
House vacation rentals in Osprey
Find and book unique houses on Airbnb
Top-rated house rentals in Osprey
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Osprey house rentals
House rentals with a pool

Barbara’s Paradise
I had a wonderful stay at this beautiful home! The house was spotless, stylish, and had everything we needed for a comfortable visit. The pool was definitely a highlight — clean, well-maintained, and perfect for relaxing. The whole place felt peaceful and welcoming. I would absolutely stay here again and highly recommend it to anyone looking for a great getaway.

Luxury Oasis Home 3BR 2Bath with Heated Pool
Fantastic location if showing at Fox Lea. House was exactly as photographed and very comfortable.

Great price for May 3/2 Beach House-Heated
Everything was as described and as shown in pictures. House is very roomy. Master is on opposite side of house as other two bedrooms. Two living room areas. Pool area and patio are a nice place to sit and relax. Nokomis Beach is about 10 minuted away. Close to grocery stores, etc.

Beautifully Remodeled Home with Pool Near Siesta
You will not find a better host. We mentioned that we were celebrating a birthday and Yekaterina went above and beyond what we could have even thought of! She surprised us with all of the finishing touches. She made our stay so special! Her place is amazing! The location, the space, EVERYTHING. She is absolutely incredible and we can't say enough about Yekaterina, her place, and our stay. We have been to a lot of airbnb's and many very nice, but Yekaterina is the absolute best host you will find. You will not be disappointed! This is definitely at the top of our list of "Places to stay and visit again!" Thank you Yekaterina!

2bed/2bath with POOL house, close by SIESTA KEY!!!
The house was exactly as described and was private and clean ! We loved the pool and how quiet and peaceful the neighborhood is . Very much enjoyed our stay as first time guests .

Lake Front House with a Pool
This house was spotless, organized and had a loaded kitchen! It is in a amazing location near the beaches and the house came loaded with beach equipment. I would love to come back. Birute was very helpful with us and responsive in timely manner Thansk for all!

Mid-Century Oasis with Pool in Arlington Park 1
This place is perfect. Everything you want in an air bnb and it’s exactly like it looks. My family and I were beyond happy with it. The pool is gorgeous. The location is amazing it’s legit 8 to 10 minutes away from pretty much anything you need or want to do. The house is quiet and the beds are super comfy. I would rent this place every year for a trip. Also the host is awesome! They were there for anything we needed or had questions about and are super nice and friendly people. Thanks again for everything!

Vacation Rental with private swimming pool
While staying at Jan's we were close to the beach and restaurants. The home was very clean, and comfortable. The kitchen was well equipped for what I needed to prepare meals. The bed was super comfy, but a bit high for my 4'11" stature :) If we ever have the chance to get back to Venice, we will definitely book with Jan again.
Weekly house rentals

2 BR House 1.6 miles from Siesta Key Beach
This home was amazing and loved it, host was very nice and responded quickly every time.

Second home vacation rental
Leroy’s place was perfect for our needs for our trip. The location was great for us to get to areas north and south of Venice. The price was a great value compared to other listings that were very similar. Definitely consider this place 😊

Luxury Pet friendly home, 2.7miles to Siesta Key!
We had a wonderful stay at this property. We were in town for our son's sporting event for several days. It was exactly as described and more. It was clean and comfortable and there were so many "extras" that we do not usually experience in other rental properties. The kitchen was fully stocked with utensils, cooking supples, spices, coffee, and more (better than any rental we've stayed in). There is not one negative thing I can say about this place or the host. Honorata was extremely responsive and helpful and allowed us to check in early, which we greatly appreciated as we needed to drop our luggage and go to an event. The location was great, a short drive to the beach, stores, etc. and the neighborhood was quiet and felt safe. We would highly recommend this property and hope to stay there again next time we are in the area. Thank you Honorata and Conrad for a lovely stay!

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

Updated house close to the Beach
I booked this place for my family visiting the area. Place was very clean and stocked with essentials. Huge plus having a washer and dryer to utilize! This home is very cozy and nicely decorated. Yuri's communication was excellent as well! Shoutout to the neighbor as well that took the trash bin and recycle bin to the curb too! This home is in a great location for a beach stay as it is not far from the Nokomis public beach. Highly recommend for the price!!!

