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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 3679 Vacation Homes in Osprey with updated reviews, rates, and availability.

Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (224)
"Perfect location to walk to beach and town. The Villas and grounds were well maintained. I wouldnt hesitate staying hefe again."
Tropical Villas of Venice Beach
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette
Marina

New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

10.0 out of 10, Exceptional, (4)
"The room which is privately owned is beautiful, exactly like the photos, very well appointed. The location is an older property and who ever redid this room did a great job. The check in and out process was seamless, onsight parking and restaurant/bar/pool/ work out room /boat rental was very convenient. That said, things out of this owner's control but worth noting is you are directly in a flight landing /take off pattern and the planes low and loud. Also the ice machine is right across from...
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette
Siesta Key Island Rentals
Room amenity

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
On the beach, sun loungers, beach towels

SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.8 out of 10, Exceptional, (37)
"Great stay, perfect for what we needed. Beach wedding a few houses down the beach. Location was ideal for us. "
The price is SAR 2,618
SAR 4,847 total
includes taxes & fees
31 Mar - 1 Apr
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Close to Beach Access #7, Short Walk to the Village
Beach nearby, sun loungers, beach towels

Close to Beach Access #7, Short Walk to the Village

9.8 out of 10, Exceptional, (43)
"Perfectly situated to the beach and the village! Well appointed with all necessities niceties."
Close to Beach Access #7, Short Walk to the Village
Private Oasis in Sarasota Florida
Indoor pool

Private Oasis in Sarasota Florida

10.0 out of 10, Exceptional, (26)
"My family and I came down for a weekend stay and the place was perfect for us (2 adults, 3 children ages 3, 9, 13.) We made great use of the backyard pool and lounge area. The location was great for our needs - allowed us to easily get to Siesta Key and up to Ed Smith Stadium for some O's spring training games. The house was exactly as pictured. Check in and out were very easy. "
Private Oasis in Sarasota Florida
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Smart TV, Netflix, streaming services

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

9.2 out of 10, Wonderful, (13)
"Calm neighborhood super quiet enjoyed my stay"
The price is SAR 424
SAR 970 total
includes taxes & fees
22 Apr - 23 Apr
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Private pool House with Fountains & Beach Walkable
Beach nearby

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (170)
"Great place for our short visit for my dad’s 80th birthday! Everyone enjoyed the accommodations and the kids loved the pool. We would have loved to stay longer."
Private pool House with Fountains & Beach Walkable
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches
Terrace/patio

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

7.0 out of 10, Good, (4)
"The home was great, it had everything we needed for our stay. "
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches
Siesta Beach Getaway - Minutes to Beach, Shops, Dining
Interior

Siesta Beach Getaway - Minutes to Beach, Shops, Dining

9.6 out of 10, Exceptional, (10)
"The house was very clean and a perfect location to everything we wanted to do in Sarasota. Lots of shopping, restaurants and beaches nearby. "
Siesta Beach Getaway - Minutes to Beach, Shops, Dining
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!
Outdoor pool, a heated pool

Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!

9.0 out of 10, Wonderful, (57)
"The pool was not very clean. No lights in the BBQ area and pool area. No gas for BBQ , we have to buy it. "
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!
Pineapples House- POOL private SOUTH facing-HOT TUB-close BEACHES- open Mar 6-13
Fridge, microwave, oven, stovetop

Pineapples House- POOL private SOUTH facing-HOT TUB-close BEACHES- open Mar 6-13

10.0 out of 10, Exceptional, (68)
"This was the perfect stay. House was in quiet neighborhood and clean. All you really need is the groceries if you choose to cook. House provided ample kitchen supplies. Nice backyard with pool and setting in shade or sun. Short drives to restaurants, grocery and shopping. Beaches are a quck drive. Communication was wonderful. Enjoyed very much!area. Towels and Linens were nuce."
Pineapples House- POOL private SOUTH facing-HOT TUB-close BEACHES- open Mar 6-13
Private Heated Pool House 6 miles from the Beach
Beach nearby, sun loungers, beach towels

Private Heated Pool House 6 miles from the Beach

10.0 out of 10, Exceptional, (221)
"Nice pool. TV was good; kitchen equipped well for a short stay. Quiet neighborhood."
Private Heated Pool House 6 miles from the Beach
FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.
On the beach, sun loungers, beach towels

FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.

