Holiday rentals in Osprey

5 out of 5 average rating, 191 reviews

Flat in Sarasota

Modern Luxury Apartment in a House Near Siesta

Large modern construction 950 square foot 1 bedroom apartment. Beautifully furnished, efficient apartment attached to the side of the main house. This unit has a private entrance with bright, modern interior and high ceilings. The apartment offers 1 King bed. The full bathroom has a large shower. A Washer and dryer located inside the apartment. Nestled on a quiet street with easy access to Siesta key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key. Great location!

4.98 out of 5 average rating, 42 reviews

Home in Osprey

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

Superhost

4.72 out of 5 average rating, 335 reviews

The Ibis Cottage

Freshly renovated, The Ibis Cottage is a cozy studio on a beautiful property overlooking a small lake. It is a 5 minute drive to Nokomis Beach, Siesta Beach and Venice Beach are within easy reach, and a block away to the Legacy Trail bike path (Sarasota to Venice). Enjoy seeing a variety of birds on the property including the ibis, heron, and snowy egret. The cottage is conveniently located between Sarasota and Venice. The perfect location for enjoying the Gulf coast and outstanding beaches.

4.98 out of 5 average rating, 106 reviews

Apartment in Sarasota

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

4.97 out of 5 average rating, 276 reviews

Guest house in Sarasota

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.

4.89 out of 5 average rating, 221 reviews

Tiny home in Sarasota

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

4.92 out of 5 average rating, 180 reviews

Guest house in Sarasota

Cozy Guesthouse in central Sarasota!

This cozy independent guesthouse is perfect for all ocations from a few business day stay to a vacacion getaway. Near to siesta key beach! Enjoy a private room with a comfortable bed, a bathroom with a great shower and hot water, plus a cozy bar-style area perfect for preparing snacks and coffee. You’ll also have access to a small patio where you can unwind, and we provide beach essentials. Perfect for travelers seeking comfort and peace, and a well-equipped space. We’d love to host you!

4.97 out of 5 average rating, 58 reviews

Cottage in Osprey

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. Hurricane Milton: Yes, we are cleaned up and have power and internet!

4.92 out of 5 average rating, 213 reviews

Guest suite in Sarasota

MG Tropical Stay. With private entrance and patio.

Welcome to our one year old Guest Room.(Adults only). The attached Modern open concept studio style room is all yours with your own: kitchennete, bedroom, bathroom, and secluded patio! no shared spaces at all. With private entrance and two cars parking space. Quiet location -Spotless upon arrival We are welcoming you to our place! Location is 3.8 miles from downtown 7.9 miles from Lido Key Beach and less than 5 miles from Main Mall, UTC Shopping, and Restaurants areas.

4.96 out of 5 average rating, 110 reviews

Cute Little Getaway

Close to the beach and walking distance to 5 restaurants, including one on the water. Our place is less than 2 miles from Nokomis Beach! We have you covered on beach equipment, wagon, chairs, towels and umbrella. The backyard boasts a relaxing, beautiful escape with resort style touches. We have a gas grill to cook your catch, a high powered outdoor fan, and comfy seating in the shade. The house is freshly modernized, open and airy. You will enjoy an outfitted kitchen.

4.93 out of 5 average rating, 184 reviews

Home in Sarasota

Sea-esta Cottage- Cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand-new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

4.97 out of 5 average rating, 153 reviews

Cottage in Nokomis

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!

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Other great holiday rentals in Osprey

4.84 out of 5 average rating, 83 reviews

Holiday home in Nokomis

"Sea Turtle" Saltwater Pool, Shore Beach House

JosiahRating, 5 stars1 week ago

Such a wonderful location and stay. My wife and I have been traveling down the west coast to explore numerous beach towns. This location was our favorite so far! Amazing fishing, swimming, dolphin viewing, and manatee viewing by the jetty. We would love to come back!

4.93 out of 5 average rating, 88 reviews

Guest house in Sarasota

Cabana/Guest house w/spa/pool 5min to Siesta key.

СергейRating, 5 stars1 month ago

We are very glad that we managed to choose this house. Large, spacious, with all the amenities and close to all the beautiful beaches. John is a big and kind person with an open heart and a bright soul. He does everything to make his guests feel comfortable. Thank you John.

4.91 out of 5 average rating, 58 reviews

Home in Sarasota

Oceanfront Home with Heated Pool in Fishers Haven

DinaRating, 5 stars2 months ago

House is immaculate! Super clean and comfortable. Beds and linens were luxurious! Ceiling fans in entry room including the screened in porch. Nice touch! Backyard waterfront is amazing. We used pool and hot tub multiple times per day. We fished off the dock and caught a few catfish. Sergiy was a perfect host. Excellent communication and direction when needed. Highly recommend!

4.96 out of 5 average rating, 79 reviews

Apartment in Sarasota

Blue studio perfect for 2, just 5 min from beach

AmandaRating, 5 stars5 days ago

This was the perfect place for two people. Had everything we needed for a weekend away. The hosts were so nice and it was an easy place to come and go from. Will be back again!

4.98 out of 5 average rating, 46 reviews

Home in Osprey

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!

4.96 out of 5 average rating, 98 reviews

Home in Sarasota

Sea La Vie On Brink- cheerful 3/2 w/ shuffleboard

SherryRating, 5 stars2 months ago

We enjoyed staying here and will be back.

5 out of 5 average rating, 24 reviews

Lake View, 6 Miles From Beach

AudreeRating, 5 stars5 days ago

This place is amazing!!! Jay (the host) was super responsive and helpful. The house is gorgeous with all of the amenities you could want including kayaks, fishing poles (there's a lake in your backyard), towels, beach chairs, coolers, etc. The house is in a gated community with a beautiful zero entry infinity pool (heated) that my boys really enjoyed. There's 3 bedrooms with plenty of space for a large family. I really can't say enough about this house. We will be back next year!