Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (217)
"Good location clean easy check in"
Tropical Villas of Venice Beach

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

9.2 out of 10, Wonderful, (35)
"This was a great home to stay in! My friend and I were in town for a birthday. The neighborhood is very safe and close to so many local spots. The owners were very responsive and helpful. "
The price is AU$574
includes taxes & fees
27 Nov - 28 Nov
Gorgeous Pool house 5 min from the beach, shopping and restaurants I

Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

10.0 out of 10, Exceptional, (17)
"It was wonderful. Wish we could have stayed longer"
The price is AU$691
includes taxes & fees
25 Nov - 26 Nov
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Villa Azul: IMG, Pool, Lake Front, Close to Beaches/New Listing Discount!

10.0 out of 10, Exceptional, (5)
"We had a wonderful vacation at this beautiful property. The view and sunset from the pool is gorgeous. The house is very spacious and nicely decorated. The kitchen has been stocked with everything you will ever need. Communication was outstanding."
Villa Azul: IMG, Pool, Lake Front, Close to Beaches/New Listing Discount!

NO STORM DAMAGE! 5 STAR SIESTA KEY BEACH, 80 STEPS to BEACH, RESORT POOL, 6 BED

10.0 out of 10, Exceptional, (124)
"The property is excellent. Location is ideal for beach. It is an easy 10 min walk to the village and 100 feet from beach access stop. You don’t have to worry about parking at all. The house is loaded with everything you need for going to the beach. Owner David is outstanding. Very easy to reach and prompt responding to texts . Exceptional stay. Highly recommended "
NO STORM DAMAGE! 5 STAR SIESTA KEY BEACH, 80 STEPS to BEACH, RESORT POOL, 6 BED

Private Home near Lido/Siesta Key Beach & Downtown

10.0 out of 10, Exceptional, (38)
"Great stay at this cozy and clean house. Definelitely recommend!!"
The price is AU$628
includes taxes & fees
10 Dec - 11 Dec
Private Home near Lido/Siesta Key Beach & Downtown

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.8 out of 10, Exceptional, (77)
"We stayed for 5 nights and wished we could have stayed longer! The home was perfect for our needs with spacious rooms, clean and well taken care of, and all the amenities we could use. The pool and canal view were added bonuses. The location was especially great for us. We walked daily to the Village to enjoy the variety of restaurants and also the gorgeous public beach. The host was so responsive to questions and also helped us with a forgotten item. Above and beyond! Recommend so...
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach

9.8 out of 10, Exceptional, (33)
"We really enjoyed our stay!.. Awesome tiny house,was just as described..We will certainly be back for future getaways!"
The price is AU$315
includes taxes & fees
1 Dec - 2 Dec
Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach

Clean Perfectly Remodeled Townhome, Steps From the Private Beach. 3 night min

9.8 out of 10, Exceptional, (194)
"It was clean and beautiful. We had a great time!!!"
Clean Perfectly Remodeled Townhome, Steps From the Private Beach. 3 night min

NEW !! Sarasota House w HEATED Pool 3-4 bed/3 bath

9.0 out of 10, Wonderful, (92)
"We enjoyed our stay at Buckeye house in Sarasota Fl. The house was clean and had everything we needed. The pool was nice and had toys and safety devices for our little ones. Very pleased"
NEW !! Sarasota House w HEATED Pool 3-4 bed/3 bath

Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

9.4 out of 10, Exceptional, (32)
"We liked this place a lot!! Definitely will come back!!"
Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

HEATED pool, bike to Siesta, quiet street, 1 MILE to beach INTACT after storm

10.0 out of 10, Exceptional, (91)
"We had booked another rental in Siesta Key but after the hurricane came thru the rental was cancelled. Luckily we were able to book this house and it was very nice! In the pool everyday! Thank you.. Very comfortable place!"
HEATED pool, bike to Siesta, quiet street, 1 MILE to beach INTACT after storm

Venice beaches, shopping, dining, biking close by. Wonderful, warm, newer pool.

10.0 out of 10, Exceptional, (74)
"The place is well located to all areas of Venice. The home is much homier and accommodating than expected. Pool area is great and relaxing especially after a long day out or from beach. Patrick responds very quickly when needed. "
Venice beaches, shopping, dining, biking close by. Wonderful, warm, newer pool.

Sunny Sarasota Abode w/ Yard ~ 1 Mi to Dtwn!

9.8 out of 10, Exceptional, (20)
"We came from Oklahoma for my husband to have a natural hernia tissue repair and we were more than pleased with the location on the property. It was so beautiful and so convenient that we were able to use their garage as it made it so much easier getting my husband in and out and my 1.5 year old. We were close to the ocean, hospital, and the surgery center. The amount of space was so nice, the cleanliness was outstanding, the yard was so charming and peaceful. We definitely want to come back to...
Sunny Sarasota Abode w/ Yard ~ 1 Mi to Dtwn!

Blue Pineapple Delight

10.0 out of 10, Exceptional, (11)
"I am working nearby this summer and needed a safe, pet-friendly and spacious cottage to stay. This checked all the boxes and the owner was very gracious with checking in/out dates. I even picked a fresh pineapple out of the front yard to eat! It’s an “old Florida” vibe in the neighborhood, super close to beach area and next to a Boy Scout lodge. As a female traveling with my daughter I felt safe. The washer/dryer was appreciated! We enjoyed the screened porch in the evenings. The cottage is very...
Blue Pineapple Delight

New home 3/2 renovation 3 miles to Siesta Key

8.6 out of 10, Excellent, (4)
"The house was very clean with helpful amenities. However, the only complaint we have would be about the water pressure in the showers. Overall, it was a great experience in a great location, very close to the beach!"
The price is AU$523
includes taxes & fees
1 Dec - 2 Dec
New home 3/2 renovation 3 miles to Siesta Key

Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶

10.0 out of 10, Exceptional, (3)
"The house was perfectly set up for the beach with a family. Beach was perfect and 2 minute walk. House was gorgeous"
Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶

Private Home in Siesta Key, Florida Gulf of Mexico, USA

10.0 out of 10, Exceptional, (33)
"Our host, Paul, was incredibly nice and extremely responsive throughout the booking process and our stay. The home was very clean and had everything we needed stocked. There is lots of room in the home to spread out. The home itself is located incredibly close to every major activity in Sarasota. Everyone in our party was very pleased with our stay, and we are looking forward to potentially stay again in the future!"
Private Home in Siesta Key, Florida Gulf of Mexico, USA

Roselawn St | Private Pool, Covered Patio + Fire Pit!

9.8 out of 10, Exceptional, (10)
"This is one of the best stays I have ever had in Sarasota, with or without a tropical storm (Debby) growing into a hurricane off the coast. Two surprises were it is more roomy in some places than the pictures suggest and it had two king and two queen beds, not just one king. Pool was perfect and the fans on the patio were welcome touch for being there in early August. Kids loved playing hoops so much they never got to the other games the house was equipped with. I can't recommend it enough and...
Roselawn St | Private Pool, Covered Patio + Fire Pit!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Osprey

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2074)
"Our suite was very clean and the hospitality was wonderful. Would definitely recommend to anyone. If we ever visit the area again we would definitely stay there."
The price is AU$304
includes taxes & fees
24 Nov - 25 Nov
Hibiscus Suites - Gateway to Siesta Key

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (211)
"This property is off the charts wonderful. Beautiful grounds, kind staff and incredible rooms. Loved every minute of our four night stay!"
The price is AU$722
includes taxes & fees
4 Dec - 5 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
Tropical Beach Resorts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.