Osprey Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Osprey holiday rentals

Beach

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 HK$2,010
HK$3,805 total
includes taxes & fees
30 Mar - 31 Mar
Sunny Coastal Escape
Beach towels

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 HK$2,207
HK$4,006 total
includes taxes & fees
23 Mar - 24 Mar
Charming Osprey Home
Living area

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 HK$876
HK$1,941 total
includes taxes & fees
7 Mar - 8 Mar
Tiny House Siesta
Exterior

#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 HK$547
HK$1,305 total
includes taxes & fees
6 Mar - 7 Mar
#3 Small house walking distance to Warm Mineral Spring
Interior

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 HK$509
HK$1,262 total
includes taxes & fees
1 Mar - 2 Mar
Charming cottage for 2 across warm mineral springs park
Interior

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 HK$880
HK$2,548 total
includes taxes & fees
2 Mar - 3 Mar
Mimosa Memories
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, (17 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is HK$981
HK$2,075 total
includes taxes & fees
1 Mar - 2 Mar
Nestled in North Port. Updated 2 Bed / 1 Bath.
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, (39 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
The price is HK$609
HK$1,508 total
includes taxes & fees
23 Mar - 24 Mar
Beautiful University Pines Studio in Sarasota
1 bedroom, desk, free WiFi, bed sheets

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 HK$586
HK$1,349 total
includes taxes & fees
21 Mar - 22 Mar
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
On the beach

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.
The price is HK$1,181
HK$2,392 total
includes taxes & fees
3 Mar - 4 Mar
Beachfront Studio – Cabana #5B by RVA
1 bedroom, desk, iron/ironing board, WiFi

Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath
Bayou Oaks
9.2 out of 10, Wonderful, (45 reviews)
"Excellent place to stay"
United States
garry s.
The price is HK$665
HK$1,217 total
includes taxes & fees
22 Mar - 23 Mar
Riverside Oasis 1Bed/1Bath
Property grounds

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 HK$1,317
HK$3,072 total
includes taxes & fees
4 Mar - 5 Mar
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
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, (27 reviews)
"Clean and comfortable. "
United States
Laney
The price is HK$4,430
HK$7,383 total
includes taxes & fees
24 Mar - 25 Mar
[escape to paradise] siesta key beach getaway
Beach nearby

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
1 bedroom, free WiFi, bed sheets

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 HK$931
HK$1,464 total
includes taxes & fees
3 Mar - 4 Mar
2 Miles to Siesta Key
On the beach

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
Longboat Key
7.8 out of 10, Good, (11 reviews)
"Amazing property with direct beach access. "
United States
maria m.
The price is HK$1,556
HK$2,723 total
includes taxes & fees
3 Mar - 4 Mar
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
Sun-loungers, beach towels

Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.

Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.
Nokomis
9.4 out of 10, Exceptional, (35 reviews)
"Our stay was lovely and beautiful l. Everything was nice and clean and anywhere we went was only 5 minutes away so the location and neighborhood was great! "
United States
Chelsey H.
The price is HK$1,416
HK$3,114 total
includes taxes & fees
28 Mar - 29 Mar
Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.
On the beach

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (74 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The condo was clean and had all that we needed for our two night stay. Loved it will be back again... just a little walk to the beach and some he pool was very nice as well."
United States
Nancy C.
The price is HK$1,400
HK$2,859 total
includes taxes & fees
10 Mar - 11 Mar
Newly Renovated 1BR – Cabana Beach #5 RVA
Beach nearby, sun-loungers, beach towels

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 HK$1,009
HK$1,552 total
includes taxes & fees
11 Mar - 12 Mar
Two Miles to Siesta Key
Beach

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
7.8 out of 10, Good, (7 reviews)
"Great locale right on the beach "
United States
Carole
The price is HK$1,472
HK$2,868 total
includes taxes & fees
11 Mar - 12 Mar
Beachfront Bliss on Longboat Key- Steps to the sand
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Location, convenient, pool area."
JONI 2-night trip
Posted 1 day 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
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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 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.