Osprey Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Osprey holiday rentals

Beach towels

Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
The price is HK$1,488
HK$3,110 total
includes taxes & fees
10 May - 11 May
Charming Osprey Home
Beach

Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (5 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 HK$1,488
HK$3,110 total
includes taxes & fees
10 May - 11 May
Sunny Coastal Escape
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, (21 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is HK$675
HK$1,707 total
includes taxes & fees
17 Apr - 18 Apr
Nestled in North Port. Updated 2 Bed / 1 Bath.
Interior

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (37 reviews)
"Me and my significant other took a little mini vacation wonderful house. It was very clean very beautiful inside, I like the beach vibes beautiful bedrooms. I recommend anybody to book this place. If I had to go back, I’ll book again. "
United States
Alexus
The price is HK$881
HK$2,566 total
includes taxes & fees
27 Apr - 28 Apr
Mimosa Memories
Beach

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (182 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
The price is HK$1,114
HK$2,861 total
includes taxes & fees
17 Apr - 18 Apr
Paradise Retreat with HEATED POOL-- Need We Say More
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, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is HK$940
HK$2,175 total
includes taxes & fees
5 May - 6 May
Old Floridian cottage in Historic Gulf Village
Beach nearby, sun-loungers, beach towels

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Lido Key
9.8 out of 10, Exceptional, (122 reviews)
"Super clean, perfect location, and cool decor - and, most important, veeerry comfortable beds! We loved our stay! "
United States
Kevin L.
The price is HK$984
HK$2,260 total
includes taxes & fees
23 Apr - 24 Apr
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is HK$899
HK$4,532 total
includes taxes & fees
28 Apr - 29 Apr
Chadwick Cove Resort & Marina
Microwave, oven, stovetop, dishwasher

Centrally Located, Sarasota Home Close To Amish Community

Centrally Located, Sarasota Home Close To Amish Community
Sarasota Springs
10.0 out of 10, Exceptional, (173 reviews)
"Love this place ! Was a great stay!"
United States
Jacob E.
The price is HK$1,214
HK$3,089 total
includes taxes & fees
20 Apr - 21 Apr
Centrally Located, Sarasota Home Close To Amish Community
Beach nearby, sun-loungers, beach towels

Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (72 reviews)
"Great location in Siesta Key Village, can walk to all the shops and restaurants as well as the beach "
United States
Erica S.
The price is HK$1,198
HK$3,047 total
includes taxes & fees
22 Apr - 23 Apr
Siesta Key Village-Suite #3: A Block to the Beach!
TV, fireplace

Luxury House Walking Distance to Ocean - Sleeps 12

Luxury House Walking Distance to Ocean - Sleeps 12
Central Sarasota
9.8 out of 10, Exceptional, (16 reviews)
"Great place perfect location to the marina, and downtown area. Highly recommended thanks "
United States
Domingo B.
The price is HK$1,645
HK$3,713 total
includes taxes & fees
4 May - 5 May
Luxury House Walking Distance to Ocean - Sleeps 12
Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (269 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
The price is HK$934
HK$1,055 total
includes taxes & fees
5 May - 6 May
Kon Tiki Inn
Fridge, microwave, oven, stovetop

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (23 reviews)
"Fun place "
United States
Maureen
The price is HK$879
HK$2,090 total
includes taxes & fees
10 May - 11 May
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
Beach

Lakefront Condo · Pools & Hot Tubs · IMG Academy 5 Min · Anna Maria Beach Island

Lakefront Condo · Pools & Hot Tubs · IMG Academy 5 Min · Anna Maria Beach Island
Bradenton
9.8 out of 10, Exceptional, (118 reviews)
"Perfect spot and host "
United States
Dee B.
The price is HK$917
HK$2,395 total
includes taxes & fees
27 Apr - 28 Apr
Lakefront Condo · Pools & Hot Tubs · IMG Academy 5 Min · Anna Maria Beach Island
On the beach

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (77 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
The price is HK$1,175
HK$2,403 total
includes taxes & fees
23 Apr - 24 Apr
Beachfront Studio – Cabana #5B by RVA
2 bedrooms, iron/ironing board, WiFi, bed sheets

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is HK$1,162
HK$2,961 total
includes taxes & fees
19 Apr - 20 Apr
[escape to paradise] siesta key beach getaway
Beach nearby

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Breathtaking view- super clean. Easy access. Perfect spot for a few days away with my husband."
United States
Ellen L.
The price is HK$1,439
HK$3,290 total
includes taxes & fees
30 Apr - 1 May
Best views of the beach from your balcony Unit 301
Beach

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is HK$1,285
HK$2,859 total
includes taxes & fees
20 Apr - 21 Apr
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Beach

Lavish Condo! Heated Pools & Hot Tubs · IMG Academy 5 Min · Anna Maria Island

Lavish Condo! Heated Pools & Hot Tubs · IMG Academy 5 Min · Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (124 reviews)
"We enjoyed our stay. Is as shown in pictures and description. "
United States
Erin M.
The price is HK$917
HK$2,505 total
includes taxes & fees
10 May - 11 May
Lavish Condo! Heated Pools & Hot Tubs · IMG Academy 5 Min · Anna Maria Island
On the beach, beach umbrellas

Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Clean, cozy and right in the beach!! Was a perfect little getaway! "
United States
Michelle M.
The price is HK$1,222
HK$2,553 total
includes taxes & fees
20 Apr - 21 Apr
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"very good "
Walter 2-night trip
Posted 5 hours ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Search for holiday rentals in Osprey on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

  • View our selection of featured holiday rentals in Osprey
  • Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

Look no further and take a look at our great range of rental properties in Osprey!

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 lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

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

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with free 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 are there in Osprey?

With 19 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.