Osprey Village Holiday Rentals - Holiday Homes in Osprey Village

Q: What's the top vacation rental that Osprey Village has to offer?

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

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Our top choices for Osprey Village vacation rentals

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

1. Tiny House Siesta

Sarasota

Staci

P12,437 total

includes taxes & fees

Oct 23 - Oct 24

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

2. Tropical Beach Resorts

South Village

Liliana

P11,543 total

includes taxes & fees

Oct 21 - Oct 22

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

3. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

P9,433 total

includes taxes & fees

Oct 22 - Oct 23

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

P13,257 total

includes taxes & fees

Oct 18 - Oct 19

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

5. A Beach Retreat

Casey Key

Robin

P13,130 total

includes taxes & fees

Nov 4 - Nov 5

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

P15,949 total

includes taxes & fees

Nov 16 - Nov 17

A wooden structure with a thatched roof overlooking a beach.

7. Casey Key Resort

Casey Key

Greg

P14,457 total

includes taxes & fees

Oct 28 - Oct 29

8. The Inn On Siesta Key

Siesta Key

Stephen

P19,688 total

includes taxes & fees

Oct 18 - Oct 19

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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

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

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Frequently asked questions

Can I find a vacation rental in Osprey Village?

Yes, we give you a choice of vacation rentals close to popular local attractions in Osprey Village, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Osprey Village has to offer?

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

How many vacation rentals will I find in Osprey Village?

Expedia has 3 vacation 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 larger area.

What are vacation rentals like in Osprey Village?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Osprey Village. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.

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