
Waterfront vacation rentals in Siesta Key
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Top-rated waterfront rentals in Siesta Key
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Waterfront apartment rentals

Newly Remodeled Beachfront Studio - On the sand!
We LOVED our stay at One Shell Cove, and hope to be back! You couldn't ask for a more beautiful location or view. The kitchen was so well-appointed that we chose to buy fresh shrimp and grouper and eat outside while listening to the waves crash. The entire condo was spotless, and the king bed was comfortable. We used the beach chairs provided and swam in the perfect Gulf waters. The condo is walking distance from a Circle K and several restaurants. Although it's on a public beach, the area was quiet and peaceful and we were not disturbed. I would highly recommend this condo and its wonderful Host!

Condo Kokomo - stay ON the beach in Siesta Key!
The condo is directly across the street from the beach and within walking distance of the restaurants and shops. It has a great little patio that we sat on to eat breakfast and to enjoy an evening cocktail. There is a closet with beach chairs, umbrellas, sand toys and coolers and Amelia provided beach towels. It was perfect!

King bed. Pool. Daily rentals
this is my second year in a row coming down to siesta key and I have always stayed here. walking distance from everything but yet this place is quiet and peaceful. it is a diamond in the ruff.

Las Palmas Beach Rentals Unit 1
Cute as a button! Super homie! Steps to the beach! Had everything we needed. The place was just as described and walkable to almost everything. Great location! Fabulous house! We will definitely be coming back to stay with Debra. The sunroom is absolutely the best spot in the house!

Steps from Upham Beach & Pool
For two teachers with two young kids wanting to get a beach break to start summer vacation this was the perfect place. It is a quaint space but we had everything we needed and the location and amenities were fabulous. Being able to walk to the beach and having a nice pool was a huge reason why we booked the it and it exceeded our expectations. When we arrived there was sand in the bed and the shower was not cleaned but it was fixed the next day, and when we tried to use the beach umbrella and it was broken, a new one was brought later that day. Kristen is quick to respond, we thoroughly enjoyed our stay, and we would stay there again.

Longboat Key-OCEAN FRONT- on the beach
Absolutely loved our stay! The place was spotless, beautifully decorated, and had everything we needed for a relaxing getaway. The location was perfect—just steps from the beach with stunning views and peaceful surroundings. Cindy was incredibly responsive and welcoming. We’ll definitely be back—highly recommend

Serenity on the Manatee
My husband and I stayed two nights at Serenity of the Manatee. We really enjoyed this beautiful, peaceful, and cozy place that is only 30 to 35 minutes from beaches. The place was clean, comfortable, and had everything we needed; however, a small stove will be a great addition for longer stays. We would definitely stay here again.

Dream Boat at The Beach Dreams Resort
Everything was great, perfect location and perfect space for the two of us for our getaway. Air conditioning worked well in bedroom and living room/main area (I think some people previously commented on it being hot & the entry area is warm and not directly air conditioned, but the unit had several fans in the closet). We didn’t find this to be a problem at all for us. Everything was clean and as described in the listing. The only “complaints” if you could even call them that was that the WiFi did not seem to work no matter what we did and the water pressure wasn’t ideal for my husband, yet didn’t bother me too much so maybe that’s subjective. Overall, the owners were very accurate with what was offered and received, and they were very responsive as well, answering any questions we had very quickly, and calling us when we had a small issue with parking at first when we got there. They were friendly and asked how everything was going during our trip and we appreciated that very much.
Waterfront house rentals

The Shore House Private Dock Hot Tub
Great house. We had a wonderful time. Jenni and Ritchie are very friendly. Highly recommend it!

Coastal Retreat near Siesta Key Beach and Downtown
Aubrey’s place is amazing! It’s in a great location close to the best attractions Sarasota has to offer, but you’ll find yourself just wanting to stay inside and enjoy this masterfully decorated space. I cannot exaggerate the fact that it feels like you are stepping into a page in an interior design magazine. Aubrey herself was delightful to communicate with. She left us a very sweet welcome note and little gift. Wish she had a bnb in every town we visit!

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

Spacious & Modern Gem ~ Walk to Gated Beach ~ Pool
We are a wonderful stay in Siesta Key! The place was amazing and perfect for our extended family vacation. Plenty of room for everyone!

Lake Front House with a Pool
This house was spotless, organized and had a loaded kitchen! It is in a amazing location near the beaches and the house came loaded with beach equipment. I would love to come back. Birute was very helpful with us and responsive in timely manner Thansk for all!