Siesta Key Fully-Renovated Unit 5 min to the beach
We had a great stay at Muriel’s place. She was incredibly responsive and welcoming from the start. Her recommendations for beaches and food were spot on and really helped us make the most of our trip. The space was spotless, private, and had everything we needed. It felt like a home away from home. I’d happily recommend this Airbnb to anyone. Muriel is a fantastic host.

Cottage w/Fire Pit Near Siesta!
This house was beyond what we expected and we look forward to renting it again for our next Siesta Key trip. Betsy was outstanding and such a wonderful host.

Palmetto Cottage Retreat
the most perfect cozy cottage for a little florida retreat. great fit for our group of 5! the house had any beach, kitchen, laundry gadget ect, that you could need for a vacation. location was great for us, just a 5-10 minute drive to any surrounding beach, our favorite (and the closest) was manasota, we found over 600 teeth in only 1 hour!!! also lots of thrifts, coffee spots & shops within a shirt drive. the hot tub was super great during storms & for our nightly watch of the new season of love island lol, though it could have been just a tad more up to par cleanliness wise. the neighborhood was cute & felt totally safe and we enjoyed the front porch often! lots of sweet details around the home that really encapsulate the exact vibe we were hoping for! would for sure come & stay at kristins again! thank you for a great stay!!!
Private house rentals

Good Beach Bungalow
My family of 4 recently had a wonderful stay. The house was beautifully appointed, perfectly clean, and well stocked. It is located very close to a great bike trail and we used the bikes that were provided by the hosts. The house also had beach chairs, toys, and a shark tooth sifter for guests to use. The beds were our favorite part and everyone slept wonderfully!

Perfect Getaway Home - 12/min from siesta w/HotTub
We had a fabulous time! We felt right at home. The house was pristine with new appliances, comfortable beds, and a modern aesthetic. Definitely the best house in the neighborhood. We enjoyed the hot tub every night and took advantage of the beaches nearby. Thank you Eddie and Vanessa for sharing this place!

Slice of Paradise in Nokomis
A Slice of Paradise was amazing. Robert was a GREAT Host , he answered every question with in hours, if not minutes. Great location and close to everything. After a couple days it felt like home, when our 6 weeks were up we did not want to leave. We hit 7 different beaches and some 3 or 4 time each. Shark’s and Pop’s were our favorite restaurants long with Dunkin most every day and DQ once a week Detwiler’s Farm Market on Tamiami Trail was our go to for fresh fruits and vegetables. Their bakery was wonderful. We would highly recommended A Slice of Paradise. We can’t wait to go back . Frank, Sue and Paisley.

Morning Side
Great place and close to the beach!

Cozy Coastal - 2bd/2bath with Heated Pool and Spa!
Great location! So close to many different beaches and restaurants. The private pool area was our absolute favorite!

The Pineapple Escape
Our family had a wonderful stay at Claudia's home! She is a very friendly and responsive host. The neighborhood is quiet and in a central location to many wonderful beaches and restaurants. The house and pool were very clean and stocked with many kitchen, bathroom and pool essentials. We definitely recommend the Pineapple Escape!!

Casa Azul a beach oasis! (Pet friendly Duplex)
Our stay at Casa Azul was fantastic. The home was cute & clean and had everything we needed- plenty of clean towels, basic toiletries & laundry soap, and beach gear! And it's an easy walk to Pop's and the beach! Roger & Claudette were great hosts. I definitely recommend Casa Azul

Casa Playa Sleeps 6
The house was perfect for our small family of three and two dogs! The fenced in yard was wonderful and the location was perfect. The neighborhood is quiet with very low traffic. Only a short drive to Siesta Key, downtown, and other attractions.
Quick stats about house rentals in Osprey
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
650 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Seminole Vacation rentals
- Tampa Vacation rentals
- Central Florida Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Saint Johns River Vacation rentals
- Fort Lauderdale Vacation rentals
- Gold Coast Vacation rentals
- Miami Vacation rentals
- Family-friendly rentals Osprey
- Fitness-friendly rentals Osprey
- Rentals with a fire pit Osprey
- Rentals with pools Osprey
- Rentals with a washer and dryer Osprey
- Rentals with a patio Osprey
- Rentals with outdoor seating Osprey
- Rentals with a hot tub Osprey
- Pet-friendly rentals Osprey
- House rentals Sarasota County
- House rentals Florida
- House rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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