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City Breaks and Short breaks in Osprey and nearby – Holiday Villas

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All 426 Rentals in the Osprey Area
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From
£86
Per Night
Osprey
3 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
17 photos Details
Reviews (1) Make Enquiry
5 of 5 stars Reviewed 26 June 2014
Me and 5 other people stayed at this beautiful house for one week. The house is located in a quiet and beautiful neighborhood. We were only a few minutes from Siesta Key Beach...
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From
£420
Per Week
Osprey
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
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From
£30
Per Night
Osprey
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
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Also consider
Ebb Tide Tropical Villa,Pool,Wifi, Great Value!
1 Bedroom, sleeps 4
£56 - £66 / night
WALK TO BEACH RENTAL
3 Bedrooms, sleeps 6
£60 / night
Luxury home on the Island of Venice
3 Bedrooms, sleeps 5
£200 / night
The Siesta Calm Upstairs: Location,View, Steps from the Beach
2 Bedrooms, sleeps 5
£85 - £148 / night
From
£1,200
Per Month
Osprey
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details
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The following rentals are within 15 kilometres of Osprey, Florida.

From
£66
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
17 photos Details
Reviews (1) Make Enquiry
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4 of 5 stars Reviewed 11 August 2014
The villa totally met our needs: beaches near by (10-minute walk from Crescent Beach and 5-minute drive to Siesta Key Beach), great pool in a relax community, clean house with...
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From
£81
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 6 August 2014
My Husband and I have stayed in this Condo several times. We come back year after year because it is a beautiful condo, clean, comfortable, and the location is perfect. It's...
5 of 5 stars Reviewed 1 August 2014
Working with the owner to arrange our week long stay was very easy! Check in a breeze! The unit was just as pictured and clean! The proximity to the Gulf unsurpassed......steps...
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From
£60
Per Night
Nokomis
1 Bedroom, 1 Bathroom, Sleeps 2
18 photos Details
Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 March 2013
We actually did not stay in this unit ( although we did go into it), we stayed at the 2 bedroom unit next door. The decor was old Florida with a touch of Hawaii, very chic yet...
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From
£550
Per Week
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
12 photos Details
Reviews (1) Make Enquiry
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5 of 5 stars Reviewed 11 May 2014
My husband and I stayed here with our five children. This place was perfect for us. It was clean and comfortable. I was surprised to find every single thing I needed in the...
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From
£480
Per Week
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
20 photos Details
Reviews (7) Make Enquiry
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5 of 5 stars Reviewed 7 August 2014
We stayed for two weeks and did not have anything to complain about. The beach was a short walk and the cabana had everything you needed to spend the day including seats and...
5 of 5 stars Reviewed 15 July 2013
We have just recently spent two weeks of our three week vacation at the Baytree Club on Siesta Key. The condo, location and Siesta Key were just perfect. The condo's position is...
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From
£90
Per Night
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
40 photos Details
Reviews (5) Make Enquiry
From
£47
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
12 photos Details
Reviews (11) Make Enquiry
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4 of 5 stars Reviewed 8 August 2014
We had very nice stay at Michel. Before our arrival we got all the instructions - where to pick up the keys, password to internet, etc so we didn't have any obstacles upon our...
5 of 5 stars Reviewed 27 April 2014
We stayed here for 2 weeks in April 2014. We really enjoyed our holiday. The condo was very clean and spacious. There was WiFi, cable TV, and everything you needed for the beach...
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From
£90
Per Night
Siesta Key
4 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
26 photos Details
Reviews (1) Make Enquiry
From
£1,860
Per Week
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
23 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 26 March 2014
We had a wonderful relaxing week in this beautifully renovated condo. We loved the panoramic views of the gulf, the proximity to the village and the easy access to the beach...
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From
£60
Per Night
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
14 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 28 May 2014
We had an awesome time at this vacation rental. Elvis, the owner, was very accommodating and catered to our specific needs. The condo was very clean and a nice size, with a...
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From
£1,497
Per Month
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
10 photos Details
Reviews (1) Make Enquiry
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5 of 5 stars Reviewed 28 January 2014
This condo provides everything a family needs for a delightful vacation. The kitchen, bathrooms and bedrooms are as fully equipped as those of a regular home; the lanai and the...
