Holiday rentals with outdoor seating in Osprey

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Popular amenities for outdoor seating rentals in Osprey

House rentals with outdoor seating

Guest favourite
Home in Nokomis
4.88 out of 5 average rating, 26 reviews

Perfect location updated & loaded with all u need!

AleishaRating, 5 stars2 weeks ago
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.
Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 173 reviews

Adorable Bungalow Fire pit/outdoor shower 2/1 Cute

SethRating, 5 stars4 days ago
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.
Superhost
Home in Osprey
4.98 out of 5 average rating, 45 reviews

Bayview House - Osprey - 1 block to Bay!

KimRating, 5 stars2 months ago
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.
Guest favourite
Home in Sarasota
4.92 out of 5 average rating, 101 reviews

Spectacular Sunsets! 15 min Siesta Key!

ToddRating, 5 stars1 month ago
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!
Top guest favourite
Home in Nokomis
5 out of 5 average rating, 19 reviews

The Nautilus Hacienda

BarbRating, 5 stars2 weeks ago
Very cute, very "guest-based" (many touches throughout the home to welcome and guide), & very close to Nokomis Beach - I had a wonderful week.
Guest favourite
Home in Nokomis
4.98 out of 5 average rating, 42 reviews

Summer sunset. 3 minutes away from beach!

CaseyRating, 5 stars1 week ago
Very responsive and accommodating host! The house is very close to the beach and other local attractions. We enjoyed our short stay. Great value.
Top guest favourite
Home in Sarasota
5 out of 5 average rating, 335 reviews

Stunning Luxe Casita- Gateway to Siesta Beach

BarbaraRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Nokomis
5 out of 5 average rating, 12 reviews

Acacia Haven

Elizabeth UpdikeRating, 5 stars1 month ago
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

Top guest favourite
Flat in Sarasota
4.99 out of 5 average rating, 122 reviews

*Recently Updated* Cozy Oasis, centrally located

WendyRating, 5 stars3 days ago
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!
Guest favourite
Flat in Indian Beach-Sapphire Shores
4.96 out of 5 average rating, 140 reviews

Free Early Chk-in, Super Clean, Free Parking,Bikes

VictoriaRating, 5 stars1 week ago
We had a great stay at Lisa’s. It was well stocked and had everything we needed for a great stay. Would definitely recommend!
Guest favourite
Flat in Sarasota
4.79 out of 5 average rating, 103 reviews

Cozy and Private Studio Near Downtown & Beaches

RogerRating, 5 stars2 weeks ago
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.
Guest favourite
Flat in Gillespie Park
4.97 out of 5 average rating, 172 reviews

Gillespie On The Park, Walk to Downtown

JuliaRating, 5 stars1 month ago
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.
Guest favourite
Flat in Sarasota
4.84 out of 5 average rating, 238 reviews

VILLA 5 · Pool view. King bed. Daily rentals

BruceRating, 5 stars4 days ago
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.
Top guest favourite
Flat in Sarasota
4.98 out of 5 average rating, 177 reviews

Near Siesta Key Beaches - Quiet 1 BR apt

HeliodoroRating, 5 stars2 weeks ago
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. ✅.
Superhost
Flat in Sarasota
4.82 out of 5 average rating, 134 reviews

Old Florida-Style Spacious Studio w/ Full Kitchen

BaileyRating, 5 stars3 weeks ago
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
Top guest favourite
Flat in Bayou Oaks
4.97 out of 5 average rating, 225 reviews

Modern Private Apartment 1 Block from Sarasota Bay

HectorRating, 5 stars1 week ago
Outstanding host and place, definitely will book it again. Perfect location, peaceful environment. One block from ocean.

Apartment rentals with outdoor seating

Top guest favourite
Apartment in Siesta Key
5 out of 5 average rating, 112 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

AleksandraRating, 5 stars1 week ago
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 💕
Guest favourite
Apartment in Siesta Key
4.92 out of 5 average rating, 124 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

PeytonRating, 5 stars1 week ago
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!
Superhost
Apartment in Lido Key
4.8 out of 5 average rating, 104 reviews

LIDO KEY 1 BR/1Bath Heated Pool 16

ChrisRating, 5 stars9 months ago
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
Guest favourite
Apartment in Sarasota
4.86 out of 5 average rating, 148 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

AnnRating, 5 stars1 week ago
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!
Top guest favourite
Apartment in Bradenton Beach
4.99 out of 5 average rating, 133 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

Robert Rating, 5 stars5 days ago
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.
Top guest favourite
Apartment in Longboat Key
4.98 out of 5 average rating, 182 reviews

Condo with a View 1: Beachfront!

JuaniRating, 5 stars2 days ago
Fell in love with this place as soon as I walked in! So peaceful, so beautiful 😍😍 absolutely loved my stay!
Guest favourite
Apartment in Siesta Key
4.94 out of 5 average rating, 106 reviews

Siesta Key Beach Front Condo

JessicaRating, 5 stars3 weeks ago
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!
Guest favourite
Apartment in Siesta Key
4.93 out of 5 average rating, 111 reviews

NO Stairs, beachfront & short walk to the village!

TamaraRating, 5 stars2 weeks ago
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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