
Vacation rentals with outdoor seating in Osprey
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Top-rated outdoor seating rentals in Osprey
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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!

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.

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.

Lake View, 6 Miles From Beach
This place is amazing!!! Jay (the host) was super responsive and helpful. The house is gorgeous with all of the amenities you could want including kayaks, fishing poles (there's a lake in your backyard), towels, beach chairs, coolers, etc. The house is in a gated community with a beautiful zero entry infinity pool (heated) that my boys really enjoyed. There's 3 bedrooms with plenty of space for a large family. I really can't say enough about this house. We will be back next year!

The Nautilus Hacienda
The house is cute and well located in terms of getting to Sarasota or Venice. It is about 30 minutes from the Sarasota airport, but a direct route and so easy to get back and forth. They were very flexible when we needed early check in/late out. There are 2 chairs for the beach, a cooler, towels. We went to the Nokomis beach, which is fairly close and just beautiful. The Master BR has 2 French doors on either side of the room, leading to the LR. The Master BR toilet/shower area is separated from the sink by a louvered folding door. Each BR has a ceiling fan, which was helpful at night! The kitchen is well stocked, there is a nice coffee area with a Keurig coffee maker. There's a great screened porch, which we loved. Great parking.

Summer sunset. 3 minutes away from beach!
This place was fantastic to stay at. All of the rooms were clean, it had a fully stocked kitchen, and a very relaxing atmosphere on the back patio! The host is extremely nice and very accommodating, I will 100% choosing this place for future stays!
Apartment rentals with outdoor seating

*Recently Updated* Cozy Oasis, centrally located
This was a perfect place to stay for my wife and I. It was a short drive to Siesta Keys and downtown Sarasota. I couldn’t ask for a better host or better location. 1000% recommend!

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.

Old Florida-Style Spacious Studio w/ Full Kitchen
Great location in Sarasota! The apartment was comfortable and very clean, and just a few minutes' drive to beautiful beaches and restaurants. Vanessa and Nicole were very responsive and gave us helpful instructions. We would definitely stay here again!

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.

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.

Near Siesta Key Beaches - Quiet 1 BR apt
This was a very cute little place with a beachy chic charm. Ed and Bunny were really welcoming and checked in via the app to make sure we had everything we needed during our stay. Ed even brought us delicious mangos from their tree! Even though the place was connected to their house it felt private and quiet. Im addition, the beautiful tropical plants and lizards scurrying along the path made it feel like a little exotic oasis in the city. We really enjoyed the stay and would love to visit again.

ROYS PLACE Romantic, Private, Paradise!
Roy’s place was comfortable, had good amenities, good location ( multiple beaches and restaurants in a close radius). The house was beautiful and just as described. The pool/hot tub, and outdoor seating was private and well maintained. Chairs, umbrella, and cooler were available to use which was a nice plus. We would definitely love to stay at this place again. Roy was quick to respond to any questions we had.
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!

Sea Shell Ocean view On Beach Walk everywhere Pool
Loved the location and the layout of the condominium! We will be coming back!

Crystal House on Siesta Key Beach
We loooved it here! The space was perfect for our family. I cooked several meals and the kitchen had everything I needed. The location was convenient to grocery stores and walking distance to local restaurants and ice cream shops. The trolley stop is right at the resort so very convenient free rides to downtown Siesta Key was one of the highlights of our trip. We also grilled in the back of the resort by the bay which was nice! Oak trees all around. The pool was perfect temp. The fob didn’t work for one of the gates but there were three others we were able to get in without issue. The beds and pillows were soooo comfy. The ONLY issue we had was from the pics on the original post it appeared the walk to the closest public beach access was 2 min but it was actually 15. In the Florida heat that was rough but we pushed through! Oh and last thing, the scooters were a hit with everyone in our family. So much fun! 😆 Thank you so much for giving us an amazing stay!!

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

★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.

Condo with a View 1: Open Friday, $250/nt!
This condo was everything I needed and more! The location? Absolutely perfect—the beach is literally your backyard. Waking up to that ocean view the next morning was a dream. Restaurants and activities were just minutes away, which made everything so easy and fun. Heidi, the host, went above and beyond. Her communication was fast, kind, and incredibly thoughtful. She even surprised us with a delicious key lime pie and orange juice waiting for us after jet skiing—such a sweet and personal touch! I truly have no complaints. Everything about this stay was peaceful, beautiful, and seamless. I’d absolutely recommend this spot to anyone looking for a relaxing and magical beach getaway. 🌴🌊💛

Siesta Key Beach Front Condo
Another wonderful trip to Siesta! This is our third stay in one of Evan’s places, and we were not disappointed. This unit had a great view of the Gulf (this particular building has the most direct view, without the parking lot!), and the screened in lanai was amazing! As always, the unit was clean, well-stocked, and a perfect home away from home. Already counting down the days till we return!

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 vacation rentals with outdoor seating in Osprey
Total rentals
40 properties
Nightly prices starting at
R1,070 ZAR 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