Holiday Homes in Osprey

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Holiday Homes in Osprey

Our top choices for Osprey holiday homes

Charming Florida Beach Home w King Bed Patio
House

Charming Florida Beach Home w King Bed Patio

2.0 star property
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
The price is AU$514
includes taxes & fees
16 Sept - 17 Sept
Charming Florida Beach Home w King Bed Patio
Relaxing 2BR Florida Home Close to Beach
House

Relaxing 2BR Florida Home Close to Beach

2.0 star property
The price is AU$569
includes taxes & fees
3 Sept - 4 Sept
Relaxing 2BR Florida Home Close to Beach
2BR Oasis with a Cozy Lanai 5 Min to Nokomis Beach
Beach

2BR Oasis with a Cozy Lanai 5 Min to Nokomis Beach

8.0 out of 10, Very good, (2)
"Everything was lovely, just as described. The only problem was the ant problem in the kitchen. "
The price is AU$625
includes taxes & fees
10 Sept - 11 Sept
2BR Oasis with a Cozy Lanai 5 Min to Nokomis Beach
RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette
Property grounds

RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette

9.6 out of 10, Exceptional, (35)
"The unit is very nice with everything for a great comfortable stay.. the water view and onsite restaurants are a bonus "
The price is AU$346
includes taxes & fees
9 Sept - 10 Sept
RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette
POOL VIEW Walk to beach King bed Pool Daily Rentals
Beach nearby, sun-loungers, beach towels

POOL VIEW Walk to beach King bed Pool Daily Rentals

9.6 out of 10, Exceptional, (32)
"We enjoyed our stay. Close to the beach. enjoyed the pool.Kitchen was perfect we were able to make breakfast and dinner."
The price is AU$521
includes taxes & fees
1 Sept - 2 Sept
POOL VIEW Walk to beach King bed Pool Daily Rentals
Cozy condotel with King Bed, WiFi, great pool, fitness room and much more!
Marina

Cozy condotel with King Bed, WiFi, great pool, fitness room and much more!

10.0 out of 10, Exceptional, (2)
"This unit was well stocked and very nicely decorated. The bed was comfy! We needed to be close to our clinic and this suited our needs well. It was great going to the pool and walking along the marina. The restaurant/tiki bar right on site was fun and the food was good. It was so nice not having to drive anywhere for dinner after a long day! We would definitely stay in this unit again. The owners were super quick to respond and helpful."
The price is AU$313
includes taxes & fees
10 Sept - 11 Sept
Cozy condotel with King Bed, WiFi, great pool, fitness room and much more!
2BR Florida Home Near the Shore!
Beach nearby

2BR Florida Home Near the Shore!

6.8 out of 10, (3)
"Had an odor. Property by major roadway. Other than than it was good"
The price is AU$673
includes taxes & fees
3 Sept - 4 Sept
2BR Florida Home Near the Shore!
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
The price is AU$876
includes taxes & fees
31 Aug - 1 Sept
Siesta Heron Suites & Villas
New Two story Cozy House Near Warm Mineral Springs
Fridge, microwave, oven, stovetop

New Two story Cozy House Near Warm Mineral Springs

10.0 out of 10, Exceptional, (15)
"Had an awesome with friends and family and will stay again if we’re in the area."
New Two story Cozy House Near Warm Mineral Springs
Charming home near Anna Maria Island with Jacuzzi
Smart TV, stereo

Charming home near Anna Maria Island with Jacuzzi

2.0 star property
10.0 out of 10, Exceptional, (14)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
The price is AU$424
includes taxes & fees
9 Sept - 10 Sept
Charming home near Anna Maria Island with Jacuzzi
Charming 2-bedroom house in Englewood with WiFi and AC
Beach

Charming 2-bedroom house in Englewood with WiFi and AC

The price is AU$473
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom house in Englewood with WiFi and AC
Relaxation Awaits: Luxurious Vacation Home with Heated Pool near Mineral Springs
A heated pool

Relaxation Awaits: Luxurious Vacation Home with Heated Pool near Mineral Springs

2.0 star property
10.0 out of 10, Exceptional, (6)
"We needed a place to shelter from the hurricane for a few days. This home is beautiful, comfortable and has everything we needed. Communication with the owner was extremely easy. Would definitely stay again. "
The price is AU$890
includes taxes & fees
25 Sept - 26 Sept
Relaxation Awaits: Luxurious Vacation Home with Heated Pool near Mineral Springs
2 Bedroom in Olde Englewood minutes from the beach with privacy fenced yard.
Sun-loungers, beach towels

2 Bedroom in Olde Englewood minutes from the beach with privacy fenced yard.

9.8 out of 10, Exceptional, (25)
"Very quaint home, it was perfect for us to get away for a birthday weekend and enjoy the beach!"
The price is AU$390
includes taxes & fees
10 Sept - 11 Sept
2 Bedroom in Olde Englewood minutes from the beach with privacy fenced yard.
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Property grounds

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

2.0 star property
10.0 out of 10, Exceptional, (18)
"Great stay! Nice place and location!"
The price is AU$532
includes taxes & fees
1 Sept - 2 Sept
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
The price is AU$493
includes taxes & fees
3 Sept - 4 Sept
Siesta Key Island Rentals
[lounge like locals] walk to siesta beach +bikes
Fridge, microwave, oven, stovetop

[lounge like locals] walk to siesta beach +bikes

9.8 out of 10, Exceptional, (23)
"Lovely stay at Siesta Key! Minute walk to beaches and restaurants. Very spacious and clean! Highly recommended "
The price is AU$487
includes taxes & fees
29 Aug - 30 Aug
[lounge like locals] walk to siesta beach +bikes
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Beach

Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

9.6 out of 10, Exceptional, (35)
"Looking forward to staying there again."
The price is AU$692
includes taxes & fees
29 Aug - 30 Aug
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Myakka River
Fridge, microwave, oven, stovetop

Myakka River

9.8 out of 10, Exceptional, (18)
"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 "
The price is AU$687
includes taxes & fees
29 Aug - 30 Aug
Myakka River
Modern 2 Bedroom Farmhouse
Private kitchen

Modern 2 Bedroom Farmhouse

9.2 out of 10, Wonderful, (7)
"Would highly recommend for a one or two night stay"
Modern 2 Bedroom Farmhouse
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home
House, 3 Bedrooms | Property grounds

Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home

3.0 star property
The price is AU$668
includes taxes & fees
10 Sept - 11 Sept
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home
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

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
1,398
Accommodation
3947 Holiday Homes
Lowest Price
AU$493
Highest Price
AU$876

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