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From
£38
Per Night
Venice
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
20 photos Details
Reviews (1) Make Enquiry
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4 of 5 stars Reviewed 10 August 2014
A nice, small condo at a very affordable price. Very good for one or two people who come to relax at the beach and not stay indoors all day. Interior is a little busy but there is...
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From
£60
Per Night
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
9 photos Details
Reviews (2) Make Enquiry
From
£60
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
32 photos Details
Reviews (2) Make Enquiry
From
£75
Per Night
Nokomis
3 Bedrooms, 1 Bathroom, Sleeps 5
Booking
8 photos Details
Reviews (2) Make Enquiry
5 of 5 stars Reviewed 30 December 2013
We stayed here in November over the Thanksgiving holiday into December. The house is very pretty and immaculately clean and in a great spot for everything. The owners were lovely...
5 of 5 stars Reviewed 31 August 2013
Great place, relaxing & private, very big well maintained lot, all amenities incl, hosts very thoughtful and helpful, 30 min walk/ 5min drive to public beach
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From
£34
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
11 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 23 July 2014
We had the best time ever. Nice being able to wLk to village. Sunsets are beautiful. Dolphin hanging out at the pier Beaches are near. The pool is next door. Condo is...
4 of 5 stars Reviewed 13 July 2014
I had a wonderful experience at the condo. The only things I did not like was the limit on the time that children can be in the pool. The Children could only be in the pool from...
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From
£171
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
24 photos Details
Reviews (1) Make Enquiry
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5 of 5 stars Reviewed 3 August 2014
We really enjoyed staying at this beach house; I couldn't imagine a better location. Right on the beach, and just a couple of minutes walk to the Siesta Key village. The...
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From
£870
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 19 May 2014
My husband, 2 kids (7&6), and myself have stayed at this condo several times and we highly recommend it to anyone considering a beach vacation in Florida. Bottom line... This...
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From
£69
Per Night
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
14 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 31 May 2014
Martin & Victoria, My boyfriend and I stayed at your unit for one week after having read about beautiful Siesta Key! Well, Siesta Key was definitely a pleasure, the beach was...
5 of 5 stars Reviewed 27 January 2014
Everything they report that comes with the home is there! And 2 min. Walk to the private beach entrance was great! The bathroom was a little small & with 4 people a little...
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From
£42
Per Night
Nokomis
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
11 photos Details
Reviews (1) Make Enquiry
From
£52
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
14 photos Details
Reviews (3) Make Enquiry
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5 of 5 stars Reviewed 22 June 2014
This place is fantastic you have everything you need, beach chairs, beach toys inner tubes, beach is a short walk across the street white powder sand not too crowded, if you want...
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From
£795
Per Week
Venice
4 Bedrooms, 4 Bathrooms, Sleeps 8
23 photos Details
Reviews (3) Make Enquiry
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5 of 5 stars Reviewed 10 May 2013
The house is on a superb gated community with a club house, swimming pool and amenities. There was acres of room, very well furnished and immaculately presented. Located off the...
5 of 5 stars Reviewed 6 January 2013
We chose this villa after a couple of conversations with the owner Doreen and decided it was just what we were looking for. After holidaying in Orlando two years earlier and...
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From
£105
Per Night
Nokomis
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
22 photos Details
Reviews (9) Make Enquiry
4 of 5 stars Reviewed 20 April 2012
If you want to see water from every room,if you want to watch the pelicans nap or if you want to relax next to the water this is the place. This home is situated in a quiet area...
3 of 5 stars Reviewed 6 April 2012
The house was adequate for our needs as we just slept and showered there and went to the nearby public beach every day. We never got in the pool -- it seemed nice enough and...
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From
£39
Per Night
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
6 photos Details
Reviews (1) Make Enquiry
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5 of 5 stars Reviewed 6 October 2013
A really nice vacation home in Venice Florida. Ideally situated with easy access to all Local amenities, beaches, shops, eateries and road networks. The house is well fitted out...
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From
£40
Per Night
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
25 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 18 May 2014
This was a perfect place for my sisters and myself. Total of six women. It was clean and in a quite neighborhood but close to some very good dinning and attractions. Siesta beach...
4 of 5 stars Reviewed 30 June 2013
Comfortable, convenient, affordable. Seems like a great value for the area. Enjoyed my week and would absolutely stay again. Didn’t realize how handy this location would be, it...
