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

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (226)
"Amazing 3 day get away. The best place to stay in Venice! "
Tropical Villas of Venice Beach

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

10.0 out of 10, Exceptional, (5)
"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...
The price is SAR 259
SAR 580 total
includes taxes & fees
21 Apr - 22 Apr
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

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

9.6 out of 10, Exceptional, (42)
"Beautiful place right on the beach in a great location. We enjoyed our stay very much"
The price is SAR 2,994
SAR 5,298 total
includes taxes & fees
15 May - 16 May
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

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

9.8 out of 10, Exceptional, (45)
"The property was very clean and the check in process was incredibly easy. Just a couple minor issues like some wall outlets not working and the shower/bathtub not draining very well. They provided us with beach towels, beach chairs and umbrellas. Close to the beach, shops and dining. Would recommend for couples and families. "
The price is SAR 747
SAR 2,009 total
includes taxes & fees
2 May - 3 May
Close to Beach Access #7, Short Walk to the Village

Private Oasis in Sarasota Florida

10.0 out of 10, Exceptional, (30)
"This sweet home has an amazing backyard oasis. The pool house is very cool also and a great place to do yoga or watch a movie. The location is great—a very walkable neighborhood and an easy walk to shops and dining. Would definitely recommend!"
Private Oasis in Sarasota Florida

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

9.2 out of 10, Wonderful, (13)
"Great location! Clean, easy to find and perfect amount of room. "
The price is SAR 296
SAR 826 total
includes taxes & fees
21 Apr - 22 Apr
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (172)
"Great location. Beach couple blocks away-walkable which is a plus for us. During spring break traffic is heavy so we can walk to beach or historic downtown or to local restaurants.Rented e-bikes for a few days and explored."
Private pool House with Fountains & Beach Walkable

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

6.8 out of 10, (6)
"Property was clean, larger than expected and host was very accommodating and responsive. "
The price is SAR 657
SAR 1,841 total
includes taxes & fees
13 May - 14 May
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

Siesta Beach Getaway - Minutes to Beach, Shops, Dining

9.6 out of 10, Exceptional, (11)
"The house was lovely and was close to many amenities and several beaches. The neighborhood was very quiet. "
Siesta Beach Getaway - Minutes to Beach, Shops, Dining

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 to BEACHES-walkable

10.0 out of 10, Exceptional, (70)
"We traveled to Sarasota for Spring Break 2025. The house, pool, and property was very clean. The kitchen and bathrooms were well stocked with everything you would need for a week long stay. We appreciated the beach chairs, cooler, & pool/sand toys. Nicely located between Siesta Key and Lido Beach. Both have beautiful beaches and some great restaurants. Christine was a great hostess checking several times making sure everything was ok. We had a family of four, including 2 teenagers. The...
Pineapples House - POOL private SOUTH facing - HOT TUB-close to BEACHES-walkable

Private Heated Pool House 6 miles from the Beach

9.8 out of 10, Exceptional, (222)
"The property was very clean and centrally located. It was smaller than we expected but was sufficient for the two of us. The heated pool was very nice for this time of year (April). I would recommend that the host provide fans since there was not any ceiling fans in the bedrooms. A lot of folks need a fan to sleep."
Private Heated Pool House 6 miles from the Beach

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

10.0 out of 10, Exceptional, (100)
"This house was perfect!! Beautiful inside and out with a short walk to the beach. We enjoyed fishing from the beach, the Sand Bar for lunch and local fish from the market. House was well stocked with supplies for the beach and host was terrific with excellent communication. We have been to the area several times and this was by far and away our best trip. Just an amazing house and we cannot recommend it enough!!!!"
FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.

2-bedroom Spacious townhome in Osprey

10.0 out of 10, Exceptional, (6)
"property was immaculate, Host was very helpful, an excellent shower, beds very comfortable, location quiet and secluded.will stay again when in Osprey."
2-bedroom Spacious townhome in Osprey

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

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

9.8 out of 10, Exceptional, (104)
"Good location to be close to airport and short drive to beaches. There’s lots to do in the area! We were a little frustrated when we arrived the pool was low on water so the pump had not been running. Had to have pool people and electricians there and didn’t get fixed until our last day. Pool guys did not do anything to clean besides dump chemicals so my husband was cleaning it and filling it with a garden hose so our kids could at least float in it. "
4 Bed pool House by Bay! Lido & Siesta Key Beaches very close

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 2,153
SAR 4,483 total
includes taxes & fees
7 May - 8 May
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

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

9.6 out of 10, Exceptional, (29)
"Clean and very close to village."
The price is SAR 1,118
SAR 2,397 total
includes taxes & fees
28 Apr - 29 Apr
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

Huge Pool, Close to Beaches, Restaurants, Shopping & More!

9.6 out of 10, Exceptional, (22)
"What a wonderful place to relax! Will definitely recommend to family and friends and even come back to stay!"
Huge Pool, Close to Beaches, Restaurants, Shopping & More!

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4628)
"Nice place and clean! Staff was very friendly and helpful. "
The price is SAR 522
SAR 674 total
includes taxes & fees
21 Apr - 22 Apr
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2113)
"Location is great..Crescent Beach within a reasonable walking distance. The suite was clean and comfortable. The staff were very helpful. The pool is a nice feature. Extra amenities like beach towels, chairs , umbrellas, grills to cook on were nice. Only negative was that the street is busy so the traffic is a little loud by the pool or if you are sitting outside your room. Inside it is not a bother.This is my second time here... I would come back."
The price is SAR 619
SAR 699 total
includes taxes & fees
4 May - 5 May
Hibiscus Suites - Gateway to Siesta Key
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.