
Townhouse holiday rentals in Siesta Key
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Top-rated townhouse rentals in Siesta Key
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Popular amenities for Siesta Key townhouses
Family-Friendly townhouses

Gulf and Beach Views-Steps from Beach and Village
Definitely meet our expectations and more, beautiful home. We felt at home. Very clean and perfect location. Will return for sure!!!

Walk to Beach & Village, Heated Pool Oasis
This was the best B&B We have stayed at thus far. Super clean & it felt like home. It is one block from the grocery store, many, many restaurants, ice cream shops & shopping! The beach is a five minute walk & it’s a beautiful upscale neighborhood. There was a little farmers/market across from the grocery store & liquor store on Sunday. We felt super safe and comfortable everywhere we went. We ate at four of the restaurants and they were all very good. The pool was a nice bonus & we will definitely book here again! I’m giving this B&B 5 stars *****

Our American Dream - A Paradise Destination
I visited to take care of a parent going into assisted living. Everything was comfortable, easy, clean and beautiful! I especially loved rising early and walking the neighborhood...the sandhill cranes, landscaping and lake were all beautiful!

Anna Maria Island TH - close to beach, pool!
We had a wonderful stay at this townhouse. It was located close to everything. The place itself, had everything we could want! It was super clean and very comfortable! We would most definitely stay here again, and are already planning for our future trip! Thank you again, Sean!

Thanksgiving Availability! 1/2 Block-Beach Access
This was the perfect beach house getaway for my family. The house was well stocked with everything you would need in the kitchen, bathrooms, bedrooms, and even pool/beach supplies. The beach was only short walk across the street. The pool was amazing and probably our favorite spot to hangout. Will definitely look into booking Anna’s place again because it’s a gem!

Townhouse 200 Steps to the Beach
Great place, great location and good amenities. We had fun.

River Strand Holiday
The house was really nice and clean. The house was more spacious than we expected from the pictures. Plenty of room for bigger group. Area was nice and quiet. Landlady Darina and Simona at the site were really helpful and responded immediately if any questions came up. I would highly recommed this place.

Home w/Private Pool and Game Room-Island Time East
Our stay was comfortable and convenient. The home was well appointed with all the necessities. We would stay there again when visiting siesta key.
Townhouse rentals with a washing machine and dryer

Bradenton Townhome - Walk to Locals-Only Beach!
The place was lovely. We enjoyed our stay. The place was clean and well stocked. Short walk to the beach. We would definitely stay again.

Modern Sunshine Oasis Just 20 mins to Siesta Key!
Great stay host was friendly and responsive. Would stay again nice and quiet.

Near Beaches, Huge heated pool, walk to shops
We were in town for an event at Nathan Benderson Park and this was a great place for our home base. The place was cute, spotless and well-stocked. Catherine was extremely responsive to questions and made sure we had what we need. She even contacted me right away when the wi-fi was out - before I even noticed. And we appreciated the card and welcome snacks and wine! The area was very quiet and an easy drive to everything.

Canal Lower-Gorgeous 3 bed 3 bath near SK Village
Everything was amazing!

Luxe 3BR Near Downtown | Elevator & Rooftop
This was a fantastic Airbnb experience. Photos and descriptions were accurate, and the unit felt very new and clean. Plenty of room for us to stretch out, a kitchen I actually enjoyed using and gorgeous bathrooms. A/C worked very well and the attached garage was extra convenient. Good WiFi. We were in town for a rowing event at Nathan Benderson Park and this location was perfect - easy access to the venue and also very close to restaurants, grocery stores and beaches. Our friends stayed in another unit in this development, which made the stay even more convenient. The vacation rental manager SkyRun was extremely professional, responsive and helpful. We couldn’t have asked for more. Thanks!

Hidden Gem. Near downtown and beach
The Hidden Gem was perfect for our family of five and our vacation! The location, the pool, the amenities that Jonathan and his wife provided…made it hard for us to leave. We had three younger children which loved the pool, but also spent our days at various beaches, islands, and Keys. The Ringling Museum was phenomenal also! Great restaurant recs (we went to Origin, rooftop at Ovation Hotel for sunset, Cask &Ale!). The primary bedroom and master bathroom is just beautiful. Thank you for a wonderful stay!

