Osprey Village Holiday Rentals

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Our top choices for Osprey Village holiday rentals

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (247)
"Lovely decor, very clean"
United States
Frederick
The price is NZ$459
includes taxes & fees
20 Jan - 21 Jan 2026
Kon Tiki Inn
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
The price is NZ$300
includes taxes & fees
1 Jan - 2 Jan 2026
Charming cottage for 2 across warm mineral springs park
9.0 out of 10, Wonderful, (9)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is NZ$270
includes taxes & fees
22 Dec - 23 Dec
#3 Small house walking distance to Warm Mineral Spring
10.0 out of 10, Exceptional, (12)
"My husband's stay here was perfect for some time spent with older aunts/uncles in the area. This gave them a place to unwind, relax and such in between the visits. He said it was a very nice place to stay"
United States
Debbie S.
The price is NZ$428
includes taxes & fees
24 Dec - 25 Dec
Nestled in North Port. Updated 2 Bed / 1 Bath.

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5162)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is NZ$288
includes taxes & fees
22 Dec - 23 Dec
Tropical Beach Resorts
2.5 star property
8.6 out of 10, Excellent, (2215)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key

Holiday Home in Olde Englewood Village

Old Floridian cottage in Historic Gulf Village
9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
The price is NZ$513
includes taxes & fees
22 Dec - 23 Dec
Old Floridian cottage in Historic Gulf Village

Apartment in Olde Englewood Village

Newly renovated only minutes away from the beach!!
9.6 out of 10, Exceptional, (58)
"Clean, comfortable, everything you need! Owner is great!"
United States
Cheryl L.
The price is NZ$495
includes taxes & fees
31 Dec - 1 Jan 2026
Newly renovated only minutes away from the beach!!

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1175)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort

Holiday Home in Venice

Myakka River
9.8 out of 10, Exceptional, (18)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is NZ$798
includes taxes & fees
22 Dec - 23 Dec
Myakka River

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is NZ$707
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas

Holiday Home in South Venice

Mimosa Memories
9.4 out of 10, Exceptional, (30)
"Nice quiet home , very clean. "
United States
David M.
The price is NZ$578
includes taxes & fees
22 Dec - 23 Dec
Mimosa Memories
8.4 out of 10, Very good, (12)
"Great place to stay. "
United States
Scott
The price is NZ$760
includes taxes & fees
28 Dec - 29 Dec
Coastal duplex with private beach access & deck - dog-friendly
9.8 out of 10, Exceptional, (35)
"Super clean rental… exactly as described, great location close to everything"
United States
Randy S.
The price is NZ$349
includes taxes & fees
21 Jan - 22 Jan 2026
Beautiful University Pines Studio in Sarasota

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is NZ$378
includes taxes & fees
23 Dec - 24 Dec
Tiny House Siesta
9.2 out of 10, Wonderful, (69)
"The Cottage is simple and in need of a few updates, but it is a beach cottage and the salt air is not kind. Overall, the location is fantastic, the Cottage is clean and comfortable and our stay was great."
United States
Bob T.
The price is NZ$717
includes taxes & fees
22 Dec - 23 Dec
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
9.2 out of 10, Wonderful, (36)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
The price is NZ$300
includes taxes & fees
31 Dec - 1 Jan 2026
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Apartment in Siesta Key

The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (346)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House

Condo in Bayou Oaks

Casa Azul 2Bed/1Bath
9.6 out of 10, Exceptional, (69)
"Perfect accomodarions. "
United States
Anonymous traveller
Casa Azul 2Bed/1Bath

Apartment in Gulf Gate Estates

2 Miles to Siesta Key
10.0 out of 10, Exceptional, (18)
"Host was super attentive and location is terrific "
United States
Leon P.
The price is NZ$308
includes taxes & fees
26 Dec - 27 Dec
2 Miles to Siesta Key
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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Top Osprey Village Hotel Reviews

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 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 in Osprey Village close to Nancy's Consignments, 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?

Siesta Key Island Rentals: This holiday home rental outside of Osprey Village 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 will I find in Osprey Village?

Expedia has 4 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 Nancy's Consignments, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and Oscar Scherer State Park 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.