Holiday rentals in Osprey

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Top-rated holiday rentals in Osprey

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Guest favourite

Flat in Sarasota

4.88 out of 5 average rating, 135 reviews

Pets friendly modern studio 5 mi to Siesta Key

Renovated Studio/1 full bath apartment in a duplex house with separate entrance. Located in a West of "The Trail" in Southern Central Sarasota. Ideally close to Siesta Key, Turtle, Osprey and Nokomis beaches. Bike Routes throughout and short drive to downtown Sarasota, Osprey, Venice and wonderful amenities of Sarasota Lifestyle. Walking distance to restaurants, Selby aquatic center, Vamo Sarasota Bay Park, Westfield Mall, Total Wine, Costco, Target and CVS. Great, quiet and secure neighborhood.

5–12 Dec

₹9,787 per night

Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 476 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

4–11 Aug

₹9,045 per night

Superhost

Villa in Nokomis

4.91 out of 5 average rating, 141 reviews

MAY SALE! Sarasota Family BEACH Villa 2KING BR/2BA

EXCLUSVE CASEY KEY beach just .5 mi. away!! Sarasota 10 mins away! Miles of uncrowded beach! Two KING bedrooms, two bath villa! The Villa is a short 1 minute drive from Casey Key Beach! Two new 55" 4K T.V's. New appliances and furnishings throughout! Kayaking, biking, boating... all right here! Lush tropical backyard and fire pit. There are many wonderful restaurants and shops within a five minute drive. Restoring this Villa has been a labor of love for us, read our reviews!! Come stay...:)

18–25 Dec

₹14,885 per night

Guest favourite

Guest suite in Sarasota

4.9 out of 5 average rating, 289 reviews

Quaint 1-queen bed/1 bath apartment in Sarasota

A quaint one bedroom country apartment tucked away on 5 acres Sarasota. We are located in a quiet, private neighborhood 8 minutes from restaurants and shops at University Town Center and 20-30 mins from Siesta Key and Lido Beach. Has 1 bedroom, 1 bath apartment has a queen size bed. Living room with a two swival rocking chairs, TV. Equipped with a refrigerator, double burner cook top, coffee pot, toaster, and microwave.The apartment also has a washer and dryer and a carport for parking.

30 Apr – 7 May

₹7,410 per night

Guest favourite

Guest house in Sarasota

4.96 out of 5 average rating, 246 reviews

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

4–11 Sep

₹8,309 per night

Guest favourite

Flat in Nokomis

4.88 out of 5 average rating, 168 reviews

Casa del Sol I (Non-Smoking Property)

A four minute walk and your toes are in the sand on the beach of beautiful Nokomis Beach on the Gulf of Mexico! This quiet, comfy one bedroom apartment with a sunset deck is on the second floor over your private 2 car carport. Newly remodeled with 49” TV with AppleTV you can sleep 2 additional guests on a comfortable queen size air bed which automatically opens up and closes at a touch of a button. Shopping, banking and post office 1 mile away and 10 restaurants a few minutes away.

7–14 May

₹8,422 per night

Guest favourite

Home in Sarasota

4.98 out of 5 average rating, 198 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

11–18 Aug

₹8,608 per night

Guest favourite

Guest suite in Sarasota

4.91 out of 5 average rating, 269 reviews

Siesta Keys stylish and affordable Airbnb.

Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

10–17 Aug

₹7,873 per night

Guest favourite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Bella Vita! (The Good Life!)…that feeling when you wake up each day in this little slice of Paradise. This is the spot to enjoy a warm peaceful getaway from the rest of the world...just arrive with your bathing suit/flip flops and walk 1.5 blocks to the warm Gulf waters. Tranquillity of beach life, beautiful sunsets and lazy days of fishing and bird watching. Visit the Jetties, where you can see dolphins, manatees and rays, is only 1/2 mile away.

16–23 Sep

₹9,973 per night

Guest favourite

Bungalow in Osprey

4.78 out of 5 average rating, 318 reviews

Osprey,Buttonwood Cottage.Hot tub -patio.Sublime !

