
House holiday rentals in Osprey
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Top-rated house rentals in Osprey
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Popular amenities for house rentals in Osprey
House rentals with a pool

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

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.

2bed/2bath with POOL house, close by SIESTA KEY!!!
We absolutely loved our stay here! The house is beautiful and has everything we needed for vacation. The pool was perfect for the kids - they preferred staying home at the pool than going the beach. Romulda was also so helpful and responsive to all our questions. We only wished we had more time to stay here! We’re looking forward to booking again in the future!

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!

Vacation Rental with private swimming pool
Absolutely loved staying here! The home was immaculately clean and stocked beyond my expectations. The pool area was private and the perfect size for two people. The neighborhood felt safe and is super close to food, shopping, etc. One of the best airbnbs I have stayed in. I would go out of my way to stay here again!

The Pineapple Escape
This house was beautiful and very central to many beaches and local restaurants. My wife and I enjoyed our stay and found the location quite and easy to access. The beach amenities like the chairs, umbrella, and wagon were a huge bonus. The kitchen was well stocked with equipment which made it easy to cook and relax on the evenings we spent chilling by the pool.

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!

Cozy & Beautiful Pool Villa in Sarasota County, FL
We’ve just returned from a fabulous 18 day holiday staying at Vera’s beautiful house. Our friends stayed there last year & also loved it. The house is fully equipped with modern appliances & everything you would need for a perfect holiday home. All towels, bedding, washing powder, dishwasher tablets etc etc are all provided & for the beach there are chairs, umbrella & plenty of toys for children to play with in the sand. The pool gets the sun all day & is totally private - the bird cage kept out all mosquitos, flies etc. There are noodles & other inflatables for the pool, a large BBQ & an outside seating area in the shade. We were given the key code for the front door before arrival & the house was immaculately clean and tidy. Occasionally we had a question for Vera, & she was always very quick to respond & helpful. Supermarkets are a two minute drive away & we were never too far away from the beautiful beaches. We definitely hope to return & highly recommend Vera’s house.
Weekly house rentals

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
My wife and I had a great time at this stay. Lots to do at the house along with great beaches and restaurants within a 15-20 minute drive. The house was clean and had everything that you might need. We were able to drive to Disney in just over an hour and a half which provided a different experience to go along with the daily beach/pool trips. Cool AC inside to combat the humid 88 degree weather in June 2025.

The Velvet Blue house 3/2+Pool+5 min Siesta Key
The house looks exactly like the pictures! It was amazing . The house was so beautiful and so clean! Edina , Doris and joe the maintenance guy were very responsive and helpful. The house is on a quiet road . The pool was beautiful especially at night . The house is very close to siesta key beach and there’s so much more all near the home . I would Recommend this house and I will definitely be coming back :) it was a good experience.

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.

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.

Siesta Key Fully-Renovated Unit 5 min to the beach
Amazing host! Super communicative and friendly. I would definitely book again in the future!!

Siesta Key Modern Retreat with Heated Pool & Spa
The house was tucked into a quiet residential community. The home was clean, fresh and spacious. The guest house area with its own bathroom is perfect for a two family stay! The neighborhood was safe to walk in- I walked daily. The neighborhood was really within 15 minutes drive of anything we wanted to do. We spent most of our time at Siesta Key! Leave EARLY for the beach, if that's your day's plan! We would definitely stay again!

Beachside Bliss: Family House-Siesta Beach-3BR/2BA
Very nice place to stay! It is a wonderful location and easy to get to various different beaches! The house was nice and the neighborhood was quiet.

The Avocado Palm Cottage
The place was amazing. It was very clean while taking care of a very nice quiet neighborhood. Tara was definitely on point when I texted. She replied immediately. I would definitely rent here again.
Private house rentals

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!

Cottage w/lanai and garage, 4 mi. Siesta Key
Bedrooms run hot, not much air flow in n there from the AC so we had to leave the doors open to cool the room down a bit over night. Aside from that, beautiful place, very clean, has EVERYTHING you need fully stocked kitchen and fully stocked bathrooms LOVED the place.

3-bedroom home with pool
Marilyn was very responsive when I needed her, and the place looked exactly like the pictures posted. It’s only 8 minutes driving to Nokomis Beach and same for Downtown Historic Venice where you can find all the good local places to eat and buy gifts, as well as Venice Beach at the end of downtown . Publix is very close if you need to buy groceries. Everything was provided at the house, even things for the beach. The house was beautiful and the location was great and quiet. The pool didn’t disappoint. My grandkid loved it . We all did. I recommend 100% this place! Spacious, clean, beautiful and convenient. If it’s available in the future I will stay here again.

Nirvana In Nokomis
Had a great stay during our week in Nokomis. The layout was great and actually had way more space than we even thought. Very easily fit our family of 5. Great set up as well with the master on one side of the house and then the other 2 bedrooms on the other. Neighborhood was very well maintained. You’re about a 3 minute drive or 20 min walk to the beach, but you should already know that when booking. This was one of the best stocked AirBnB’s we’ve stayed at. We truly felt like we were in a home we could live in as there was good flow. Backyard was great as we used the fire pit and hosted some family one evening. Lynda was great to communicate with. She even went above and beyond as we left a camera accidentally. I wouldn’t hesitate to book this place!

Morning Side
Morningside was in a great location, very clean and well furnished. John was very responsive. Beautiful pond in the back with lots of wildlife to see. Very relaxing. The weather was our only issue. It was a risk taken at the start of hurricane season. Therefore we spent quite a bit of time at the house. It was a wonderful stay. Highly recommend.

Private View Villa/Heated Pool/Pickleball/7883
Spacious home with all the amenities you need, well equipped kitchen. We loved the lanai and had all our meals outside. Green and silent surrounding, nice neighbors. A lot of beautiful beaches within 45min (AMI) or just 15min (Siesta). Good shopping possibilities. We had a great time and will be back!

Charming Home in Sarasota-8min from Siesta Key
The hosts were very responsive and very helpful. Their home was spotless. The pool with the enclosure allowed you all the sunshine you could ask for without the bugs! The interior is very spacious and great for hosting dinner. With the turf back yard it’s the perfect hangout for adults and children! The hosts are very thoughtful with items available for the perfect beach day (beach wagon, chairs, a cooler, and lots of fun items for children! We will definitely be visiting again!

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.
Quick stats about house rentals in Osprey
Total rentals
40 properties
Nightly prices starting at
₹4,282 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
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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