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Holiday homes in Osprey (Page 3)

Enjoy your stay and find the best Holiday homes in Osprey at affordable prices

Searching for a holiday home in Osprey (Florida)? Explore a great selection of vacation homes in Osprey to find the one that best fits to your needs, starting from $62.66 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Osprey and region (20 miles)
Midnight Cove 6327 #725 in Sarasota, USA

Midnight Cove 6327 #725

Holiday home in Sarasota near Osprey, Florida , 6327 Midnight Pass Road
Midnight Cove 6327 #725 is located in Sarasota, 2.6 km from Siesta Key Beach, 2.8 km from Turtle Beach, as well as 18 km from John and Mable Ringling ...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool
  • TV

no reviews

from $210.17 Show details »

4 miles to Siesta Key Beach #1 in America in Sarasota, USA

4 miles to Siesta Key Beach #1 in Americ...

Holiday home in Sarasota near Osprey, Florida , 3240 Williamsburg Street
Offering garden views, 4 miles to Siesta Key Beach #1 in America is an accommodation located in Sarasota, 17 km from John and Mable Ringling Museum of...
  • Parking

Fabulous 28 Reviews 8.6

from $255.00 Show details »

Breezy Sarasota Home with Private Pool Near Beach! in Sarasota, USA

Breezy Sarasota Home with Private Pool N...

Holiday home in Sarasota near Osprey, Florida
Within 17 km of John and Mable Ringling Museum of Art and 17 km of The John and Mable Ringling Museum of Art, Home with Heated Pool - 2 Miles to Siest...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $351.29 Show details »

Florida Home 3 Mi to Siesta Key, Walk to Gulf Gate in Sarasota, USA

Florida Home 3 Mi to Siesta Key, Walk to...

Holiday home in Sarasota near Osprey, Florida
Set in Sarasota, 17 km from John and Mable Ringling Museum of Art, 17 km from The John and Mable Ringling Museum of Art and 12 km from Sarasota Opera,...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $286.29 Show details »

Crescent Arms 105N in Sarasota, USA

Crescent Arms 105N

Holiday home in Sarasota near Osprey, Florida , 6310 Midnight Pass Road, 105N
Featuring accommodation with a private pool, sea view and a patio, Crescent Arms 105N is located in Sarasota.
  • Parking
  • Family rooms
  • Allergy-free room
  • Outdoor pool
  • Swimming pool

Good 14 Reviews 7.8

from $240.00 Show details »

Crescent Arms Condominiums in Siesta Key, USA

Crescent Arms Condominiums

Holiday home in Siesta Key near Osprey, Florida , 6312 Midnight Pass Rd. Unit Number 603 S
Featuring an outdoor swimming pool, a shared lounge, and a terrace, Crescent Arms Condominiums provides accommodation in Siesta Key with free WiFi and...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 9 Reviews 9.0

from $252.71 Show details »

NEW Completely remodeled villa with beach and heated pool access in Sarasota, USA

NEW Completely remodeled villa with beac...

Villa in Sarasota near Osprey, Florida , 6300 Midnight Pass Rd
NEW Completely remodeled villa with beach and heated pool access is situated in Sarasota, 2.3 km from Siesta Key Beach, 2.7 km from Turtle Beach, and ...
  • Parking
  • Fitness centre

no reviews

from $228.00 Show details »

Crystal Sands & Dreams in Sarasota, USA

Crystal Sands & Dreams

Holiday home in Sarasota near Osprey, Florida
Crystal Sands & Dreams is a beachfront property located in Sarasota, 2.3 km from Siesta Key Beach and 2.7 km from Turtle Beach.
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $258.15 Show details »

Charming Nokomis Home Walk to Beach! in Nokomis, USA

Charming Nokomis Home Walk to Beach!

