Osprey Village Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Osprey Village vacation rentals

Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,271 reviews)
"Wonderful stay!"
United States
Victoria
The price is ￥33,299
￥41,609 total
includes taxes & fees
Feb 1 - Feb 2
Tropical Beach Resorts
Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (253 reviews)
"Great place! "
United States
Michelle
The price is ￥44,600
￥50,398 total
includes taxes & fees
Feb 16 - Feb 17
Kon Tiki Inn
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,244 reviews)
"Very clean, and staff was extremely nice. "
United States
Maribeth
The price is ￥30,889
￥34,905 total
includes taxes & fees
Feb 1 - Feb 2
Hibiscus Suites - Gateway to Siesta Key
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (349 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is ￥15,315
￥35,914 total
includes taxes & fees
Feb 1 - Feb 2
Tiny House Siesta
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,193 reviews)
"Excellent place and location, "
United States
Richard
The price is ￥33,370
￥40,305 total
includes taxes & fees
Feb 2 - Feb 3
Captiva Beach Resort
Interior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.4 out of 10, Exceptional, (13 reviews)
"Property was perfect for the price."
United States
William M.
The price is ￥9,955
￥24,696 total
includes taxes & fees
Mar 1 - Mar 2
Charming cottage for 2 across warm mineral springs park
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (592 reviews)
"The location is ideal, rooms are nice and the owners are extremely accommodating. "
United States
Catherine
A Beach Retreat
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (90 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is ￥59,575
￥67,320 total
includes taxes & fees
Jan 31 - Feb 1
SeaSpray Resort
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38 reviews)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is ￥52,025
￥89,593 total
includes taxes & fees
Feb 12 - Feb 13
Siesta Heron Suites & Villas
Beach nearby, white sand, beach umbrellas, beach towels

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (194 reviews)
"Very charming place! Great location for the beach and restaurants. Would definitely stay again."
United States
Blaine
The Inn On Siesta Key
Living area

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (16 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is ￥15,524
￥36,464 total
includes taxes & fees
Feb 1 - Feb 2
Nestled in North Port. Updated 2 Bed / 1 Bath.
Interior

Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
The price is ￥29,711
￥96,938 total
includes taxes & fees
Feb 8 - Feb 9
Family Fun: Ping Pong, Bbq, Walk to Park Nearby
Beach nearby, beach towels

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (60 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is ￥22,743
￥47,907 total
includes taxes & fees
Feb 1 - Feb 2
Old Floridian cottage in Historic Gulf Village
Fridge, microwave, oven, stovetop

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (28 reviews)
"The property was very clean and conveniently located ."
United States
David
The price is ￥18,772
￥52,306 total
includes taxes & fees
Feb 6 - Feb 7
[lounge like locals] walk to siesta beach +bikes
Fridge, microwave, coffee/tea maker, electric kettle

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (36 reviews)
"This is our 3rd year staying at this property. We love the location and convince of a quiet neighborhood off university road. We also appreciate the updated amenities and the bed topper is a huge plus for us! "
United States
Cecillia C.
The price is ￥14,089
￥30,231 total
includes taxes & fees
Feb 9 - Feb 10
Beautiful University Pines Studio in Sarasota
Fridge, microwave, oven, stovetop

Myakka River

Myakka River
Venice
9.8 out of 10, Exceptional, (18 reviews)
"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 ￥28,331
￥70,054 total
includes taxes & fees
Feb 4 - Feb 5
Myakka River
Terrace/patio

Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available

Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available
Venice Island
9.8 out of 10, Exceptional, (105 reviews)
"Great location and wonderful accommodations. A gem a few blocks walk to the beach. "
United States
Cindi B.
The price is ￥24,441
￥65,640 total
includes taxes & fees
Jan 31 - Feb 1
Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available
On the beach, sun loungers, beach towels

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (69 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
The price is ￥91,578
￥148,108 total
includes taxes & fees
Feb 14 - Feb 15
Direct Beachfront 2BR Cottage on Casey Key!
1 bedroom, desk, iron/ironing board, WiFi

Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath
Bayou Oaks
9.2 out of 10, Wonderful, (43 reviews)
"Excellent place to stay"
United States
garry s.
The price is ￥11,945
￥22,617 total
includes taxes & fees
Feb 8 - Feb 9
Riverside Oasis 1Bed/1Bath
Property grounds

Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen

Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen
Longboat Key
9.8 out of 10, Exceptional, (258 reviews)
"Very clean and “homey”. Access to the beach is so easy and close. Quaint and quiet with great access to the rest of the island. The Host communicated well and made sure our stay was everything we hoped for. "
United States
R. Brian L.
The price is ￥16,677
￥62,274 total
includes taxes & fees
Feb 1 - Feb 2
Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"The staff were great. They helped me as my stay grew longer and longer in the wake of snow travel disruption. They made it easy as I had to extend my stay."
Peter 2-night trip
Posted 2 days ago
Kompose Boutique Hotel

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 in Osprey Village close to Nancy's Consignments, or you can go with a more remote option if you're looking for extra privacy while you relax.

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

Siesta Key Island Rentals: This vacation home rental near Osprey Village comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Osprey Village?

Expedia has 4 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 Nancy's Consignments, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and St. Armands Circle are other popular places to visit in the 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.