weeks ago
home was very clean and cozy!! everything was in walking distance and close to the beach, restaurants and shops were walkable distance 😊
Guest favorite
Condo in Sarasota
4.89 out of 5 average rating, 55 reviews

Siesta Key Condo, Heated Pool, Newly Renovated

PaulaRating, 5 stars3 months ago
It was a lovely place with so many amenities that made you feel at home! Comfortable beds, nice appliances, great shower pressure, ceiling fans in every room. Lots of towels. The only thing we missed was a lanai but we were A-ok without it!
Guest favorite
Condo in Siesta Key
4.89 out of 5 average rating, 37 reviews

Siesta Key Oceanfront View Condo - unit 407

MatthewRating, 5 stars2 weeks ago
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.
Superhost
Condo in Siesta Key
4.91 out of 5 average rating, 44 reviews

Dreamview Beachfront Romantic/Pet Friendly Getaway

RobinRating, 5 stars3 months ago
Fantastic location on quieter area of beach but still walkable to the Village restaurants. Comfortable bed, huge shower. Loved our stay!
Top guest favorite
Condo in Siesta Key
4.93 out of 5 average rating, 44 reviews

Siesta Oceanview Retreat-1 min walking to beach

ArlonsRating, 5 stars6 days ago
We had a wonderful time at Queen’s Siesta Oceanview Retreat! The location is unbeatable — just a 1-minute walk to the beach, which made it incredibly easy to enjoy the sand and ocean daily, even with a baby. The unit was clean, well-equipped, and very family-friendly. The extra beach chairs, toys, and essentials in the storage unit were a great bonus and much appreciated. Check-in was smooth with clear instructions, and communication with the host was always prompt and friendly. We also appreciated the thoughtful touches like extra linens, towels, and laundry supplies — everything we needed was available. We would absolutely recommend this place to anyone looking for a relaxing and convenient beach getaway. Thank you, Queen, for being a great host!
Superhost
Condo in Siesta Key
4.69 out of 5 average rating, 140 reviews

Siesta Key retreat- 2/1 condo w/pool, beach access

AngelaRating, 5 stars1 month ago
My experience was great from the start. After making my booking I received video instructions, showing how to enter the gate, find the laundry, use the key fob and everything I needed when I arrived. I loved this because it made everything familiar and easy. I also appreciated that when the room was ready we were notified that we could arrive at anytime and aftrrwards we received a follow up to make sure everything was to our liking! we had a great time! Thank you!
Guest favorite
Condo in Siesta Key
4.93 out of 5 average rating, 58 reviews

1 Bed Cottage, Full Remodel, Beach Access #7, Walk

BrianRating, 5 stars1 month ago
Jeff was a great host. Everything went smoothly. Would highly recommend
Top guest favorite
Condo in Siesta Key
4.93 out of 5 average rating, 46 reviews

Siesta Key condo - Gulf and bay club bayside

JohnRating, 5 stars1 month ago
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.

Quick stats about condo rentals in Siesta Key

  • Total rentals

    980 properties

  • Nightly prices starting at

    R1,255 ZAR 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key
  6. Condo rentals