
Holiday rentals with outdoor seating in Osprey
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Top-rated rentals with outdoor seating in Osprey
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Popular amenities for outdoor seating rentals in Osprey
House rentals with outdoor seating

Perfect location updated & loaded with all u need!
Would recommend highly! Great location (everything is working a 10-15 min drive at the most). The place itself is very cozy and plenty of space for the four of us that resided there for the weekend. Definitely would stay here again if I find myself in the area again.

Adorable Bungalow Fire pit/outdoor shower 2/1 Cute
We would definitely stay here again. This is a lovely little bungalow. The place is very accommodating, clean, safe and inviting. Our host Jackie made sure we had everything we needed and the instructions were very simple and clear for the home. No complaints.

Bayview House - Osprey - 1 block to Bay!
We LOVED staying at Valerie’s place! We were comfortable the moment we stepped in. It’s open, bright and beautifully furnished. We spent a lot of time enjoying the deck that fully opens onto the living room. The house was equipped with everything we needed, including beach chairs, towels, bags and cooler. It was spotless! The beds and bedrooms were quite comfortable. The guest room with a single bed and trundle was perfect for our two grandchildren. We really appreciated being able to walk down the street to a great restaurant and tiki bar plus a very walkable neighborhood. Its location is near to shopping and central to numerous beaches: Siesta Key, Lido, Venice and Nokomis; St. Armonds Circle; The Ringling; and many other attractions. Valerie was a great host-responsive and easy to communicate with. We enjoyed her home so much that we booked it for a future stay.

Spectacular Sunsets! 15 min Siesta Key!
We loved the villa and would gladly stay here again. The community was wonderful, and the location provided ready access to everything that we wanted to see during our stay. The host was responsive to every question. We were very thankful that we found this home!

The Nautilus Hacienda
Very cute, very "guest-based" (many touches throughout the home to welcome and guide), & very close to Nokomis Beach - I had a wonderful week.

Summer sunset. 3 minutes away from beach!
Very responsive and accommodating host! The house is very close to the beach and other local attractions. We enjoyed our short stay. Great value.

Stunning Luxe Casita- Gateway to Siesta Beach
We stayed a wonderful 2 nights in Cynthia and Neal’s Casita and we already can’t wait to be back! The home has everything you may need for an amazing beach vacation. Cynthia and Neal really thought of everything and you can tell that they put a lot of love into what they do. We will definitely be back! Thank you again Cynthia and Neal!

Acacia Haven
The house was perfect! Just as described and a great layout for a large family. The amenities were awesome especially the outdoor space with the pool and spa and outdoor TV. Very kid friendly with toys and crib and highchair. Would definitely recommend 10 out of 10!
Apartment rentals with outdoor seating

*Recently Updated* Cozy Oasis, centrally located
Quiet, cozy and comfortable. If you love plants, you will enjoy her gardens- they are beautiful! She thought of everything I might need and even provided things I didn’t know I needed. I would definitely book there again!

Free Early Chk-in, Super Clean, Free Parking,Bikes
We had a great stay at Lisa’s. It was well stocked and had everything we needed for a great stay. Would definitely recommend!

Cozy and Private Studio Near Downtown & Beaches
This location is halfway between coastal attractions (beach and downtown) and inland attractions (golf, Lakewood Ranch, I-75). It's also near 2-3 east-west roads in Sarasota. Excellent. Listing is realistic, not exaggerated. It's a well-equipped kitchen with a two-burner induction stove and a large enough fridge and freezer for nearly any purpose. Good counter space and many helpful supplies and "tools" Bedroom area is large, bathroom is huge, shower is enormous, access is ez. I've stayed in tiny units and i've had faux kitchens. This is neither and with a strong host nearby. I'm tiring of long-distance hosts and corporate hosts. As a host Mariele offers proximity, professionalism, and personality too. Within reason she's on the side of the guest. Recommended listing.

