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

Pool, Spa, & Private Gym in the Heart of Sarasota
We had a great stay at the house. Loved the interior decor. Looks like the home was remodeled recently. Everything was fresh and clean. We loved hanging out by the pool. Backyard was very private and peaceful. Posts were very quick with their responses if I had any questions about the home. We would definitely stay at the Home again when we’re in town.

"Jellyfish" at The Shore Beach Houses Resort
Rich and Marianne's place was excellent! The resort has approximately 6 units, a shared pool, ample parking and is located in a great spot, 10 minutes walk to restaurants, 12-15 to the beach. My wife and I had a blast, and Rich and Marianne were helpful, responsive and a pleasure to communicate with.

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.

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.

Peaceful Getaway just minutes from the beach
Christa's home is very nice. The home was clean and had everything we needed. The pool area was our favorite. Even though we didn't need it due to the ages of the kids, we appreciated the removable fence around the pool. The beach was about 5 minutes away, along with two water front restaurants. Christa had everything we needed for the beach along with pool toys. There was a ping pong table in the garage along with 3 bikes. The neighborhood was quiet. Christa was very responsive with my questions. We will definitely stay again. Thanks Christa!

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.

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.

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!
Weekly house rentals

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.

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.

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

6 Miles to Beaches | Cozy Home w/ Screened Lanai
Christopher was amazing and communicated very well. He was a great host!

Morning Side
Great place and close to the beach!

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.

Sandy Feet Retreat- Cozy Bungalow & Outdoor living
We had a great stay at Tyler’s place! It was a beautiful home and our dogs loved the backyard. The central location is Sarasota was perfect! We hope to stay here again in the future.

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.
Private house rentals

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
Erinn was an amazing host - she would respond immediately to any text and was always friendly and helpful. The house is as good as it looks if not better! My husband complains about every airbnb I book but he even he had to admit this one was top notch.

Buena 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!

Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!
Great stay, great villa and wonderful amenities! Very safe and quiet!

2Bed/1Bath Entire House Mins to Beach+Downtown
This house was adorable! Loved the decor - cute touches and uncluttered throughout. Drawers/cabinets were clearly labeled and there were all sorts of things there that you might have forgotten- even hair ties! Bed was comfortable. Whole place was cozy and comfy- I didn’t want to leave! Tons of great recommendations in the guest book by the front door. I wholeheartedly recommend this home!

Resort-Style Vacation Villa
This is our second time at this place. Shirley’s place is simply the best. From spacious home, to fully stacked kitchen, to fabulous floating chairs and beach wagon, to top washing and dryer machines. I literally feel at home while being on vacation. I am so grateful to Shirley for setting up her place and letting us enjoy it. We will be back again!

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!

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!!

3 bedroom Heated salt water pool close to Siesta
Very beautiful home! Great place to stay and enjoy as well as just close enough to Siesta Keys beach! Peaceful and very clean!! Definitely a must stay!!
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
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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