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Siesta Key Holidays & City Breaks - Holiday Lettings

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61 properties suitable for city breaks and holidays

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Siesta Key holiday apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £184 / night

£1,284 - £2,276 / week

1 / 59

Siesta Key holiday condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 5

“Oceanfront views right on the beach in the low key area of Turtle Beach” My family consists of my wife, 14 and 11 year olds, and me. This condo has a King master bedroom with a Gulf water view, and a bedroom with bunk beds. Both bedrooms have their own shower and bathroom. The condo is on the low-key more residential side of Siesta Key called Turtle Beach. It is still very near supplies, restaurants, pubs, markets, post office, grocery and lunch spots. It's just that Turtle Beach is more secluded and less "Animal House" than downtown Siesta Beach. If you want to relax, fish, lay on the beach, read a book on the patio at sunrise or sunset, and watch the sun set over the Gulf every night in your windows, then this is your place. There is a nice sized living room with couch, chairs, and flat screen TV. It has a full operational kitchen with full refrigerator and all kitchen gadgets and supplies. We made two very nice meals there, lots of breakfasts', and had friends over several times for cocktails and beach time. The condo has it's own numbered parking spot, and a marina slip for each unit with a boat ramp very nearby. You can fish for snook in the marina, or the beach is great too for fishing. The condo is near the stairs, elevator and laundry but that did not make it loud, just convenient. There is a freshwater shower and a walkway over the dune right by the condo. The common pool is small but clean and close if you want to go beach-pool-nap mode. We chartered Siesta Key Fishing Charters and caught almost 100 fish offshore, 10 huge keeper Red Grouper that we ate in the condo, froze and took home, gave away and traded for other cool stuff. We also really enjoyed eating at Big Water Seafood Market, they will clean and cook your fish, or sell you some, or feed you at their restaurant. Both of those companies can also be found highly rated on TripAdvisor. That's how I found all three....and I couldn't be happier. It was a great vacation at a chill place decorated "beachy style", on a relaxed beach near nice convenient stops, all the while having Siesta Village and Siesta Key Beach just down the road. Siesta Village is awesome and less crowded on weekdays. We had no problem parking even with the July 4th weekend and the offshore powerboat racing both that week. That being said this is a rental condo, and they are not perfect, because they are used and loved. I miss it. We will go back. And, the owners are super good at communicating, troubleshooting, returning security deposits, and all the other things we would hope work well after a great relaxing week. Be careful shopping, there are a lot of condos that say waterfront that aren't oceanfront. and lots of condos aren't really on the ocean although you are made to believe they are, but this one really is. Big Gulf of Mexico views in your face for a week. Big sunsets. Big sunburns. Big bellies full of super fresh fish. Big smiles from your family and friends. I say, book it and dare to be called Vacation Hero....

from £350 / night

£2,448 / week

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Holiday townhouse in Siesta Key

Siesta Key townhouse

2 bedrooms • 4 bathrooms • sleeps 6

from £322 / night

£2,254 / week

1 / 38

Apartment rental in Siesta Key with golf nearby

Siesta Key apartment

2 bedrooms • 1 bathroom • sleeps 6

from £163 / night

£1,137 - £1,739 / week

1 / 20

Townhouse rental in Siesta Key

Siesta Key townhouse

3 bedrooms • 3 bathrooms • sleeps 8

from £352 / night

£2,465 / week

1 / 35

Villa rental in Siesta Key

Siesta Key villa

3 bedrooms • 3 bathrooms • sleeps 8

“I'll be back!” We crave sea, sand, and sun, so a couple of years ago we drove from Toronto, Canada all the way south to Key West and back staying in several locations on the east and then west coast of Florida and we picked Siesta Keys as our family vacation spot. First year we booked online and then on location went to check out local rental properties and prices. This townhouse was #1. It's beautiful, fresh as if you're the first to live in it, neatly decorated and very close to the beach (we just walked barefoot and in our swimwear for about 100m - and there you are at the water), best in location and price! We spent three weeks in 2011 and came back again for the august 2012. It's truly a pleasure to deal with people like Tim&Viv;! I'm very grateful for their informative responses to our inquiries about the place and amenities around and kind attention to details in preparing the house for our stay. As soon as we entered the spacious sunlit living room and I saw the basket with welcome gifts on the table I knew it was time to relax and enjoy my vacation. It switched me into a different mood right away - peaceful, joyful and relaxed. Coming from a big city with its daily hustle-bustle we really appreciate the difference in atmosphere and pace here it doesn't take days or weeks to "decompress". Tim&Viv; knew how to make it very easy, relaxing, and comfortable. Our kids were very happy to find bikes and swimming gear in the garage not to mention to have one TV in each room so remote control wars were prevented. We try to buy organic so it's very convenient to have an Earth Origins Market 3min away. Also there's a Publix and many restaurants in the area. For art lovers there's a great art gallery in Sarasota: Ringling Museum of art - surprisingly rich collection of works by the Old Masters. A visit here is a must! Sunsets here are so spectacular that their grandeur can never be captured by a camera. I hope we'll come back again and again to the warmth and hospitality of this house.