Rustic Sands - 650
Our time at this Airbnb in Siesta Key was amazing! The house was super clean and had an awesome kitchen with everything you could think of, plus more. Great appliances, tons of towels, dishes, some games, TVs with premium channels and more! Outside was just as great. The pool area was covered with mosquito netting, so we could relax without bugs bothering us. The pool was our favorite spot! super clean, and the outdoor BBQ grill was great! The only thing was the master bedroom bed was a bit small and not the most comfortable for us (queen size), but everything else was so good. The neighborhood was really quiet, location was 4 minute drive from the beach. Overall, this Airbnb was one of the best places we've stayed. I would 100% recommend it and would come back! it looks better in real life than the photos.

Sea Club II Garden House
This location was perfect- we could walk to the beach and have a short trip to local restaurants and grocery stores. This beach is spectacular, and the most beautiful I’ve experienced. The house was everything we could ask for - very clean and the rooms and furniture are comfortable. The pool is a nice add though we didn’t use it- we were at the beach instead. We didn’t need to contact Richard as everything was as expected and explained. Thank you so much!

True Island Living House/beach/water views
This was among the most beautiful and well-appointed Airbnbs that we’ve had the pleasure of staying in! Our trip was centered around a family 60th birthday celebration and this was such a lovely backdrop for our gathering. Our primary plans were to enjoy the sunrises and gorgeous outdoor area, cooking meals on the grill and enjoying them by the pool with a view of the intercoastal waterway. As such, when we arrived to find that the grill wasn’t working properly, we were disappointed. We communicated with our host about the grill the day after our arrival, and received an immediate response. However, it ultimately required back and forth texts (some at our initiation due to not receiving an update) and three days until the handyman graciously brought over his grill to loan us. Something we learned from this trip is the importance of communicating to your hosts what it is about their place that is most important to your stay—and perhaps we should have checked on the grill specifically.
Waterfront condo rentals

Siesta Key Beach front 2 bedroom condo w/ parking
Everything was as described, location is perfect right across Siesta Beach. Restaurants / shops were a short drive away, which was preferable for us traveling with a 5 & 8 year old (did not want to be in middle of chaos). Condo is modern, had everything we needed (including beach toys for kids which was not really expected). Instructions were spot on, did not reach out to Geoff until 2nd to last day of our stay and when I did I got a response back in minutes. Would definitely recommend this rental, it was our first time to Siesta Key, we fell in love with place and plan to be back soon. Geoff was a gracious host, you could tell he wants guests to feel at home & has done a great job accomplishing that

2 BR condo in Siesta Key w/ Private beach access
The location was outstanding for walking to beach and restaurants. The unit had all the beach equipment we needed and it’s right on a trolly route to take to the village. I would definitely stay there again

Penthouse Expansive Ocean Views
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.

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.

Dreamview Beachfront Romantic/Pet Friendly Getaway
Fantastic location on quieter area of beach but still walkable to the Village restaurants. Comfortable bed, huge shower. Loved our stay!

Siesta Dunes 1st Floor Beach Front Retreat + Bikes
We have been coming to Siesta for years and rented all over the key. Siesta Dunes is right on the beachfront. It’s large with a huge pool in the centre with tons of loungers and umbrellas and then you walk out to the massive beach. Although people say walkable to the beach, in most cases you have to cross the main road and go to the other side which is a severe pain. This is all contained and it’s important for me to have the least work possible on vacation. There’s a centre deck with bbqs overlooking the beach where everyone comes to watch the sunset. Tanya’s place is bigger than it looks on the photos with two back decks, plenty of seating inside and back out. Siesta is our home twice a year and now that we found Siesta Dunes we are booked for Christmas. The trolley is the best part of Siesta outside of the massive white beach and we always make a date night at Summer House. Tanya’s is worth staying at.

Sarasota Surf & Racquet Club Siesta Key Condo
This was an amazing condo for our family trip! Pictures and listing were very accurate and it was so lucky to find a property on Siesta Key that was actually on the beach. We would absolutely stay here again! The beach is stunning and the two pools are wonderfully maintained Some things worth mentioning (they are disclosed in the listing) - you must provide your own beach/pool towels but there are plenty of shopping options nearby - beach chairs are free and located once you get down to the beach - for a fee, you can reserve/rent an umbrella and have it set up for you during your stay. The guys are out there early (7-7:30am) but then come in around lunch time so if you want an umbrella, I suggest going out in the morning to get it setup - dish soap, dishwasher tablets, hand soap are provided but you’ll need to purchase everything else (salt/pepper, spices, oil, ziplocks, shampoo/conditioner, etc). Super central location and very secure property! Would definitely stay here again!

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!
Quick stats about waterfront rentals in Siesta Key
Total rentals
350 properties
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Total number of reviews
10K reviews
Family-friendly rentals
290 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
290 properties have a pool
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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
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- River Strand Golf and Country Club