Floridian Tiny Cottage! Buttonwood Cottage is wonderfully located central to the downtowns and beaches of Sarasota and Venice with a private patio space and hot tub. 15 minutes away for the number 1 beach in USA "Siesta Key" . You'll feel that you stepped back in time upon arrival to our charming homestead. I follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights:

30 Apr – 7 May

₹8,858 per night

Guest favourite

Guest suite in Sarasota

4.97 out of 5 average rating, 349 reviews

Adorable studio close to Siesta beach!

Come stay in this private studio with its own fenced in patio in the back! Has shared washer and dryer. New Queen bed ,pullout couch (twin). gas grill,toaster oven/airfryer, microwave , hot plate for cooking and full fridge plus ac unit. Rainfall showerhead and river stones on shower floor. beach chairs ,towels available. Off street parking in driveway. The famous, huge fresh market " Detweilers" is only 1.5 miles away

30 Aug – 6 Sep

₹7,666 per night

Guest favourite

Cottage in Osprey

4.95 out of 5 average rating, 22 reviews

Mattie’s Cottage by the Bay

Enjoy this 1913 Florida vernacular cottage! Carefully restored, thoughtfully updated house on a quiet, tree-canopied street in historic Osprey, one of Sarasota County’s oldest settlements. Enclosed front porch, screened back porch, and tin roof. Walk to the bayfront, restaurants, shopping, library, parks, and historic sites. A short drive takes you to famous Gulf beaches and all Sarasota and Venice have to offer.

2–9 May

₹8,345 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Osprey holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Osprey's top sights

Walmart Supercenter14 locals recommend

Casey Key Fish House66 locals recommend

Evies @ Spanish Point17 locals recommend

Mad Moe's Sports Pub & Grill12 locals recommend

Max's Table15 locals recommend

Tervis Store4 locals recommend

Other great holiday rentals in Osprey

Guest favourite

Home in Osprey

4.92 out of 5 average rating, 38 reviews

Private house with loft

27 Aug – 3 Sep

₹12,843 per night

Guest favourite

Flat in Nokomis

4.98 out of 5 average rating, 66 reviews

Charming 1 bedroom apartment for 2 with pool.

12–19 Sep

₹10,483 per night

Guest favourite

Home in Osprey

4.91 out of 5 average rating, 32 reviews

Sand Dollar Cottage - 15m to Siesta / Casey Key

29 May – 5 Jun

₹13,352 per night

Guest favourite

Apartment in Nokomis

5.0 out of 5 average rating, 15 reviews

Private Studio (entire space)

14–21 Sep

₹7,695 per night

Guest favourite

Home in Osprey

5.0 out of 5 average rating, 23 reviews

Heated Pool | 3 Beds | Near Beaches and parks

20–27 Sep

₹14,884 per night

Guest favourite

Home in Osprey

4.95 out of 5 average rating, 22 reviews

Charming Florida Cottage - Kayaks Included

31 Oct – 7 Nov

₹24,212 per night

Guest favourite

Home in Nokomis

4.9 out of 5 average rating, 39 reviews

Cheerful, sparkling 2 bedroom cottage, 1.8 miles from beach

3–10 Jul

₹7,989 per night

Guest favourite

Cottage in Nokomis

4.92 out of 5 average rating, 84 reviews

The "Turtle Cottage" - a charming beachy retreat.

11–18 Dec

₹11,026 per night

Show all

Quick stats about holiday rentals in Osprey

Total rentals	80 properties
Rentals with a pool	60 properties have a pool
Pet-friendly rentals	30 properties allow pets
Family-friendly rentals	60 properties are a good fit for families
Total number of reviews	1.6T reviews
Nightly prices starting at	₹5,010 before taxes and fees

Holiday rentals in Osprey

Top-rated holiday rentals in Osprey

Flat in Sarasota

Guest suite in Sarasota

Villa in Nokomis

Guest suite in Sarasota

Guest house in Sarasota

Flat in Nokomis

Home in Sarasota

Guest suite in Sarasota

Cottage in Nokomis

Bungalow in Osprey

Guest suite in Sarasota

Cottage in Osprey

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Osprey holiday rentals

Stay near Osprey's top sights

Other great holiday rentals in Osprey

Home in Osprey

Flat in Nokomis

Home in Osprey

Apartment in Nokomis

Home in Osprey

Home in Osprey

Home in Nokomis

Cottage in Nokomis

Quick stats about holiday rentals in Osprey

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore