Some info has been automatically translated. Show original language

House vacation rentals in Osprey

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Osprey house rentals

House rentals with a pool

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
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.
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.
Guest favorite
A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.
Home in Sarasota
4.96 out of 5 average rating, 142 reviews

Beautifully Remodeled Home with Pool Near Siesta

NancyRating, 5 stars3 weeks ago
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!
Guest favorite
A screened enclosure surrounds the pool area, offering protection while allowing light to filter through. Tropical plants are positioned along the perimeter, complementing the spacious pool deck. Two lounge chairs with teal cushions are placed nearby, providing a relaxing spot for sunbathing.
Home in Sarasota
4.95 out of 5 average rating, 212 reviews

2bed/2bath with POOL house, close by SIESTA KEY!!!

RebeccaRating, 5 stars2 weeks ago
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 .
Guest favorite
A screened-in pool area is showcased, featuring a heated pool with clear blue water. Sunlight casts shadows on the tiled surface, while a picturesque view of a private lake and surrounding greenery is visible in the background.
Home in Sarasota
4.94 out of 5 average rating, 133 reviews

Lake Front House with a Pool

Jose & ZullyRating, 5 stars3 weeks ago
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!
Guest favorite
A sparkling pool is surrounded by a spacious patio, featuring lounge chairs and a vibrant red umbrella. Lush tropical landscaping creates a serene retreat, providing an inviting space for relaxation and leisure under a clear blue sky dotted with fluffy white clouds.
Home in Sarasota
4.96 out of 5 average rating, 119 reviews

Mid-Century Oasis with Pool in Arlington Park 1

MatthewRating, 5 stars1 week ago
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!
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.

Weekly house rentals

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
A modest bedroom features a wooden bed frame with a light-colored bedspread. Two bedside tables are positioned on either side, with elegant lamps providing soft light. Dark curtains frame a window, and a decorative area rug adds texture to the floor.
Home in Venice
4.92 out of 5 average rating, 39 reviews

Second home vacation rental

MichelleRating, 5 stars1 week ago
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 😊
Top guest favorite
A modern kitchen is highlighted by a central island with a dark countertop and multiple drawers. Sleek white cabinets complement stainless steel appliances, while a coffee maker and kettle are positioned on the counter. A potted orchid adds a touch of color to the space.
Home in Sarasota
4.99 out of 5 average rating, 69 reviews

Luxury Pet friendly home, 2.7miles to Siesta Key!

CarenRating, 5 stars5 days ago
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!
Guest favorite
The exterior view of Bayview House showcases a charming two-story structure with a light peach facade and white trim. Lush landscaping with colorful tropical plants surrounds the entrance, which features a covered porch leading to the private screened lanai.
Home in Osprey
4.98 out of 5 average rating, 46 reviews

Bayview House - Osprey - 1 block to Bay!

DilyaraRating, 5 stars1 month ago
Excellent location,big house,everything you need is stay with kids,awesome owner!
Top guest favorite
A one-story house is shown with a carport on the left side. The front yard features low shrubs and tall palm-like plants. Large windows are visible, allowing natural light to enter. The house is set against a background of trees and a clear blue sky.
Home in Nokomis
5 out of 5 average rating, 21 reviews

Updated house close to the Beach

JaneRating, 5 stars1 week ago
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!!!
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 stars3 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
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.
Guest favorite
A charming single-family home features a freshly painted exterior with a light blue front door. Lush greenery, including palm trees and flower beds, enhances the inviting curb appeal. A driveway leads to an attached garage, and a neatly maintained lawn stretches across the property.
Home in Venice
4.93 out of 5 average rating, 57 reviews

Palmetto Cottage Retreat

DanaRating, 5 stars2 weeks ago
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

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!
Superhost
The exterior of the home is highlighted by a manicured lawn and palm trees, framed by a driveway leading to a wooden garage door. A clean, modern design features a light-colored facade under a silver metal roof, set against a clear blue sky.
Home in Sarasota
4.91 out of 5 average rating, 57 reviews

Perfect Getaway Home - 12/min from siesta w/HotTub

VadimRating, 5 stars2 months ago
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!
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, 11 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.
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!
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 stars2 weeks ago
Great location! So close to many different beaches and restaurants. The private pool area was our absolute favorite!
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 stars6 days 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 exterior of the duplex is presented, featuring a charming blue facade and a spacious wooden deck. Brightly colored adirondack chairs are arranged around a fire pit in the foreground, surrounded by grassy areas and lush greenery. A clear sky is visible with the sun shining above.
Home in Nokomis
4.9 out of 5 average rating, 10 reviews

Casa Azul a beach oasis! (Pet friendly Duplex)

AutumnRating, 5 stars3 weeks ago
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
Top guest favorite
A charming blue house is presented with a gabled roof and dormer windows. Lush greenery and colorful flowers surround the entrance, which features a white door and inviting walkway. The bright sky with scattered clouds complements the vibrant exterior and landscaped yard.
Home in Sarasota
5 out of 5 average rating, 14 reviews

Casa Playa Sleeps 6

SarahRating, 5 stars1 week ago
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

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Osprey
  6. House rentals