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House vacation rentals in Osprey

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Popular amenities for Osprey house rentals

House rentals with a pool

Guest favorite
A clear swimming pool reflects the evening sky, surrounded by a spacious patio. Outdoor seating for dining is arranged under an umbrella, with chairs positioned nearby. Lush greenery provides privacy, and large glass doors lead to the inviting interior of the home.
Home in Sarasota
5 out of 5 average rating, 6 reviews

Pool, Spa, & Private Gym in the Heart of Sarasota

NatalyaRating, 5 stars1 week ago
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.
Guest favorite
A heated saltwater pool is surrounded by a screened enclosure, featuring lounge chairs arranged for relaxation. Tropical plants provide a backdrop, and the pool's clear water reflects the sunlight. A spacious deck area is visible, designed for comfort and leisure activities.
Home in Nokomis
4.91 out of 5 average rating, 54 reviews

"Jellyfish" at The Shore Beach Houses Resort

BenRating, 5 stars4 weeks ago
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.
Top guest favorite
An inviting fire pit is surrounded by several chairs, situated on a lush green lawn. Palm trees sway gently in the background, and in the distance, a saltwater infinity pool glistens under a bright sky with fluffy clouds.
Home in Nokomis
5 out of 5 average rating, 12 reviews

Slice of Paradise in Nokomis

FrankRating, 5 stars2 months ago
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.
Guest favorite
An open-plan living area is depicted, featuring a light-colored sofa and a dining table with chairs. Natural light fills the space through expansive sliding doors, which lead to a covered outdoor area with additional seating and a television. The neutral color palette enhances the spacious feel.
Home in Nokomis
4.95 out of 5 average rating, 19 reviews

Great price for May 3/2 Beach House-Heated

TanyaRating, 5 stars1 month ago
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.
Top guest favorite
A screened lanai features a spacious saltwater pool, surrounded by smooth stone flooring. Sunlight filters through the mesh, illuminating the tranquil water. Lush greenery is visible beyond the enclosure, providing a private and serene outdoor space.
Home in Nokomis
4.99 out of 5 average rating, 94 reviews

Peaceful Getaway just minutes from the beach

RebeccaRating, 5 stars3 weeks ago
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!
Guest favorite
An expansive outdoor area features a large pool with a jacuzzi, surrounded by a spacious pool deck. Modern lounge chairs and seating areas are arranged under a screened enclosure, with a flag gently waving in the background. Warm lighting and a tranquil atmosphere invite relaxation.
Home in Nokomis
5 out of 5 average rating, 11 reviews

Coastal 3BR Getaway|5 Min to Beach|Pool+Peloton

MonicaRating, 5 stars6 days ago
This place was great. It had everything a family could need. It was peaceful and quiet and so much space! We loved it.
Top guest favorite
A screened-in pool area is presented, featuring a heart-shaped heated swimming pool surrounded by a spacious deck. Lush greenery and palm trees are visible beyond the enclosure, providing a serene outdoor setting for relaxation.
Home in Venice
4.91 out of 5 average rating, 190 reviews

Vacation Rental with private swimming pool

PatriciaRating, 5 stars1 week ago
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.
Superhost
A single-story house is presented with a well-maintained lawn featuring green grass and shrubbery. A driveway leads to the garage, while trees provide shade on the property. The inviting front porch opens to a home characterized by modern design.
Home in Sarasota
4.87 out of 5 average rating, 52 reviews

Cozy Coastal - 2bd/2bath with Heated Pool and Spa!

StarlaRating, 5 stars3 weeks ago
Great location! So close to many different beaches and restaurants. The private pool area was our absolute favorite!

Weekly house rentals

Top guest favorite
A private pool and hot tub are enclosed within a screened area, featuring a calm water surface that reflects sunlight. The surrounding deck is finished with sleek tiles, offering a spacious area for relaxation. Lush greenery is visible just beyond the enclosure.
Home in Nokomis
5 out of 5 average rating, 37 reviews

Barbara’s Paradise

ArianRating, 5 stars1 month ago
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.
Guest favorite
An open living area is presented, featuring a blue couch and a wooden coffee table. A dining table with four chairs sits nearby, complemented by a kitchen with white cabinetry and modern appliances. A Christmas tree adds a seasonal touch, while windows allow natural light.
Home in Sarasota
4.94 out of 5 average rating, 71 reviews

2 BR House 1.6 miles from Siesta Key Beach

MaryRating, 5 stars3 weeks ago
This home was amazing and loved it, host was very nice and responded quickly every time.
Guest favorite
The entrance of a modern single-story home is showcased, framed by lush green grass and mature trees. A paved driveway leads to a two-car garage. Soft lighting highlights the front entry, while large windows invite natural light into the living area.
Home in Nokomis
4.87 out of 5 average rating, 54 reviews

Luxury Oasis Home 3BR 2Bath with Heated Pool

JaclynRating, 5 stars1 month ago
Fantastic location if showing at Fox Lea. House was exactly as photographed and very comfortable.
Top guest favorite
The single-story home features a light-colored exterior with a sloping roof. A covered entrance welcomes guests, while a driveway accommodates parking next to the house. Multiple windows allow natural light to fill the front rooms, and lush green grass surrounds the entrance.
Home in Englewood
5 out of 5 average rating, 26 reviews

