
Holiday rentals with outdoor seating in Sarasota County
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Top-rated Holiday Houses with Outdoor Seating in Sarasota County
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Holiday House Rentals with Outdoor Seating

Peaceful and Cozy place for all of your life needs
Home was just as pictures showed. We love to cook our own meals and kitchen had everything we needed. There were even some spices, coffee filters and a few pantry items. Beds were comfortable. We are picky with our pillows so we did purchase new. The living room seating was a little odd and not sufficient for all in our party to comfortably sit if watching the TV but we spent the majority of our time outside. The outdoor space was very nice. We thoroughly enjoyed the pool, lanai and outdoor dining area. There were pool toys and noodles for our use. The gas grill was an added bonus and we grilled frequently. The park across the street added to our fun and we walked our pup every morning. Saw plenty of Florida wildlife and chatted with many friendly folks. Overall a win for us and would definitely stay again!

Last minute May ,house 2 Mil beach .Pets welcome
Great location, clean and cute. A great size for a large or small group of people

Private back yard. Southgate. 2 bedroom, 2 bath.
We had a wonderful stay at Evona’s house. It was so comfortable & nicely furnished with everything you could need for a relaxing stay. Super comfortable bed & sofa. Kitchen was great - spacious & well equipped. Especially appreciated the kettle being British! Loved the secluded garden & we had our thanksgiving dinner out there. The street was so quiet & next to the house was a pretty walkway which you could take - 10 mins walk to Aldi (supermarket) & the French bakery (highly recommended). Can’t say much about restaurants as we ate in most evenings but downtown is only a short ride away with lots of places to eat. Not a long drive to both Siesta & Lido beaches & Arlington park with its huge swimming pool is a very short drive or 20 mins walk away. We would love to return for thanksgiving next year.

Oasis on Helene
This house was perfect for our family! Clean, homey and had everything we needed. The pool was our favorite part and Carolyn went the extra mile to turn on the heater for us… thank you so much! You can tell that they take pride in having a clean house…. Spotless! We hope to stay here again!

Brand New 4BR: Sleeps 10, 7 min to Siesta Key!
Kathleen thought about everything! She went above and beyond to make sure we had everything we could possibly need during our stay. The property is recently renovated so a lot of things were new. The location was great and the house is located in a nice, quiet neighborhood. One thing to note is that one room has thick curtains instead of a door. It wasn’t a problem for us, but just mentioning it so people are aware. Would definitely consider booking Red Door Siesta again!

Blue Sky Retreat
We had a wonderful 8 days stay at this lovely home. The house was spotless, and the private garden and pool were also very clean and well-maintained. We truly felt at home and enjoyed using the pool whenever we wanted—it was so relaxing. The location was great, with beautiful beaches just a short drive away. We had everything we needed in the house, which made our stay even more comfortable. Our host was incredibly kind, helpful, and responsive. Communication was always quick and smooth. We didn’t experience any issues during our stay. Overall, it was a clean, peaceful, and well-equipped home that gave us a perfect holiday. We’d definitely love to come back again and highly recommend this place to anyone looking for a relaxing getaway!

Pura Vida Near SK
We loved our stay here. Chris was super responsive and flexible with the check in time. The house was only 10 minutes from the beach and all the local restaurants. There is also a Publix less than a mile from the house. We would definitely stay again.

Beautiful Home/King Beds
Very well equipped, clean and close to everything. Loved our stay.
Apartment rentals with outdoor seating

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.

Downtown Apt w/ pool, gym & co-work.
Location is always the key, and Jesse's place its just perfect. 3 Min walk to a delicious French Cafe, restaurants. Excellent parking and I really like the little work station!

Near Siesta Key Beaches - Quiet 1 BR apt
Ed & Bunny’s provided such a wonderful place to stay! My husband and I enjoyed the peaceful atmosphere. Everything was exactly as described and very easy to get to from the Sarasota/Bradenton airport. It was also close to the beach! They are absolutely wonderful hosts and we hope to have an opportunity to stay again!

Pets friendly modern studio 5 mi to Siesta Key
Good location and host was accommodating.

