Holiday Rentals Osprey from Rp1.133.455: Find Short-Term Rentals & Holiday Accommodations

Q: What are some of the best holiday rentals that Osprey has to offer?

Siesta Key Island Rentals : This holiday home rental outside of Osprey comes with WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

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Top Holiday Rentals in Osprey

"The best place to stay! Super clean home and friendly service. I would stay here again. "

Rp5.954.359 total

includes taxes & fees

30 Jun - 1 Jul

Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

"Nice spot for an overnight stay!"

Rp3.931.655 total

includes taxes & fees

2 Jul - 3 Jul

Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

"Clean,friendly, close to the beach and major shopping center."

"Fun place to stay for family vacation "

Rp11.935.511 total

includes taxes & fees

1 Jul - 2 Jul

"Very clean, wish I could have stayed longer!"

"Perfect location close to the beach clean and cozy place"

Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

"Great place to stay. "

Rp2.509.315 total

includes taxes & fees

30 Jun - 1 Jul

"We loved staying at Kon Tiki!"

Rp2.549.246 total

includes taxes & fees

2 Jul - 3 Jul

Apartment, 2 Bedrooms, Beach View, Beachfront | View from room

"Best place ever "

2 bedrooms, in-room safe, iron/ironing board, free WiFi

"Nice place to stay in SK! "

Rp6.209.182 total

includes taxes & fees

22 Jul - 23 Jul

Barefoot Bungalow W/Pool | Private kitchen

"Great vacation stay "

Rp5.320.075 total

includes taxes & fees

1 Jul - 2 Jul

"Outstanding stay. Great room and amenities with a great locatio. We will return!! "

Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "

Beach nearby, beach umbrellas, beach towels

"The property was in a quiet area and was very pleasant and comfortable. "

"Absolutely beautiful location has everything you need n makes you feel like home"

Outdoor pool, pool umbrellas, pool loungers

"This resort was clean and convenient, would definitely stay here again"

Condo, Pool View | Private kitchen | Full-sized fridge, microwave, oven, stovetop

"A very comfortable stay in Siesta Key. Our apartment had been fully redeveloped since Hurricane Milton. Excellent job. Pool was really good. Nikes to ride. Kayaks to addle in the lagoon. All in allan exceptional choice. "

Rp6.578.162 total

includes taxes & fees

7 Jul - 8 Jul

"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."

Deluxe Studio, Bay View | View from room

"Love love love this place ! Work turns into a leisure ! Every single time I come by. Beach day and then up to work @7pm. Easy access to the beach and nature ! I would recommend bike rentals … TY "

Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Microwave

"Very nice and updated property with a great panoramic view of the bay and ocean. Easy check in and checkout. Close to everything in Montasota Key/Englewood. "

Rp8.604.470 total

includes taxes & fees

2 Jul - 3 Jul

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Find out more about Osprey

Search for holiday rentals in Osprey on Expedia.co.id! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

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Look no further and take a look at our great range of rental properties in Osprey!

Recent reviews of Osprey properties

5/5 Excellent

"Nice modern minimalist industrial hotel. Had a brief power outage during a storm that was resolved immediately. Nice central location. Would stay again."

A verified traveller stayed at Kompose Boutique Hotel

Posted 7 hours ago

5/5 Excellent

"We had a wonderful stay at Tropical Beach Resorts! This is a nice, family-like resort that truly makes you feel at home from the moment you arrive. The location is great—just a 2-minute walk to the beach, and only 5 minutes walking distance to local restaurants, shops, and cafes. The staff was amazing and helpful, always ready with a smile and great recommendations for the area. One of the small but thoughtful touches we loved was the free coffee, tea, and cookies available all day from 8 AM—a perfect way to start or break up your day. Just a heads-up: if you want to relax on the beach, you’ll need to rent chairs and an umbrella. It’s about $40 per day for 2 chairs and 1 umbrella, so plan accordingly. Highly recommend booking in advance, especially during peak seasons—it’s a popular spot for a reason! And another great option - free parking. I would highly recommend this place to stay!"

A verified traveller from brooklyn stayed at Tropical Beach Resorts

Posted 3 days ago

Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Osprey speak positively about the popular beaches and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best holiday rentals that Osprey has to offer?

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 29 Expedia holiday rentals, you're guaranteed to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Siesta Key Beach and Lido Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.

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Search Holiday Rentals in Osprey

Check prices for these dates

Top Holiday Rentals in Osprey

Charming Florida Beach Home w King Bed Patio

Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Ringling Beach House

Captiva Beach Resort

Tiny House Siesta

Kon Tiki Inn

Sea Club I Beach Resort

SeaSpray Resort

Siesta Key Island Rentals

Venice Beach Villas

The Inn On Siesta Key

Tropical Villas of Venice Beach

Barsala at Champions Walk

Siesta Palms By the Beach

Siesta Heron Suites & Villas

Longboat Bay Club

Casey Key Resort - Gulf Shores

Chadwick Cove Resort & Marina

Find out more about Osprey

Recent reviews of Osprey properties

Kompose Boutique Hotel

Magnolia Pointe, BW Signature Collection

Lido Beach Resort

Siesta Key Beach Resort and Suites

Comfort Suites Sarasota - Siesta Key

Golden Host Resort - Sarasota

Carlisle Inn

Zota Beach Resort

Tropical Beach Resorts

Frequently asked questions