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From
£58
Per Night
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
16 photos Details
Reviews (7) Make Enquiry
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5 of 5 stars Reviewed 18 July 2014
great place, clean and excellent location. dereck was extremely helpful. will stay again. the room is a one bedroom so a little limited in space but i enjoyed it. the outdoor area...
3 of 5 stars Reviewed 13 July 2014
The room was nice, clean, had everything you needed. The beach was farther than 150 yards. Room was quiet until a couple with kids came, you could hear everything. If you don't...
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From
£99
Per Night
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
44 photos Details
Reviews (1) Make Enquiry
From
£78
Per Night
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
18 photos Details
Reviews (17) Make Enquiry
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5 of 5 stars Reviewed 14 April 2014
Perfect condo for a family of five on Seista Key with everything you need already there. Location was peacefully secluded but the bikes provided made the village and beach easily...
5 of 5 stars Reviewed 13 January 2014
My wife and I had a very pleasant stay here. The property is very well maintained and very convenient to everything including the beaches and Siesta Key Village. We especially...
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From
£90
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
17 photos Details
Reviews (3) Make Enquiry
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5 of 5 stars Reviewed 15 June 2014
We really enjoyed our stay at Sandy Toes , the location was perfect , just a walk to one if the best beaches in the world. Just a short walk to restaurants and shopping in the...
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From
£73
Per Night
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
26 photos Details
Reviews (20) Make Enquiry
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5 of 5 stars Reviewed 25 June 2014
Ebb tide villa #3 has the feel of home when we come to siesta key Sue is so nice to us when we arrive and when we depart. The place is spotless we have the best time on the...
5 of 5 stars Reviewed 7 October 2012
We just came home from our trip to Siesta Key. What a beautiful place. Ebb Tide was so quiet, relaxing and private. If you are looking to get away from stress then come here and...
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From
£60
Per Night
Nokomis
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
26 photos Details
Reviews (1) Make Enquiry
5 of 5 stars Reviewed 8 October 2010
This is really a charming cottage and I definitely felt like I was in "Old Florida" when I stayed there. The location is very quiet and unassuming and only minutes from Venice...
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From
£96
Per Night
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
14 photos Details
Reviews (3) Make Enquiry
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5 of 5 stars Reviewed 15 August 2014
My family and I stayed at Fishermans Cove unit 102 from August 1-13. We found the pictures and description of the condo online to be accurate. The condo included many amenities...
5 of 5 stars Reviewed 25 June 2014
My wife, grown son and I spent a week in this lovely condo directly on the beach on Siesta Key. The condo is a really nice 2 bedroom, 2 bath unit on the first floor so that you...
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From
£105
Per Night
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
21 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 4 August 2014
Great vacation rental. Stayed with my spouse and three kids. Plenty of space and the apartment has everything you will need for a day at the beach (cooler, umbrella, chairs etc...
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From
£73
Per Night
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
22 photos Details
Reviews (29) Make Enquiry
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5 of 5 stars Reviewed 27 June 2014
We greatly enjoyed our stay at Ebb Tide. Very cute villa with a beautiful garden patio. Villa # 1 was quiet even though it was next to the laundry room and the road - never...
5 of 5 stars Reviewed 18 June 2014
We stayed in Villa # 1 for a weekend getaway. This was the first time we have been to Siesta Key. Sue had everything we needed, bed was so comfortable, and place was spotless. The...
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From
£105
Per Night
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
33 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 16 July 2013
The house was super clean and with everything we needed to spend a week. It is fully equipped with all the appliances and more...We had plenty of room for 4 adults and a child...
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From
£130
Per Night
Siesta Key
3 Bedrooms, 3 Bathrooms, Sleeps 10
42 photos Details
Reviews (22) Make Enquiry
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5 of 5 stars Reviewed 16 August 2014
One of the things that I loved about this home was how clean it was. When you travel with your family, you want it to be fun and relaxing, but you also want your family to stay...
5 of 5 stars Reviewed 27 May 2014
My family & I stayed here for a week-5 adults & 5 children..it was wonderful! Be careful of the stairs I think they're a little higher than most & 3 of us tripped. So once we got...
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Suitability

  • Wheelchair access (70)
  • Elder access (179)
  • Suitable for children (224)
  • Pet friendly (90)
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Amenities

  • Air Conditioning (350)
  • Internet (334)
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