Holiday Homes in Osprey

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Osprey

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 NZ$519
includes taxes & fees
26 Aug - 27 Aug
Charming Florida Beach Home w King Bed Patio
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL
Beach nearby

POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

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 NZ$484
includes taxes & fees
25 Aug - 26 Aug
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL
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 NZ$639
includes taxes & fees
26 Aug - 27 Aug
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 "
RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette
Relaxing 2BR Florida Home Close to Beach
House

Relaxing 2BR Florida Home Close to Beach

2.0 star property
The price is NZ$666
includes taxes & fees
7 Sept - 8 Sept
Relaxing 2BR Florida Home Close to Beach
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."
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 NZ$750
includes taxes & fees
9 Sept - 10 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!!"
Siesta Heron Suites & Villas
Nestled in North Port. Updated 2 Bed / 1 Bath.
Dining

Nestled in North Port. Updated 2 Bed / 1 Bath.

10.0 out of 10, Exceptional, (8)
"We enjoyed our stay! The place was well-decorated, very clean, & overall comfortable. Hosts were very responsive as well!"
Nestled in North Port. Updated 2 Bed / 1 Bath.
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 NZ$466
includes taxes & fees
1 Sept - 2 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 NZ$518
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom house in Englewood with WiFi and AC
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 NZ$422
includes taxes & fees
30 Aug - 31 Aug
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 NZ$588
includes taxes & fees
6 Sept - 7 Sept
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
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 NZ$759
includes taxes & fees
25 Aug - 26 Aug
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
[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 "
[lounge like locals] walk to siesta beach +bikes
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
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 "
Myakka River
Stylish house minutes from the beach
Fridge, microwave, oven, stovetop

Stylish house minutes from the beach

9.6 out of 10, Exceptional, (25)
"Great location and safe neighborhood. Definitely will stay again if available."
Stylish house minutes from the beach
Newly renovated cozy beach house.
Fridge, microwave, oven, stovetop

Newly renovated cozy beach house.

10.0 out of 10, Exceptional, (6)
"We really enjoyed our stay at this cozy beach house. It was exceptionally clean and well stocked. A 5-6 minute drive had us on the beach. Would definitely stay again!"
The price is NZ$575
includes taxes & fees
25 Aug - 26 Aug
Newly renovated cozy beach house.
Peaceful Room 15 Minutes from Downtown or Beach
Terrace/patio

Peaceful Room 15 Minutes from Downtown or Beach

9.6 out of 10, Exceptional, (25)
"Stayed 2 nights so we could attend an Orioles Spring Training game. Very nice facility and very nice hosts! "
The price is NZ$221
includes taxes & fees
31 Aug - 1 Sept
Peaceful Room 15 Minutes from Downtown or Beach
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

Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

10/10 Excellent
"All was very good"
Mohammed 4-night trip
Posted 1 day ago
Embassy Suites by Hilton Sarasota, FL