Holiday Homes in Osprey

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Featured Holiday Homes in Osprey and around

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (48)
"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. "
Siesta Key Island Rentals

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.6 out of 10, Exceptional, (52)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
The price is €795
includes taxes & fees
30 Sept - 1 Oct
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

9.8 out of 10, Exceptional, (111)
"Great location and close to beach"
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (137)
"The home was cozy. Best feature- so close to the beach! "
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Charming 2-bedroom house in lovely Sarasota with yard.

10.0 out of 10, Exceptional, (1)
"Easy to check in, clean and comfortable "
The price is €172
includes taxes & fees
30 Sept - 1 Oct
Charming 2-bedroom house in lovely Sarasota with yard.

Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

10.0 out of 10, Exceptional, (122)
"I booked this property for a girl’s trip and did was WONDERFUL! It was nice, clean, and very convenient to the beach. The host was very friendly and she responded quickly to my messages. I will definitely stay here again when we return to the area. "
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

Private Home Directly on Siesta Key Beach!

9.8 out of 10, Exceptional, (6)
Private Home Directly on Siesta Key Beach!

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (24)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (66)
"Very comfortable and perfect location to the airport! "
The price is €172
includes taxes & fees
30 Sept - 1 Oct
Casa Azul 2Bed/1Bath

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

9.6 out of 10, Exceptional, (5)
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

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

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

7.8 out of 10, Good, (21)
"Great spit in Venice to bring the dogs and enjoy some early summer vacations "
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

4-Bedroom Pool Home Convenient To Beaches

9.8 out of 10, Exceptional, (143)
"This is our second time at this vacation home and we absolutely love everything about it! From the location, the pool, the house, and the area itself is so quiet as well as peaceful. Not far from beaches. Also, that it is pet friendly which is a plus! Highly recommend this place. "
4-Bedroom Pool Home Convenient To Beaches

All Oar Nothing | 4800 sqft. Luxury Home! Walk to Lido Beach, Bike to St Armand Circle

9.6 out of 10, Exceptional, (9)
"Beautiful home, lots of space, awesome location!! "
All Oar Nothing | 4800 sqft. Luxury Home! Walk to Lido Beach, Bike to St Armand Circle

Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

9.0 out of 10, Wonderful, (33)
"No issues.. we enjoyed our stay. Nice and quiet. "
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

10.0 out of 10, Exceptional, (41)
"We stayed a week with a family of 11.We absolutely loved it something for everyone. Close to anything you need within walking distance. Easy in and easy out. Would stay again. Lots of memories.Owner very responsive to anything you might need."
Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3

9.8 out of 10, Exceptional, (102)
"Perfect location for beach access and a short walk to the village. "
Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3

Newly renovated TH in Siesta Key FL - #1 beach in US

6.0 out of 10, (1)
"Property was very dated. Noisy street location for the guest bedroom; master was fine. Property is located in a good condo complex. Private beach not crowded at all. Set in a very lush tropical garden. Not what we expected but adequate for our visit. If the new owner is going to continue to rent he needs to perform some major renovations/updates."
Newly renovated TH in Siesta Key FL - #1 beach in US
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
1,151
Accommodation
3924 Holiday Homes
Lowest Price
€172
Highest Price
€795

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