Light & airy townhome, beach & bay views from deck
Loved this place. Location was great with easy access to the beach and the pool. Beautiful and well maintained home. Well appointed, clean and comfortable. Plenty of useful supplies to enjoy beach toys, towels, chairs, etc. kitchen is well equipped. Our kids enjoyed the puzzles and games at home. Chelsea and Ben were a wonderful host with excellent communication!

Family Friendly, 1/2 Mile to Siesta Key Beach.
My husband, mom, and I stayed at Rob’s beautiful home for a week. From the moment we arrived it felt like home. We felt safe and the entire home was spotless. There was plenty of room for all three of us and what I liked most was the privacy of the master bedroom. The bathroom was excellent after long beach days. I really enjoyed being able to take a relaxing bath in the bathtub which felt like luxury. The kitchen came with everything we needed in order to feel like the home was really ours for the week. Rob also provided so many different things for our daily beach trips including a beach wagon. This really helped save our backs as we like to pack for full beach days. The living room space felt cozy for movie nights. I really want to highlight Rob’s kindness. From the beginning he was very responsive and answered all my questions and gave splendid recommendations. He was also helpful, kind, and understanding on the day of check out with a mistake we made. We truly recommend!
Townhouses with a patio

Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse
We spend a wonderful week at Laura's listing. The apartment was modern, clean, quiet and well furnished with all the necessaries. Laura was incredibly helpful and fast to respond with any questions we had before and during our stay. I would highly recommend this apartment for a beach holiday in sunny Florida!

2 Bedroom Townhouse with Private Beach Access
The home was beautiful and just a quick walk to the beach. The host responded quickly and made sure all our needs were met. Will definitely reserve again.

Getaway Family Beach Townhome w/Pool!
This was a great vacation for my family, including two boys ages 10 and 12. Anna Maria Island is a wonderful place! We loved all the local restaurants. The location is perfect right in the middle of the island . We were close to the beach and free the trolley is right out front. We absolutely loved the bagel place next-door and having a grocery store so close. It was nice to have two bathrooms and the boys had their own room to hang out in. The space was clean and the pool was also a nice amenity. Communication with the host was great! We would come back.

PVTE HTD POOL by Anna Maria *Point Breaks*
Beautiful garden and pool at the exact right temperature. This is a very spacious and comfortable apartment on a quiet cul-de-sac. The kitchen has everything you need. Communication with the property manager is easy and pleasant. 5-10 minute drive to beautiful beaches. Plenty of restaurants within 10 minutes. Excellent value for the price! We would happily return in the future.

Bright & Modern - Sarasota Home
We loved this place! Such a perfect townhome for our family of four, perfectly located off Lockwood Ridge. Groceries within 5min, as well as restaurants, coffee etc. The house had everything we needed, well organized and very clean. There’s a large staircase to the bedrooms upstairs, in case that’s a consideration for some with luggage up the stairs, but for us it was perfect. Thank you for a wonderful week stay!

Charming Lido Beach Condo
We had a great time in Lido Beach. The listing photos were good and we found everything as promised, plus. Mario was helpful.

Nautic Star - Large pool & Free boat dock & kayaks
Larisas place was cozy and beautiful! The place was clean and well equipped. Shops and stores are just 5-10 mins away. There is also a lot of activities nearby so there is plenty to do!

Updated Townhome, Secluded Beach + Pool
Amanda’s place was perfect for our family of four! The condo is located within Cedars East tennis resort and we enjoyed the atmosphere and amenities. The complex features accessible walking paths through the mangroves to a beautiful view of the bay. We paid a small fee for use of the bikes, fitness center, and pool access, all of which were used by our family. The front desk attendant was also very kind and helpful. You are a quick bike ride or walk away from great dining options (Harry’s or Blue Dolphin for breakfast and Lazy Lobster for dinner). The condo is a 5 minute walk to the beach with a crosswalk available. There were additional amenities such as a nice beach cart, beach chairs, beach towels, sand and pool toys, etc that really make this a gem for those traveling by plane. The beds were also quite comfortable Amanda was a responsive and helpful host. Can’t recommend this place enough!
Quick stats about townhouse rentals in Siesta Key
Total rentals
60 properties
Nightly prices starting at
$252 NZD before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
50 properties have a pool
Destinations to explore
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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