from £332 / night

£2,319 / week

1 / 52

Siesta Key holiday apartment rental

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £215 / night

£1,503 / week

1 / 24

Holiday apartment in Siesta Key

Siesta Key apartment

1 bedroom • 1 bathroom • sleeps 4

from £155 / night

£1,082 / week

1 / 15

Holiday apartment in Siesta Key

Siesta Key apartment

3 bedrooms • 3 bathrooms • sleeps 6

“Smith Family Wedding” I just want to thank Virginia for all her wonderful touches she did for the "Smith Family Wedding Weekend"...she had Big White Bows on the doors of the rooms we rented for the family. Inside the suites she had bride and groom cut-outs with wine glasses decorated with wedding rings...We had such a great time as a family...the pictures on her web site are a great representation of the suites and grounds. I just can't say enough about how wonderful this place was...she thinks of everything...books... Games...toy chest for kids...every thing you would need to live and play...We had three units, 662, 5610 and the Honeymoon Suite...and to the guy who wrote on aug13,2011 (JS Tampa FL) that it was shabby was nuts...I hope our family can do this again...It is a must for family fun...a home away from home!!!

from £257 / night

£1,798 / week

1 / 31

Holiday condo in Siesta Key

Siesta Key condo

1 bedroom • 1 bathroom • sleeps 3

from £81 / night

£561 / week

1 / 40

Holiday home with swimming pool in Siesta Key

Siesta Key house

4 bedrooms • 4 bathrooms • sleeps 12

from £279 / night

£2,147 / week

1 / 23

Great rentals within 20 miles that match your search

Home rental in Bradenton with golf nearby

Bradenton house

4 bedrooms • 2 bathrooms • sleeps 8

from £12 / night

£695 - £1,699 / week

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Bradenton Beach holiday home rental

Bradenton Beach house

3 bedrooms • 3 bathrooms • sleeps 6

from £172 / night

£1,203 - £2,061 / week

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Holiday studio in Longboat Key

Longboat Key studio

Studio • 1 bathroom • sleeps 2

from £104 / night

£728 - £1,082 / week

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Home rental in Venice

Venice house

3 bedrooms • 2 bathrooms • sleeps 5

from £95 / night

£644 - £687 / week

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Holiday caravan/mobile home in Bradenton

Bradenton caravan/mobile home

1 bedroom • 1 bathroom • sleeps 2

from £43 / night

£301 / week

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Holiday apartment with golf nearby in Bradenton

Bradenton apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £108 / night

£752 / week

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Holiday apartment with golf nearby in Bradenton

Bradenton apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £101 / night

£702 / week

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Holiday private room in Sarasota

Sarasota private room

1 bedroom • 1 bathroom • sleeps 2

from £137 / night

£956 / week

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Longboat Key holiday villa accommodation

Longboat Key villa

2 bedrooms • 2 bathrooms • sleeps 10

from £314 / night

£2,194 / week

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Holiday apartment in Sarasota

Sarasota apartment

1 bedroom • 1 bathroom • sleeps 4

from £48 / night

£284 / week

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Apartment rental in Holmes Beach

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £95 / night

£662 / week

1 / 20

Holiday condo rental

Sarasota condo

2 bedrooms • 2 bathrooms • sleeps 4

from £83 / night

£581 / week

1 / 52

Home rental in Bradenton

Bradenton house

2 bedrooms • 1 bathroom • sleeps 5

from £103 / night

£644 / week

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Holiday home rental

Nokomis house

3 bedrooms • 2 bathrooms • sleeps 8

from £82 / night

£571 / week

1 / 24

Holiday villa in Gulf Gate Estates

Gulf Gate Estates villa

2 bedrooms • 2 bathrooms • sleeps 6

from £99 / night

£687 - £807 / week

1 / 12

Holiday home in Sarasota

Sarasota house

2 bedrooms • 1 bathroom • sleeps 4

from £221 / night

£1,546 / week

1 / 13

Bradenton holiday condo rental

Bradenton condo

2 bedrooms • 2 bathrooms • sleeps 6

from £116 / night

£812 / week

1 / 24

Holiday cottage in Holmes Beach

Holmes Beach cottage

2 bedrooms • 1 bathroom • sleeps 4

from £155 / night

£979 / week

1 / 12

Cottage rental in Holmes Beach

Holmes Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from £155 / night

£979 / week

1 / 13

South Venice holiday home rental

South Venice house

2 bedrooms • 2 bathrooms • sleeps 6

from £129 / night

£816 - £1,297 / week

1 / 25

Holiday apartment in Lido Key

Lido Key apartment

2 bedrooms • 1 bathroom • sleeps 7

from £146 / night

£859 / week

1 / 17

Home rental in Palma Sola

Palma Sola house

3 bedrooms • 2 bathrooms • sleeps 6

from £121 / night

£773 - £1,097 / week

1 / 28

Holiday condo with golf nearby in Longboat Key

Longboat Key condo

3 bedrooms • 2 bathrooms • sleeps 6

from £258 / night

£1,804 / week

1 / 40

Holiday home in Sarasota

Sarasota house

1 bedroom • 1 bathroom • sleeps 2

from £129 / night

£902 / week

1 / 54

Lockwood Ridge holiday home rental

Lockwood Ridge house

3 bedrooms • 2 bathrooms • sleeps 15

from £114 / night

£794 / week

1 / 21

Bradenton holiday bungalow rental

Bradenton bungalow

3 bedrooms • 2 bathrooms • sleeps 6

from £151 / night

£1,052 / week

1 / 14

Apartment rental in Lido Key

Lido Key apartment

2 bedrooms • 1 bathroom • sleeps 6

from £142 / night

£945 - £1,065 / week

1 / 29

Holiday apartment in Lido Key

Lido Key apartment

1 bedroom • 1 bathroom • sleeps 4

from £77 / night

£597 - £769 / week

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Home rental in South Venice

South Venice house

3 bedrooms • 3 bathrooms • sleeps 10

from £159 / night

£996 - £1,028 / week

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