Gillespie On The Park, Walk to Downtown
Dan and Charles place was perfect in every way! We cannot say enough about their place and them! Location couldn’t have been any better. We’ve been coming to Sarasota for 3 years now and this place was at the top of our list.Don't hesitate, book it now!

The Oz Courtyard 2.9 mi beach hot tub, pool
I stayed two nights at this beautiful oasis and it was fantastic. I’m a local but I wanted a little staycation and this is perfect.

Only a Foot of Sunshine Here!
We loved staying in Peter and Pearl's unique and artsy home! They have thought of everything anyone could possibly need for a short or extended stay in one of our favorite places - Sarasota. Their home exceeds above and beyond all expectations of what an Airbnb/VRBO should be. My husband and I would definitely stay here again!

"Safe & Clean" - Key West Suite - Siesta Key Beach
My family enjoyed a week long Spring Break trip and felt very comfortable with the location primarily. This is our fourth year at Siesta Key and it is a safe and family friendly environment. I feel secure in allowing the kids to walk to the village and they know their way around as well. The beach is right across the street which is wonderful. The pool was private and not overly crowded with other guests. The den that is converted to the third bedroom is not very private, however we brought an extension curtain rod and long black out curtains to close off the room. It worked perfectly. My biggest complaint would be the temperature of the condo. The thermostat will not go below 73 degrees and to be honest it tended to get pretty stuffy in the condo. It would have been ideal if the temperature was cooler for our comfort level. Overall, we had a fantastic trip.
Condo rentals with outdoor seating

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
We come to Siesta Key a couple times a year. We usually stay across the street- unmentioned, and for many years felt we needed to find other accommodations. We found this lovely, second story condo so close to the beach, with comfortable , updated, clean amenities. Stay here! We walked in and there was a basket full of fruit, snacks, cold water in the refrigerator. The unit has been nicely updated, clean and comfortable.

No Damage: Cozy 1BR Beach Condo on Siesta Key!
William was a great host and his home had everything we needed for our stay. The distance to the bay and private beach were both perfect and we even got to see a few dolphins in the bay in the morning! We will definitely be back!

Siesta Key Ground Floor Condo 2BR On Trolley Line
This is a great place to stay on Siesta Key. It’s a prime location, provides easy access, close to restaurants/bars/shopping, a short walk to the beach, very clean unit, parking space is right in front of the first floor unit door, nice furniture, great beds, plenty of closet space, good washer & dryer and very responsive owners/hosts. I highly recommend staying at this place on Siesta Key.

Cozy Condo on the Coast!
Me and my boyfriend spent our anniversary here and it was an absolute blast !! 😊 Heidi is the kindest, sweetest soul ever. She made us feel very welcome and was very up to date and was very communicative. The condo was amazing and the beach was beautiful. We loved how peaceful and private it was ! A lot of accommodations were provided and that was veryyyy helpful and stress free !! Everything was super close , beach , stores , town. Will definitely come back for another perfect trip . 🥹♥️

Beachfront - Siesta Key 2 BR walk out to beach
great place to stay...room was clean, very short walk to the beach, many items in the room available to use (numerous beach chairs, beach umbrellas, life jackets, ect) would definitely stay again!

The Key to a Great Vacation!
We had an amazing stay here! The location was everything. Being able to walk across the street and have private beach access was so nice. We saw dolphins every night off the dock. We can’t wait to come back.

Bayside Bliss
We will definitely be back. Such a nice place to stay at. Right on the water. Great pool and great lawn area to watch the boats go by. So close to the beach with all kinds of beach chairs and amenities. The place was very clean neat and updated. I wish we could’ve stayed longer. Thank you so much!

[Beach Retreat] modern condo +5 min. walk to beach
I love the place. You can walk to the beach and the restaurant's.
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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Gulfport Beach Recreation Area
- North Beach
- Coquina Beach
- Vinoy Park
- Manasota Key Beach
- Fort De Soto Park
- Streamsong Resort
- Jannus Live
- River Strand Golf and Country Club
- Myakka River State Park
- North Beach At Fort DeSoto Park
- Weedon Island Preserve
- Alafia River State Park
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