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Watersports Holidays in Siesta Key - Holiday Lettings

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313 properties with watersports onsite or nearby

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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 home rental

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 6

from £300 / night

£1,717 / week

1 / 15

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £216 / night

£1,509 / week

1 / 16

Ski home to rent in Siesta Key

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 4

from £322 / night

£2,254 / week

1 / 22

Siesta Key holiday condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 5

from £271 / night

£1,370 / week

1 / 72

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £72 / night

£499 - £866 / week

1 / 42

Holiday condo in Siesta Key

Siesta Key condo

1 bedroom • 1 bathroom • sleeps 2

from £111 / night

£776 / week

1 / 24

Siesta Key holiday home rental

Siesta Key house

3 bedrooms • 3 bathrooms • sleeps 6

from £292 / night

£2,044 / week

1 / 15

Siesta Key holiday apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £94 / night

£656 / week

1 / 38

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

1 / 28

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £258 / night

£1,804 / week

1 / 26

Siesta Key holiday apartment rental

Siesta Key apartment

1 bedroom • 1 bathroom • sleeps 4

from £128 / night

£897 - £1,137 / week

1 / 27

Siesta Key holiday home rental

Siesta Key house

2 bedrooms • 2 bathrooms • sleeps 6

from £166 / night

£1,160 - £3,531 / week

1 / 18

Holiday townhouse in Siesta Key

Siesta Key townhouse

2 bedrooms • 4 bathrooms • sleeps 6

from £322 / night

£2,254 / week

1 / 38

Holiday condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from £171 / night

£1,112 / week

1 / 21

Holiday apartment with shared pool, golf nearby in Siesta Key

Siesta Key apartment

1 bedroom • 1 bathroom • sleeps 4

from £111 / night

£776 - £1,137 / week

1 / 11

Condo letting in Siesta Key

Siesta Key condo

3 bedrooms • 3 bathrooms • sleeps 6

from £319 / night

£2,229 / week

1 / 18

Holiday condo rental

Siesta Key condo

4 bedrooms • 2 bathrooms • sleeps 8

from £129 / night

£902 / week

1 / 44

Siesta Key holiday villa rental

Siesta Key villa

2 bedrooms • 1 bathroom • sleeps 6

from £395 / night

£2,759 / week

1 / 17

Holiday apartment in Siesta Key

Siesta Key apartment

• 1 bathroom • sleeps 2

from £94 / night

£656 / week

1 / 25

Holiday apartment in Siesta Key

Siesta Key apartment

1 bedroom • 2 bathrooms • sleeps 4

from £121 / night

£1,031 / week

1 / 21

Holiday home rental

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 12

from £429 / night

£3,000 / week

1 / 42

Siesta Key holiday condo rental

Siesta Key condo

1 bedroom • 1 bathroom • sleeps 6

from £151 / night

£838 / week

1 / 21

Townhouse rental in Siesta Key

Siesta Key townhouse

2 bedrooms • 2 bathrooms • sleeps 4

from £128 / night

£896 / week

1 / 28

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

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 1 bathroom • sleeps 6

from £455 / night

£3,180 / week

1 / 21

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 1 bathroom • sleeps 6

from £412 / night

£2,880 / week

1 / 20

Siesta Key holiday hotel apartment rental

Siesta Key hotel apartment

2 bedrooms • 1 bathroom • sleeps 6

from £103 / night

£722 / week

1 / 13

Townhouse rental in Siesta Key

Siesta Key townhouse

3 bedrooms • 3 bathrooms • sleeps 8

from £352 / night

£2,465 / week

1 / 35

Holiday condo in Siesta Key

Siesta Key condo

3 bedrooms • 2 bathrooms • sleeps 8

from £626 / night

£4,376 / week

1 / 17

Villa rental in Siesta Key

Siesta Key villa

2 bedrooms • 1 bathroom • sleeps 6

from £395 / night

£2,759 / week

1 / 17

Holiday hotel apartment in Siesta Key

Siesta Key hotel apartment

3 bedrooms • 3 bathrooms • sleeps 6

from £1,031 / night

£7,213 / week

1 / 30

Condo letting in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 4

from £120 / night

£836 / week

1 / 31

Siesta Key holiday cottage rental

Siesta Key cottage

2 bedrooms • 2 bathrooms • sleeps 6

from £97 / night

£674 / week

1 / 27

Holiday condo in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 5

from £146 / night

£1,022 / week

1 / 23

Holiday hotel apartment in Siesta Key

Siesta Key hotel apartment

2 bedrooms • 1 bathroom • sleeps 4

from £103 / night

£722 / week

1 / 32

Holiday condo with swimming pool in Siesta Key

Siesta Key condo

3 bedrooms • 2 bathrooms • sleeps 8

from £107 / night

£746 / week

1 / 32

Siesta Key holiday villa rental

Siesta Key villa

2 bedrooms • 2 bathrooms • sleeps 5

from £620 / night

£4,340 / week

1 / 23

Apartment rental in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £334 / night

£2,339 / week

1 / 22

Holiday villa in Siesta Key

Siesta Key villa

2 bedrooms • 2 bathrooms • sleeps 6

from £412 / night

£2,880 / week

1 / 16

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