Holiday Rentals in Osprey

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Our top choices for Osprey holiday rentals

Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (3 reviews)
"Great location for exploring north & south! House was very clean and comfy. We appreciated the excellent communication with our nice host, Lynn."
United States
Kaja F.
The price is €415
includes taxes & fees
29 Mar - 30 Mar
Sunny Coastal Escape

Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (1 review)
"Upon entering the property, we felt it was clean, bright and very welcoming. We loved the decor and the nice spaces in this two bedroom, two bath home. We thought the location was perfect, right across the main street is Walmart for quick grocery items, and we liked the amenities including a kettle for hot tea, a coffeemaker and a fully equipped kitchen! We would have liked to have more than two beach towels, but we made do with two. The laundry room was convenient for washing clothes and did...
United States
Van-Ha N.
The price is €444
includes taxes & fees
25 Mar - 26 Mar
Charming Osprey Home

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (352 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is €210
includes taxes & fees
2 Mar - 3 Mar
Tiny House Siesta

#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring
Warm Mineral Springs
9.2 out of 10, Wonderful, (13 reviews)
"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 €146
includes taxes & fees
1 Mar - 2 Mar
#3 Small house walking distance to Warm Mineral Spring

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (14 reviews)
"Property was perfect for the price."
United States
William M.
The price is €141
includes taxes & fees
1 Mar - 2 Mar
Charming cottage for 2 across warm mineral springs park

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, (17 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
Nestled in North Port. Updated 2 Bed / 1 Bath.

Myakka River

Myakka River
Venice
9.8 out of 10, Exceptional, (19 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 €394
includes taxes & fees
27 Feb - 28 Feb
Myakka River

Mimosa Memories

Mimosa Memories
South Venice
9.4 out of 10, Exceptional, (32 reviews)
"Nice quiet home , very clean. "
United States
David M.
The price is €278
includes taxes & fees
2 Mar - 3 Mar
Mimosa Memories

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (16 reviews)
"Great place and location "
United States
Cathy
The price is €516
includes taxes & fees
27 Feb - 28 Feb
Chadwick Cove Resort & Marina

Home in quiet Bird Sanctuary Neighborhood, close to Beach

Home in quiet Bird Sanctuary Neighborhood, close to Beach
South Venice
9.6 out of 10, Exceptional, (16 reviews)
"We loved this place! It was convenient to everything we liked to do and the perfect size for my husband and I. The bed was comfortable and everything was very clean. "
United States
Melissa N.
The price is €407
includes taxes & fees
5 Mar - 6 Mar
Home in quiet Bird Sanctuary Neighborhood, close to Beach

2 Miles to Siesta Key

2 Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (22 reviews)
"Had a great stay! "
United States
Keith K.
The price is €162
includes taxes & fees
3 Mar - 4 Mar
2 Miles to Siesta Key

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (37 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 €171
includes taxes & fees
12 Mar - 13 Mar
Beautiful University Pines Studio in Sarasota

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (74 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
Beachfront Studio – Cabana #5B by RVA

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Sabal Harbour
9.8 out of 10, Exceptional, (27 reviews)
"Everything was great!"
United States
Lisa and Colin M.
The price is €388
includes taxes & fees
10 Mar - 11 Mar
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

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, (45 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
The price is €500
includes taxes & fees
2 Mar - 3 Mar
Siesta Key Village-Suite #1: A block to the Beach!

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Bayshore Gardens
9.2 out of 10, Wonderful, (37 reviews)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
The price is €150
includes taxes & fees
27 Mar - 28 Mar
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Bradenton
9.8 out of 10, Exceptional, (136 reviews)
"Only went to pool 1 day as spent most of the time at the beach its a nice area with lots to do and lots of nice walks and great beaches "
United Kingdom
David C.
*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

Two Miles to Siesta Key

Two Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (46 reviews)
"Terry was a great host. The apartment was very comfortable and had everything we needed for our short stay in Sarasota. Would stay here again."
United States
Robert C.
The price is €163
includes taxes & fees
11 Mar - 12 Mar
Two Miles to Siesta Key

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Sarasota
9.6 out of 10, Exceptional, (14 reviews)
"We had a lovely week in this property and even saw some dolphins swimming by!"
United States
Hilda H.
Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (27 reviews)
"Clean and comfortable. "
United States
Laney
The price is €354
includes taxes & fees
8 Mar - 9 Mar
[escape to paradise] siesta key beach getaway
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 Hotel Reviews

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, apart-hotels, 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 €210 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?

Siesta Heron Suites & Villas: This holiday home rental outside of Osprey is located on the waterfront, and has an outdoor pool, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

How many holiday rentals are there in Osprey?

With 18 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?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. 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.