Gillespie On The Park, Walk to Downtown
We (two people from Germany) stayed here for a week, not for the first time – great location: close to Siesta Key, Lido Beach, and downtown; beautiful accommodation – very lovingly and beautifully furnished, we felt like we were at a friend's house; we had everything we needed, even all the beach equipment; Dan and Charles are great hosts. We would like to come back.

VILLA 5 · Pool view. King bed. Daily rentals
Great place close to the beach and refreshing pool! Enjoyed great meals at Captain Curt’s and Mango Cafe only 10 minute walk away. 7Eleven was close by and handy for beach snacks. Beach chairs provided were much appreciated. Met nice fellow travelers while enjoying morning coffee by the pool. All new interiors had all we needed.

Near Siesta Key Beaches - Quiet 1 BR apt
Ed and Bunny were communicative and friendly hosts. Inside of the efficiency, space is as the photos (I even think the magazines are set up the same way haha). Very well organized and neat. Nice little pathway on the side of the home that separates the spot from the rest of the home and adds a touch of privacy. Spot is in a nice and quiet area and what it looked like a safe neighborhood. 10 mins from Siesta Beach. ✅.

Old Florida-Style Spacious Studio w/ Full Kitchen
It was a great stay! The place was very cute and super close to siesta key downtown and Sarasota! They were super responsive and helpful when we needed

Modern Private Apartment 1 Block from Sarasota Bay
Outstanding host and place, definitely will book it again. Perfect location, peaceful environment. One block from ocean.
Apartment rentals with outdoor seating

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
My husband and I really enjoyed our vacation at the wonderful apartment of Lauren and Mario, the place is so clean and cozy. Also, few minutes away from the beach and we drove few times to South Lido Key Beach Park which was so quiet and clean (highly recommend). We definitely will come back 💕

Sea Shell Ocean view On Beach Walk everywhere Pool
Amy is an extremely thoughtful and responsive host that clearly exhibits what Airbnb is meant to be. Her place in Siesta Key is right on the beach with perfect amenities and easy access. My friends and I have been vacationing in Siesta Key for almost a decade and this is by far one of the best places we have stayed. Thank you Amy!

LIDO KEY 1 BR/1Bath Heated Pool 16
Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed

Siesta Key Ground Floor Condo 2BR On Trolley Line
Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
My husband and I really enjoyed our stay at Martha’s cute and cozy condo. The view was the best part. Love being on the beach and even though the weather wasn’t the greatest, Martha had wonderful books and games for us to use. Another shout out to Martha is that we forgot my husband‘s favorite backpack cooler yet Martha took a picture of it and said she would hold it until our next visit which I thought was very honest and considerate. Thank you again and hope to see you soon! J&R T.

Condo with a View 1: Beachfront!
Fell in love with this place as soon as I walked in! So peaceful, so beautiful 😍😍 absolutely loved my stay!

Siesta Key Beach Front Condo
Our stay was exactly what we wanted. Our host, Evan, was great and quick with any questions we had. The condo was located very close to Siesta Key Beach, and we didn't have to drive more than 20 minutes to get to anything that we wanted to around that area, some things even within walking distance. Everything we could have possibly wanted was provided in our home, which really made the week stress-free. We would definitely stay here again!

NO Stairs, beachfront & short walk to the village!
We had a fantastic stay! The apartment was very well-equipped with everything—and more—that our family needed for a perfect beach vacation. We absolutely loved the location, especially being able to walk barefoot from the house straight onto the beautiful sands of Siesta Key Beach. It made everything so easy and relaxing. Highly recommended—we’ll definitely be back
Quick stats about holiday rentals with outdoor seating in Osprey
Total rentals
40 properties
Nightly prices starting at
₹5,138 before taxes and fees
Total number of reviews
980 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
20 properties have a pool
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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
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Jannus Live
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Myakka River State Park
- Alafia River State Park
- South Jetty Beach