6 Miles to Beaches | Cozy Home w/ Screened Lanai

LindsaiRating, 5 stars2 days ago
Christopher was amazing and communicated very well. He was a great host!
Top guest favorite
A single-story home is set amidst lush greenery, featuring a manicured lawn and tropical landscaping. The front entrance is framed by palm trees, and a driveway leads to a single-car garage. The house displays a welcoming façade with well-maintained finishes.
Home in Venice
5 out of 5 average rating, 15 reviews

Morning Side

CharlieRating, 5 stars1 week ago
Great place and close to the beach!
Top guest favorite
A cozy living area is captured, featuring a plush brown sofa adorned with soft pillows and a beige throw blanket. A round wooden coffee table complements the seating, while minimalistic artwork is displayed on the wall above. A potted plant adds a touch of greenery to the space.
Home in Sarasota
5 out of 5 average rating, 67 reviews

Siesta Key Fully-Renovated Unit 5 min to the beach

AlecRating, 5 stars4 days ago
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.
Top guest favorite
A handcrafted wooden pelican figurine stands prominently on the countertop, adding a coastal touch. Above, pendant lights hang beneath a bamboo ceiling, providing a warm glow. The background reveals glimpses of a colorfully decorated space with various shelves and artwork.
Home in Sarasota
4.97 out of 5 average rating, 73 reviews

Sandy Feet Retreat- Cozy Bungalow & Outdoor living

ShelbyRating, 5 starstoday
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.
Top guest favorite
An inviting fire pit is surrounded by a circular stone seating area, featuring two Adirondack chairs. Decorative cushions add color to the seating. A spacious, fenced backyard is complemented by a serene evening sky with pastel hues.
Home in Sarasota
4.99 out of 5 average rating, 80 reviews

Cottage w/Fire Pit Near Siesta!

AmberRating, 5 stars2 weeks ago
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

Top guest favorite
A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.
Home in Sarasota
5 out of 5 average rating, 60 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

KristinRating, 5 stars6 days ago
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.
Guest favorite
A bright living area features a spacious white sofa facing a modern entertainment unit. Two dark blue armchairs are positioned nearby. A large window allows natural light to fill the room, while light wood flooring and a neutral area rug enhance the open space.
Home in Nokomis
5 out of 5 average rating, 5 reviews

Good Beach Bungalow

KateRating, 5 stars2 months ago
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!
Guest favorite
A spacious living room is presented with neutral-toned sofas adorned with colorful cushions. A coffee table with decorative items is centered between the seating, while light enters through large windows framed by soft blue curtains. A decorative plant adds a touch of greenery.
Home in Sarasota
5 out of 5 average rating, 25 reviews

Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!

DarrellRating, 5 stars2 weeks ago
Great stay, great villa and wonderful amenities! Very safe and quiet!
Guest favorite
A modern living area features a light-colored sofa accompanied by a wooden coffee table. The room is enhanced by a large wall art piece depicting a beach scene. An open layout is evident, with a view of a kitchen area and bar seating in the background.
Home in Sarasota
4.9 out of 5 average rating, 96 reviews

2Bed/1Bath Entire House Mins to Beach+Downtown

ElizabethRating, 5 stars2 weeks ago
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!
Top guest favorite
A spacious bedroom is illuminated by natural light from sliding glass doors. The area features a large bed with blue accents, a comfortable armchair, and a desk. A muted rug complements the wooden flooring, while plants and decor add a touch of greenery.
Home in Sarasota
4.97 out of 5 average rating, 31 reviews

Resort-Style Vacation Villa

OxanaRating, 5 stars6 days ago
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!
Top guest favorite
A screened lanai showcases a heated pool and spa, surrounded by twinkling string lights. Lounger chairs and outdoor dining furniture are positioned nearby. A grassy area is visible beyond the pool, while a pink inflatable floats in the water, enhancing the serene outdoor setting.
Home in Sarasota
4.98 out of 5 average rating, 51 reviews

Charming Home in Sarasota-8min from Siesta Key

KhloeyRating, 5 stars2 weeks ago
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!
Top guest favorite
A charming house is set within a spacious yard, featuring lush green grass and palm trees. A driveway leads to a light-colored exterior, with the front entrance framed by tropical plants. A clear blue sky adds to the inviting atmosphere of the property.
Home in Nokomis
4.98 out of 5 average rating, 47 reviews

The Pineapple Escape

ErinRating, 5 stars1 week ago
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!!
Guest favorite
The outdoor space is enclosed by a screened lanai, showcasing a heated saltwater pool and a dining area with a large table that seats eight. Lounge chairs and a BBQ grill are positioned near the pool, surrounded by tropical landscaping and a clear blue sky.
Home in Sarasota
4.96 out of 5 average rating, 85 reviews

3 bedroom Heated salt water pool close to Siesta

KristoferRating, 5 starstoday
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

Destinations to explore

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  4. Sarasota County
  5. Osprey
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