Osprey Holiday Rentals from NZ$298: Search Short-Term Rentals

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

Tropical Villas of Venice Beach : This holiday home rental outside of Osprey 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 holiday rentals

An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees visible in the foreground.

1. Charming Osprey Home

Bay Acres

Diane S.

includes taxes & fees

11 Nov - 12 Nov

An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees in the foreground.

2. Sunny Coastal Escape

Bay Acres

Jennifer A.

includes taxes & fees

24 Nov - 25 Nov

A tented accommodation with a bed, pillows, a desk, and chairs.

3. Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Sarasota

includes taxes & fees

18 Nov - 19 Nov

A tented accommodation with a central bed, bedside tables, a hanging light fixture, and a patterned floor.

4. Charming Secluded Tented Cabin in Sarasota, Florida

Sarasota

includes taxes & fees

18 Nov - 19 Nov

5. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Sarasota

includes taxes & fees

18 Nov - 19 Nov

A tent with two chairs and a checkered mat in a forest.

6. Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Sarasota

includes taxes & fees

18 Nov - 19 Nov

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

7. Tropical Beach Resorts

South Village

Christine

includes taxes & fees

12 Nov - 13 Nov

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

8. A Beach Retreat

Casey Key

Robin

includes taxes & fees

6 Dec - 7 Dec

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

9. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

includes taxes & fees

18 Nov - 19 Nov

A compact living space with a sofa, a television, a ceiling fan, and a door.

10. Tiny House Siesta

Sarasota

Staci

includes taxes & fees

18 Nov - 19 Nov

A beach with white sand, wooden beach chairs, and a clear blue sky.

11. Captiva Beach Resort

South Village

Bob

includes taxes & fees

19 Nov - 20 Nov

A modern kitchen with a stainless steel sink, a dining area with a table and chairs, and a living room with a sofa and a TV.

12. Oceanfront home

Vamo

Ashley H.

includes taxes & fees

15 Nov - 16 Nov

A wooden structure with a thatched roof overlooking a beach.

13. Casey Key Resort

Casey Key

Jamie

includes taxes & fees

10 Dec - 11 Dec

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.

14. SeaSpray Resort

Siesta Key

Geraldine

includes taxes & fees

11 Nov - 12 Nov

A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

15. The Dolphin

Nokomis

daniel

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a bed, a dresser, a television, a painting, and a chair.

16. 2 Miles to Siesta Key

Gulf Gate Estates

Keith K.

A hotel room with a bed, a round table with chairs, a ceiling fan, and a door.

17. Bright & Beachy–Beach Club Siesta Key 100A by RVA

South Village

Evan C.

includes taxes & fees

4 Dec - 5 Dec

A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

18. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

South Village

maureen p.

includes taxes & fees

11 Nov - 12 Nov

A wooden boardwalk leading to a beach with a clear blue sky.

19. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key

kelly h.

includes taxes & fees

11 Nov - 12 Nov

A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

20. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

South Village

James J.

includes taxes & fees

11 Nov - 12 Nov

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Find holiday rentals that suit your style

Top Osprey Hotel Reviews

A pathway flanked by palm trees and a building with a covered patio area.

Casey Key Resorts - Mainland

Osprey

10/10 Excellent

Tabra

Tropical Beach Resorts

South Village

8/10 Good

Inkredible me

A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.

Comfort Suites Sarasota - Siesta Key

Sarasota

10/10 Excellent

Ranjana

A rooftop bar with outdoor seating, a pool, and a view of the sea.

Art Ovation Hotel, Autograph Collection

Central Sarasota

10/10 Excellent

Patrick

A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.

Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

10/10 Excellent

Triin

Find out more about Osprey

Everything you need to know about Osprey 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 holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey. 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 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 holiday rentals we have selected for you start as low as NZ$298 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey 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 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 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. 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 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 top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

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

Tropical Villas of Venice Beach: This holiday home rental outside of Osprey 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 are there in Osprey?

With 13 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?

Turtle Beach and Nokomis Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. 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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Activities in Siesta Key
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Osprey Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osprey holiday rentals

1. Charming Osprey Home

2. Sunny Coastal Escape

3. Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

4. Charming Secluded Tented Cabin in Sarasota, Florida

5. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

6. Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

7. Tropical Beach Resorts

8. A Beach Retreat

9. Hibiscus Suites - Gateway to Siesta Key

10. Tiny House Siesta

11. Captiva Beach Resort

12. Oceanfront home

13. Casey Key Resort

14. SeaSpray Resort

15. The Dolphin

16. 2 Miles to Siesta Key

17. Bright & Beachy–Beach Club Siesta Key 100A by RVA

18. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

19. Casey Key Beachfront Escape: Charming 1BR Cottage

20. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Find holiday rentals that suit your style

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

10/10 Excellent

Find out more about Osprey

Osprey holiday rentals: An excellent choice for every season

How to find incredible deals on Osprey rentals

Frequently Asked Questions

Can I find holiday rentals in Osprey?

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

How many holiday rentals are there in Osprey?

What’s there to see and do in Osprey?

What’s a holiday rental in Osprey like?

Explore a world of travel with Expedia