Osprey Village Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Osprey Village holiday rentals

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

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,062 reviews)
"Great resort and location!"
United States
Christine
The price is NZ$328
includes taxes & fees
16 Nov - 17 Nov
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,486 reviews)
"This place was perfect!"
United States
Kat
The price is NZ$279
includes taxes & fees
16 Nov - 17 Nov
Hibiscus Suites - Gateway to Siesta Key
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

3. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (701 reviews)
"Enjoyed our stay"
United States
Robin
The price is NZ$377
includes taxes & fees
6 Dec - 7 Dec
A Beach Retreat
A beach with white sand, wooden beach chairs, and a clear blue sky.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,337 reviews)
"Great location that's very close to the beach, large and clean room with a kitchenette, and very helpful and friendly staff. Loved our stay here!"
United States
Bob
The price is NZ$346
includes taxes & fees
17 Nov - 18 Nov
Captiva Beach Resort
A wooden structure with a thatched roof overlooking a beach.

5. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (288 reviews)
"My boyfriend and I had a wonderful time. Easy late check in. Nice clean room. Property beautiful. Private beach beautiful. We definitely plan to come back and have family join."
United States
Jamie
The price is NZ$383
includes taxes & fees
10 Dec - 11 Dec
Casey Key Resort
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

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (209 reviews)
"The room was clean and had all of the necessities. The place was adorable and the location is great!"
United States
Dolores
The price is NZ$621
includes taxes & fees
24 Nov - 25 Nov
SeaSpray Resort
A compact living space with a sofa, a television, a ceiling fan, and a door.

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (392 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is NZ$369
includes taxes & fees
18 Nov - 19 Nov
Tiny House Siesta
A pathway with wooden posts and ropes, leading to a building with a sign indicating a nautical room.

8. Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (320 reviews)
"Debbie and Sean are excellent hosts. Very clean, very comfortable, very quiet. Pet friendly, which is awesome also. Great location also just a couple miles from downtown or the beach.."
United States
Joseph
The price is NZ$289
includes taxes & fees
16 Nov - 17 Nov
Kon Tiki Inn
A wooden boardwalk leading to a beach with a clear blue sky.

9. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.6 out of 10, Exceptional, (137 reviews)
"Cute little cottage right on the beach. Doesn’t get any better than that."
United States
kelly h.
The price is NZ$869
includes taxes & fees
23 Nov - 24 Nov
Casey Key Beachfront Escape: Charming 1BR Cottage
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

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

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is NZ$462
includes taxes & fees
17 Nov - 18 Nov
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

11. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
The price is NZ$479
includes taxes & fees
15 Nov - 16 Nov
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
A beach with clear turquoise water and gentle waves.

12. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (55 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
The price is NZ$446
includes taxes & fees
15 Nov - 16 Nov
Siesta Key, Sea Horse Villa, Pool. Daily rentals
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.

13. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (94 reviews)
"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."
United States
Ashley H.
The price is NZ$958
includes taxes & fees
15 Nov - 16 Nov
Oceanfront home
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

14. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is NZ$410
includes taxes & fees
15 Nov - 16 Nov
The Dolphin
A beach with a wooden picnic table, palm trees, and a clear blue sea.

15. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (192 reviews)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

16. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"Great beach! "
United States
Annie B.
The price is NZ$719
includes taxes & fees
15 Nov - 16 Nov
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

17. 2BR Beach & Trolley–Beach Club Siesta 204B by RVA

2BR Beach & Trolley–Beach Club Siesta 204B by RVA
South Village
8.6 out of 10, Excellent, (48 reviews)
"Was exactly as advertised. When I needed help the hosts were responsive. I have stayed there twice. Would stay again."
United States
Ben B.
The price is NZ$674
includes taxes & fees
15 Nov - 16 Nov
2BR Beach & Trolley–Beach Club Siesta 204B by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"We enjoyed it. All was as described"
United States
Pamela S.
The price is NZ$500
includes taxes & fees
15 Nov - 16 Nov
Bright & Beachy–Beach Club Siesta Key 100A by RVA
A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

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

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Great stay."
United States
James J.
The price is NZ$395
includes taxes & fees
17 Nov - 18 Nov
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
A beach with clear blue water, gentle waves, and a distant sailboat.

20. Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (48 reviews)
"Just as expected and great communication"
United States
Kris
The price is NZ$691
includes taxes & fees
16 Nov - 17 Nov
Siesta Key Village-Suite #1: A block to the Beach!
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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Find holiday rentals that suit your style

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Top Osprey Village Hotel Reviews

A hotel room with two beds, a TV, a microwave, and a desk with a lamp.
Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota

10/10 Excellent

Excellent hotel, spacious good rooms, fast internet, good amenities, free onsite parking, good hot breakfast...
Australia
Ranjana
Reviewed November 13, 2024
Comfort Suites Sarasota - Siesta Key

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, 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 NZ$279 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.