Holiday home in Nokomis near Osprey, Florida
Located in Nokomis, 500 metres from Nokomis Beach, less than 1 km from North Jetty Beach and 33 km from John and Mable Ringling Museum of Art, Nokomis...
  • Parking

no reviews

from $212.67 Show details »

Sarasota - Coastal Reflections 2843 in Sarasota, USA

Sarasota - Coastal Reflections 2843

Holiday home in Sarasota near Osprey, Florida , 2843 New England Street
Featuring accommodation with a private pool, Sarasota - Coastal Reflections 2843 is set in Sarasota.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $264.61 Show details »

House by Siesta Key in Sarasota, USA

House by Siesta Key

Holiday home in Sarasota near Osprey, Florida , 3328 Clark Road
Set in Sarasota, 17 km from The John and Mable Ringling Museum of Art and 11 km from Sarasota Opera, Entire Home 3 mins Siesta Key & 5 mins to Downtow...
  • Parking
  • Family rooms

Good 5 Reviews 7.2

from $152.60 Show details »

Entire Home by Siesta Key/closed to downtown in Sarasota, USA

Entire Home by Siesta Key/closed to down...

Holiday home in Sarasota near Osprey, Florida , 3330 Clark Road
Set in Sarasota, 17 km from The John and Mable Ringling Museum of Art, 11 km from Sarasota Opera and 11 km from Marina Jack Restaurant and Marina, Ent...
  • Parking
  • Family rooms

no reviews

from $118.33 Show details »

Discover the beauty of Siesta Key at Siesta Villa Whispering Palms in Siesta Key, USA

Discover the beauty of Siesta Key at Sie...

Villa in Siesta Key near Osprey, Florida , 1331 Moonmist Drive
Discover the beauty of Siesta Key at Siesta Villa Whispering Palms in Siesta Key features accommodation with free WiFi, 2.3 km from Siesta Key Beach, ...
  • Parking

no reviews

from $355.53 Show details »

Moonmist Fish Tales in Siesta Key, USA

Moonmist Fish Tales

Holiday home in Siesta Key near Osprey, Florida
Situated 2.2 km from Siesta Key Beach, 18 km from John and Mable Ringling Museum of Art and 18 km from The John and Mable Ringling Museum of Art, Moon...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $210.55 Show details »

Recently Updated Cozy Siesta Key Beach Villa in Siesta Key, USA

Recently Updated Cozy Siesta Key Beach V...

Holiday home in Siesta Key near Osprey, Florida , 1269 Moonmist Circle
Recently Updated Cozy Siesta Key Beach Villa is located in Siesta Key, 2.1 km from Siesta Key Beach, 18 km from John and Mable Ringling Museum of Art,...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $201.00 Show details »

New York Avenue Rancher in Sarasota, USA

New York Avenue Rancher

Holiday home in Sarasota near Osprey, Florida , 5710 New York Avenue
New York Avenue Rancher, a property with a terrace, is located in Sarasota, 17 km from The John and Mable Ringling Museum of Art, 12 km from Sarasota ...
  • Parking
  • Pets allowed

Fabulous 5 Reviews 8.6

from $218.68 Show details »

Classic Sarasota Home Less Than 4 Mi to Public Beach in Sarasota, USA

Classic Sarasota Home Less Than 4 Mi to...

Holiday home in Sarasota near Osprey, Florida
Located 18 km from The John and Mable Ringling Museum of Art, 12 km from Sarasota Opera and 13 km from Marina Jack Restaurant and Marina, Classic Sara...
  • Parking

Good 2 Reviews 7.5

from $205.00 Show details »

Bay Oaks - 6157 #E01 in Siesta Key, USA

Bay Oaks - 6157 #E01

Holiday home in Siesta Key near Osprey, Florida , 6157 Midnight Pass Road
Situated 2 km from Siesta Key Beach, 18 km from John and Mable Ringling Museum of Art and 18 km from The John and Mable Ringling Museum of Art, Bay Oa...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Okay 15 Reviews 5.7

from $181.35 Show details »

Bay Oaks C Ground Floor in Siesta Key, USA

Bay Oaks C Ground Floor

Holiday home in Siesta Key near Osprey, Florida , 6157 Midnight Pass Rd
Bay Oaks C Ground Floor is located in Siesta Key, 2 km from Siesta Key Beach, 18 km from John and Mable Ringling Museum of Art, and 18 km from The Joh...
  • Parking
  • Swimming pool
  • Swimming Pool

Fabulous 2 Reviews 9.0

from $185.39 Show details »

NEW Updated Siesta Key Vacation Rental with Heated Pool Access in Siesta Key, USA

NEW Updated Siesta Key Vacation Rental w...

