Osprey Village Holiday Rentals from €126: Search Short-Term Rentals

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

Tropical Villas of Venice Beach : This holiday home rental outside of Osprey Village is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

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Our top choices for Osprey Village holiday rentals

A compact living space with a kitchen, a dining area, and a sofa with cushions.

1. Tiny House Siesta

Sarasota

Staci

includes taxes & fees

1 Nov - 2 Nov

A pool area with a waterfall feature, lounge chairs, and palm trees.

2. Tropical Beach Resorts

South Village

Liliana

includes taxes & fees

22 Oct - 23 Oct

An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

includes taxes & fees

2 Nov - 3 Nov

A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

South Village

Karla

includes taxes & fees

9 Nov - 10 Nov

A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

5. A Beach Retreat

Casey Key

Robin

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

6. SeaSpray Resort

Siesta Key

Rommel

includes taxes & fees

16 Nov - 17 Nov

A wooden structure with a thatched roof overlooking a beach.

7. Casey Key Resort

Casey Key

Greg

includes taxes & fees

28 Oct - 29 Oct

A living room with a red sofa, a glass coffee table, a TV mounted on the wall, and a dining area with a floral tablecloth.

8. Charming cottage for 2 across warm mineral springs park

Warm Mineral Springs

VIKTOR M.

includes taxes & fees

24 Oct - 25 Oct

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Top Osprey Village Hotel Reviews

The Westin Sarasota

10/10 Excellent

"Nice hotel and a pleasant stay."

Embassy Suites by Hilton Sarasota, FL

10/10 Excellent

"This was a short stay while visiting friends in the area and we spent both nights eating and drinking at the restaurant on site. The views were fabulous. The staff were efficient and friendly. There was a small inconvenience at check in but the staff bent over backwards to make amends. I highly recommend this hotel and will be back!"

Cottages at Siesta Key Inn

10/10 Excellent

"The Cottages were sold to Azul Resorts which has another similar location around the corner. The entire complex went through a renovation in December of 2025. Expedia still shows it under the old name, and that was a little confusing when I arrived. It looked very clean and new for the most part. I booked the Studio unit with a King size bed. The bed was comfortable and the pillows were great. There is a 65" TV on the wall. It was exactly the same as the one I have at home which was great because I didn't have to learn how to work it. :-) The location is about 250 ft. from the beach access entrance (#13), which is another 200 foot walking path to the sand. The path leaves you about 150 feet from the water (low tide), and about 100 feet from the water (high tide). So if walking is difficult for you, know that you will walk approximately 550 feet before you can wet your toes in the Gulf of America. Regarding the location, it is about 4 miles South of the Sarasota Village downtown, 3 miles South of the main Sarasota Beach public parking area, but there are plenty of restaurant and tiki bars within 1 or 2 miles of the Azul Resort. The only cons I found were that the pool wasn't heated, and someone operates a chair and umbrella rental service that blocks a huge part of the beach area. There is room to the left of the path, or you can go to the right of the blocked off area. They also leave a small strip in front of the blocked area. We didn't have a problem finding room on d'sand."

Siesta Key Beach Resort and Suites

8/10 Good

"I had a three night stay at this hotel on Siesta Key. Great location, and I walked every where safely alone. Very friendly staff! My comments on the room. - the mattress needs to be replaced in room 102 - a threshold at the door would be nice to keep any critters from crawling into the room. - the dehumidifier in the room makes some very loud sounds, frequently, which woke me often."

Find out more about Osprey Village

Everything you need to know about Osprey Village holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey Village holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey Village holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey Village holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey Village. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey Village holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey Village holiday rentals we have selected for you start as low as €126 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osprey Village rentals

At Expedia, we put the best Osprey Village holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osprey Village rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey Village holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey Village. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in Osprey Village?

Yes, there are holiday rentals close to the most popular sights in Osprey Village, or you can select a more secluded option if you're looking for a relaxing stay.

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

Tropical Villas of Venice Beach: This holiday home rental outside of Osprey Village is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

How many holiday rentals will I find in Osprey Village?

Expedia has 3 holiday rentals for your stay in Osprey Village.

What can I see and do in Osprey Village?

While exploring the area, visit family-friendly sights like Mote Marine Laboratory & Aquarium, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and Turtle Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Osprey Village?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osprey Village. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.

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