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Aug 22 - Aug 24
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Condo Rentals in Osprey

Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1122)
"Everything was perfect with our stay. We will be back soon."
$184 nightly
The price is $204
Aug 14 - Aug 15
Total includes taxes and fees
Captiva Beach Resort
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (427)
"Easy walk or bike ride to beach. Property has plenty of bikes to borrow with locks. Overall just super place that I’ll stay again. "
Venice Beach Villas
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
On the beach

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

8.8 out of 10, Excellent, (22)
"Great view and nice place for a short stay. "
$417 nightly
The price is $464
Aug 18 - Aug 19
Total includes taxes and fees
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Cozy condo in charming Sarasota Siesta key with boat dock
Terrace/patio

Cozy condo in charming Sarasota Siesta key with boat dock

10.0 out of 10, Exceptional, (2)
"Amazing getaway! The location by the water was perfect for relaxing by boat. Cozy and well-equipped, we loved every moment. Highly recommend for a peaceful, scenic retreat."
Cozy condo in charming Sarasota Siesta key with boat dock
Take a Peek at a fabulous unit.
Property grounds

Take a Peek at a fabulous unit.

10.0 out of 10, Exceptional, (122)
"You can not get any closer to the beach than this. The view, the room and our property manager were all amazing. ZERO complaints. Can't wait to go back. "
$527 nightly
The price is $587
Sep 13 - Sep 14
Total includes taxes and fees
Take a Peek at a fabulous unit.
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
Beach nearby, sun loungers, beach towels

DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

10.0 out of 10, Exceptional, (90)
"A beautiful view with amazing comfort in the condo! I can’t wait to come back!❤️😎"
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
On the beach, sun loungers, beach towels

DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!

9.8 out of 10, Exceptional, (58)
"Really nice property. So glad it survived the hurricane. Can’t wait to stay there again. "
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Outdoor dining

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

9.0 out of 10, Wonderful, (17)
"The property was great for our family, loved having a pool and beach access. Super simple especially with a toddler in tow."
$377 nightly
The price is $420
Aug 17 - Aug 18
Total includes taxes and fees
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
On the beach, sun loungers

1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

9.6 out of 10, Exceptional, (157)
"We could not have been happier with this location and its proximity to the beach and the pools. It was also close to great restaurants by locals who proudly serve great food!! "
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
On the beach, sun loungers, beach towels

Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

9.8 out of 10, Exceptional, (259)
"Great location! Beautiful beach! "
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
Prime Beachfront with Views, Views, Views!
Property grounds

Prime Beachfront with Views, Views, Views!

9.6 out of 10, Exceptional, (84)
"The condo was clean, nicely decorated, spacious and very comfortable! It was steps from the beach and pool! The beach is absolutely beautiful! The pool was very nice! We would definitely stay here again! The beds are very comfortable and having two full bathrooms was so nice! We had a great week! "
Prime Beachfront with Views, Views, Views!
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Outdoor pool, a heated pool

Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club

9.8 out of 10, Exceptional, (28)
"Fantastic location!!! Beautiful Beach!! Very clean and updated condo Definitely would stay there again!!! Perfect place to eat, sleep, beach and Repeat!! Loved it!!! "
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Sand in Your Toes . . . Right Out Your Front Door!
Property grounds

Sand in Your Toes . . . Right Out Your Front Door!

9.4 out of 10, Exceptional, (114)
"Clean & comfortable with the beach just steps away!"
Sand in Your Toes . . . Right Out Your Front Door!
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
On the beach

Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC

6.6 out of 10, (7)
"Great location and beach access- pool is awesome! Unit doesn’t face the ocean, but it’s right there! Very low key- place is very clean. WiFi is spotty and would not be good if you are planning to work while staying- that is an island wide issue I believe- No stove, but has everything else a kitchen needs and a grill- we would come back! "
$423 nightly
The price is $471
Aug 18 - Aug 19
Total includes taxes and fees
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Smart TV, books

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (93)
"Lovely unit and the perfect location. Short walk to the beach and easy to get to the shopping/eating areas. "
$369 nightly
The price is $410
Aug 22 - Aug 23
Total includes taxes and fees
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Spacious Penthouse 3bd/3bath, On the Beach, Great Views!
On the beach

Spacious Penthouse 3bd/3bath, On the Beach, Great Views!

10.0 out of 10, Exceptional, (161)
"Absolutely fantastic!! "
Spacious Penthouse 3bd/3bath, On the Beach, Great Views!
On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,
Fridge, microwave, oven, stovetop

On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,

10.0 out of 10, Exceptional, (175)
"Love the condo. I just wish the ocean view was better"
On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
Beach

Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

10.0 out of 10, Exceptional, (113)
"Great place to stay. Accomodations were very good."
$273 nightly
The price is $305
Aug 18 - Aug 19
Total includes taxes and fees
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
Outdoor pool, a heated pool

4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.

10.0 out of 10, Exceptional, (141)
"We love Siesta Dunes! The property is clean and well-maintained. Our unit was beautiful and true to the pictures. The views were outstanding. The owner, Tom, was responsive and helpful with suggestions! We had no issues at all."
4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..
On the beach

Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..

9.6 out of 10, Exceptional, (8)
"The rental was spacious and very clean!!I would definitely stay here again. Place looked exactly like the pictures!! "
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key 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

Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"Muy buenas habitaciones / muy cómodas /servicio excelente solo que les falta un poco de limpieza en la ducha del baño. / La comida no es muy buena si te sales de lo típico . hamburguesas nuggets etc (cumplen con el standar) si pides el sub de langosta, fatal… la atención en todas las áreas es EXCELENTE! "
Luis j 3-night trip
Posted 14 hours ago
Lido Beach Resort