10.0 out of 10, Exceptional, (99)
"A perfect house with stunning views that allow you to see the gulf and the bay, sunrise, and sunset. Updated living spaces with cozy beds and everything you need for a week on the beach. The host is exceptional with excellent communication. You won’t be disappointed. "
FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.
2-bedroom Spacious townhome in Osprey
Fridge, microwave, oven, stovetop

2-bedroom Spacious townhome in Osprey

10.0 out of 10, Exceptional, (3)
"Very nice townhouse with an awsome kitchen, just a short distance off of Highway 41."
2-bedroom Spacious townhome in Osprey
Family Fun House near Siesta Key
Game room

Family Fun House near Siesta Key

10.0 out of 10, Exceptional, (7)
"We stayed here over a soccer tournament weekend with three other families and had the most wonderful, memorable weekend together. Mike, our host, was amazing to work with - very communicative, easy to reach, checked in to make sure we had everything we need. The house was clean, updated, and perfect for us - plenty of space in the main house to enjoy time together and meals, but then also the use of a guest house and mother in law suite so we could spread out. Mike heated the pool for us which...
Family Fun House near Siesta Key
Breezy coastal duplex with private beach access & deck- dog-friendly
Fridge, microwave, oven, stovetop

Breezy coastal duplex with private beach access & deck- dog-friendly

9.0 out of 10, Wonderful, (8)
"We had a lovely time.. needs to be updated. Area rug was very dirty.. could use some small upgrades. Kitchen well equipped."
Breezy coastal duplex with private beach access & deck- dog-friendly
4 Bed pool House by Bay! Lido & Siesta Key Beaches very close
Exterior

4 Bed pool House by Bay! Lido & Siesta Key Beaches very close

9.8 out of 10, Exceptional, (101)
"We really enjoyed the property location, which allowed for nightly walks through a charming neighborhood to see the sunset over the beach. It is also convenient to the main thoroughfare and key attractions. Large backyard, plus room to spread out inside the house. Wonderful stay! "
4 Bed pool House by Bay! Lido & Siesta Key Beaches very close
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village
Fridge, microwave, oven, stovetop

Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

9.6 out of 10, Exceptional, (8)
"Unit was a bit dated, but you couldn't beat the location. Seconds from the beach and minutes from the village via walk. "
The price is SAR 1,652
SAR 3,846 total
includes taxes & fees
15 Apr - 16 Apr
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village
SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!
Beach nearby

SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!

9.8 out of 10, Exceptional, (27)
"Considering all of the local hurricane damage, the upstairs stay was very nicely cleaned up. The balcony neeeds some repair but no concerns about safety. "
SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!
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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Other property types in Osprey

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4605)
"This place was absolutely perfect for what we were looking for. Rooms were clean and completely updated and the beds were so comfortable. Walking distance to the beach and a pool on site. We learned they were hit by 2 hurricanes so there was some construction going on. We didn’t realize this prior to arriving but it was just a minor inconvenience really. The staff were friendly and so helpful, can’t wait to return. "
The price is SAR 971
SAR 1,182 total
includes taxes & fees
30 Mar - 31 Mar
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2105)
"Great little hotel close to the beach, but not so close as to be over-priced. Easy 15 min walk to a public beach access in one direction and 10 min walk to several restaurants/groceries in the other direction. Very clean and updated room with a full size refrigerator and small kitchen. The pool was the best part. Comfortable chairs and never crowded."
The price is SAR 715
SAR 807 total
includes taxes & fees
3 Apr - 4 Apr
Hibiscus Suites - Gateway to Siesta Key
The Ringling Beach House
Aerial view

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (295)
"We very much enjoyed our stay. Our room was clean and ready for us early. Nancy, the manager, couldn’t have been nicer. This is a no-frills place—but the location can’t be beat! You walk across the street to the beach, and the lively shopping area with restaurants and fun is so close. It’s a quick walk, or you can take the free trolleys/busses. The outdoor area with a nice pool was so relaxing. We used it often. We would stay again. We had 3 teens with us, and they had a blast. We all felt safe....
The Ringling Beach House
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.