Holiday home in Siesta Key near Osprey, Florida , 6157 Midnight Pass Road
Set in Siesta Key, 400 metres from Crescent Beach, NEW Updated Siesta Key Vacation Rental with Heated Pool Access offers accommodation with a garden, ...
  • Parking
  • Fitness centre
  • Spa and wellness centre
  • Swimming pool
  • Swimming Pool

Fabulous 1 Reviews 9.0

from $212.51 Show details »

Bay Oaks Ground Floor in Siesta Key, USA

Bay Oaks Ground Floor

Holiday home in Siesta Key near Osprey, Florida
Bay Oaks Ground Floor is situated in Siesta Key, 2 km from Siesta Key Beach, 18 km from John and Mable Ringling Museum of Art, as well as 18 km from T...
  • Parking
  • Swimming pool
  • Swimming Pool
  • TV
  • Air conditioning

Pleasant 1 Reviews 6.0

from $197.54 Show details »

Bay Oaks, 4th floor corner - elevator in Siesta Key, USA

Bay Oaks, 4th floor corner - elevator

Holiday home in Siesta Key near Osprey, Florida
Bay Oaks, 4th floor corner - elevator is located in Siesta Key, 2 km from Siesta Key Beach, 18 km from John and Mable Ringling Museum of Art, as well ...
  • Parking
  • Swimming pool
  • Swimming Pool

Pleasant 1 Reviews 6.0

from $145.27 Show details »

Sarasota Oasis,Charming Home, Heated Saltwater Pool, Screened Pool Area, Private Fencing, Near Siesta Key & Crescent Beach in Sarasota, USA

Sarasota Oasis,Charming Home, Heated Sal...

Holiday home in Sarasota near Osprey, Florida , 2469 Britannia Road
Located in Sarasota, 15 km from John and Mable Ringling Museum of Art and 15 km from The John and Mable Ringling Museum of Art, Great Renovated Vacati...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 3 Reviews 7.3

from $206.67 Show details »

Siesta Key Bay View in Siesta Key, USA

Siesta Key Bay View

Villa in Siesta Key near Osprey, Florida , 1232 Derby Lane
Featuring free bikes, an outdoor swimming pool, and a garden, Siesta Key/ Derby Bay features accommodation in Siesta Key with free WiFi and sea views.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

Good 62 Reviews 7.6

from $290.00 Show details »

Beautiful property on Siesta Key in Siesta Key, USA

Beautiful property on Siesta Key

Villa in Siesta Key near Osprey, Florida , 1234 Derby Lane
Featuring pool views, Beautiful property on Siesta Key offers accommodation with an outdoor swimming pool, a terrace and a tennis court, around 500 me...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 37 Reviews 8.6

from $204.00 Show details »

Number of Holiday homes in Osprey 282
Number of guest ratings 1240
Average price per night $387.60
Lowest price per night $62.66
Highest price per night $1.286.88

Most popular Holiday-homes in Osprey

The most popular Holiday-homes in Osprey based on average guest rating (Top 10).

Cheapest Holiday-homes in Osprey

The cheapest Holiday-homes in Osprey based on room rate per night (Top 10).

Most booked Holiday-homes in Osprey

The most booked Holiday-homes in Osprey based on popularity with guests (Top 10).

Holiday homes in Osprey (Florida), comfortable and familiar

Staying in a holiday or vacation home in Osprey can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Osprey for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Osprey should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com