
Holiday rentals with outdoor seating in Osprey
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Top-rated Holiday Houses with Outdoor Seating in Osprey
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Holiday House Rentals with Outdoor Seating

PERFECT FLORIDA GETAWAY !
The hosts were great and communicated very well. They got back to me quickly with questions. The area is beautiful and close to shopping. The perfect place for a quick little get away. Much better than any hotel!

Spacious 2 Bedroom Home | Near Beach | Heated Pool
Melissa's listing was very nice and comfortable. The beds were comfortable and the ceiling fans worked great. The bathrooms were clean and the showers had good water pressure. There was lots to do in Venice and a drive to Sarasota was at most an hour. It was also nice that beach items were supplied, such as chairs, umbrella, coolers, etc. The house was also in a quiet neighborhood and we felt safe at all times. I would definitely recommend to others!

Oceanfront Home with Heated Pool in Fishers Haven
House is immaculate! Super clean and comfortable. Beds and linens were luxurious! Ceiling fans in entry room including the screened in porch. Nice touch! Backyard waterfront is amazing. We used pool and hot tub multiple times per day. We fished off the dock and caught a few catfish. Sergiy was a perfect host. Excellent communication and direction when needed. Highly recommend!

Bayview House - Osprey - 1 block to Bay!
Excellent location,big house,everything you need is stay with kids,awesome owner!

Coastal 3BR Getaway|5 Min to Beach|Pool+Peloton
This place was great. It had everything a family could need. It was peaceful and quiet and so much space! We loved it.

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!

The Lovely Place Getaway-SRQ
It was a great experience. We were there for the rowing national competition. It is an easy drive to the park, and a nice residential neighborhood. The apartment is well equipped and very clean. I highly recommend!

Cozy & Beautiful Pool Villa in Sarasota County, FL
I stayed at Vera’s house for a week and had an amazing experience from start to finish. The place was exactly as described—clean, spacious, and well-equipped with everything I needed for a comfortable stay. The neighborhood was peaceful and safe, with easy access to shops and local attractions. The host was incredibly responsive and helpful, making check-in and check-out smooth and stress-free. I especially appreciated the thoughtful touches around the home. Highly recommend this host to anyone looking for a relaxing and hassle-free stay. I’d definitely book again!
Apartment rentals with outdoor seating

*Recently Updated* Cozy Oasis, centrally located
Christina was such a sweetheart. She was very kind, accommodating, and giving. I would stay here 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.

VILLA 5 · Pool view. King bed. Daily rentals
process was very simple to check in and check out. David was very polite , the place was very clean it was accommodating with basic supplies such as dishes silverware coffee maker even have some coffee , paper plates simple necessities, shampoo , conditioner some soaps , towels, chairs and cooler, floats for the beach that's within walking distance the neighborhood is beautiful, definitely a little piece of paradise I'll definitely come back.

Near Siesta Key Beaches - Quiet 1 BR apt
Ed and Bunny’s place was very clean and private. The neighborhood is quiet and only 10 minutes from Siesta Key which was our main location to visit on the trip. They provided beach chairs and towels for beach goers and left a note for recommendations.

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.

Pets friendly modern studio 5 mi to Siesta Key
This place was exactly what I was looking for! Very comfy with everything I needed, and in the neighborhood where my friend lived. Yelena was very quick to respond to communications. Would definitely stay here again.

Only a Foot of Sunshine Here!
Peter and Pearl are awesome hosts! The Peaceful Retreat feels welcoming and cheerful, with very comfortable furnishings. These hosts have thought of everything! The location is great too, whether you walk or drive. We were in Sarasota to attend graduation at RCAD and the location was perfect!
Condo rentals with outdoor seating

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
thank you so much for allowing us the pleasure of staying in your beautiful condo. You have thought of every amenity any one could want!

On the Beach; Siesta Key SunBum Studio
My daughter and I stayed for a mother daughter girls trip and had a blast! They made sure to take care of every little detail to make you feel comfortable and at home. Even checking in and making sure we made it ok. It was very clean and the location was amazing. Easy to get around on the trolly if we didn't want to drive and literally steps away from the beautiful white sand and clear turquoise beach. Do yourself a favor and book the trip!

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

A&A's Paradise near IMG & Anna Maria beaches
This was the most clean, most relaxing, most safe feeling place we've ever stayed in through Airbnb!! Thank you so much for such a wonderful experience. We would recommend 10/10 to anyone!!!!

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!
Five stars in every way. Location location location, everything is very close and convenient including the free shuttle that goes up and down the island. The home itself is extremely clean, the bed is comfortable, and the place is stocked with chairs, umbrellas, towels, anything you need. You do need to take some stairs to get to the unit, but if you’re comfortable with that pick this place. I reached out to Martha several times with questions about the island and she responded very quickly and was helpful every time.

Anchor house +6 min. from Siesta Beach+heated pool
If you are looking for a place in Sarasota with everything you need closed to you like restaurants, dinner, food shopping etc at just minutes from siesta key then this is the place. Very clean and definitely what you see in pictures is what you getting. I stay here with m wife and two kids, we are very happy with pick this place, will definitely book again.

Charming and Updated 1 Bedroom in Runaway Bay
My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!
Quick stats about holiday rentals with outdoor seating in Osprey
Total rentals
40 properties
Nightly prices starting at
$93 AUD 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
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- North Beach At Fort DeSoto Park
- River Strand Golf and Country Club
- Myakka River State Park
- Alafia River State Park
- North Jetty Beach