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Family Friendly Holidays in Siesta Key - Holiday Lettings

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Siesta Key holiday apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £184 / night

£1,287 - £2,281 / week

1 / 59

Holiday townhouse in Siesta Key

Siesta Key townhouse

1 bedroom • 1 bathroom • sleeps 4

from £246 / night

£1,718 / week

1 / 24

Siesta Key holiday home rental

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 6

from £301 / night

£1,721 / week

1 / 15

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £216 / night

£1,513 / week

1 / 16

Holiday apartment in Siesta Key

Siesta Key apartment

1 bedroom • 1 bathroom • sleeps 4

“What a great place!!” Beautiful location, very nice and clean. Very cold aC unit if you so desired. Great location, will be back every year.

from £78 / night

£560 - £818 / week

1 / 30

Holiday condo in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from £241 / night

£1,688 / week

1 / 27

Cottage rental in Siesta Key

Siesta Key cottage

2 bedrooms • 2 bathrooms • sleeps 6

from £198 / night

£1,386 / week

1 / 24

Ski home to rent in Siesta Key

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 4

from £323 / night

£2,260 / week

1 / 22

Siesta Key holiday condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 5

from £272 / night

£1,373 / week

1 / 72

Apartment letting in Siesta Key

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 8

from £221 / night

£1,545 - £2,828 / week

1 / 49

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £72 / night

£501 - £868 / week

1 / 42

Siesta Key holiday hotel apartment rental

Siesta Key hotel apartment

3 bedrooms • 1 bathroom • sleeps 6

from £109 / night

£760 / week

1 / 14

Condo rental in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 8

from £267 / night

£1,868 / week

1 / 18

Holiday villa rental

Siesta Key villa

3 bedrooms • 3 bathrooms • sleeps 8

“Beachwalk B” We were in Siesta Key for an extended family vacation/small reunion and found the area to condusive to our needs. The townhouse was clean and lovely and convenient to the beautiful beach as well as the village. We would return here again.

from £185 / night

£1,287 - £2,673 / week

1 / 60

Holiday condo in Siesta Key

Siesta Key condo

1 bedroom • 1 bathroom • sleeps 2

from £111 / night

£778 / week

1 / 24

Siesta Key holiday condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 4

from £142 / night

£732 - £1,033 / week

1 / 32

Siesta Key holiday home rental

Siesta Key house

3 bedrooms • 3 bathrooms • sleeps 6

from £293 / night

£2,049 / week

1 / 15

Holiday townhouse in Siesta Key

Siesta Key townhouse

3 bedrooms • 3 bathrooms • sleeps 6

from £198 / night

£1,386 / week

1 / 16

Holiday apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £232 / night

£1,621 / week

1 / 26

Siesta Key holiday home accommodation

Siesta Key house

2 bedrooms • 2 bathrooms • sleeps 6

from £157 / night

£1,356 / week

1 / 35

Siesta Key holiday condo rental

Siesta Key condo

1 bedroom • 1 bathroom • sleeps 4

from £172 / night

£1,119 / week

1 / 18

Holiday home with swimming pool in Siesta Key

Siesta Key house

5 bedrooms • 3 bathrooms • sleeps 12

from £2,148 / night

£15,034 / week

1 / 25

Condo rental in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from £181 / night

£1,266 / week

1 / 14

Holiday condo with swimming pool in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 5

from £95 / night

£663 / week

1 / 40

Holiday condo rental

Siesta Key condo

2 bedrooms • 1 bathroom • sleeps 4

from £125 / night

£732 - £861 / week

1 / 21

Holiday apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £197 / night

£1,383 - £2,548 / week

1 / 31

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 £351 / night

£2,454 / week

1 / 28

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £130 / night

£904 - £1,812 / week

1 / 28

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

“Awesome Stay at Fisherman's Cove” My husband and I visited Siesta Key for our anniversary. Having never been there, we weren't quite sure what to expect. Everything (the condo, location, beaches, weather, sunsets, etc.) exceeded our expectations. Oh and how could I forget the welcome bottle of wine! The condo is located on the quiet part of Siesta Key so if you are looking for lots of RNR, this is the place to be. The unit was well appointed with everything you needed. It was great to be able to walk right out the lanai and be on the beach. All the little extras were appreciated too (beach chairs, beach towels, umbrellas, kayak, etc.) And, last but not least, the service provided by Lisa was superior. Ease with making reservations, signing of the contract, information provided to us on accessing the unit, directions, etc. was just top quality. After we left to head home, my husband couldn't find his watch. We were contacted by Lisa stating the cleaning crew found a watch and that they would mail it to us. How is that for service? Just outstanding. Thanks for everything. We will be back and will definitely be recommending Fisherman's Cove and Sunnyside Properies to our family and friends.

from £197 / night

£1,383 - £2,548 / week

1 / 35

Apartment rental in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

“As close as possible to a beautiful beach!” This was the most beautiful beach our family had ever been to on vacation. The beach was not crowded at all and it was like being on your own private beach. The condo was only steps away from the beach.

from £197 / night

£1,383 - £2,548 / week

1 / 39

Apartment rental in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

“Pure relaxation” We have been vacationing in Manasota Key for over 10 years. The condo we have rented the past 3 years in a neighboring complex was booked so we thought we'd give this unit at the El Galeon a try. Loved it! Was perfect for a family or small group. Couldn't be closer to the beach or pool. It had everything we needed for the week including beach chairs, towels and sand toys. It also had TVs in each bedroom so kids and adults happy. It was not the fanciest unit we have rented, but everything was clean and in good condition and the price was much better than we have paid for more upscale units. We had a great week at El Galeon and hope to rent this unit again next year.

from £197 / night

£1,383 - £2,548 / week

1 / 29

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

“The perfect condo in the perfect beach location on Siesta Key!” My husband and I rented this condo on a last minute decision to visit Siesta Key instead of Sanibel island, (glad we did!). The condo was perfect. First off, Sea Shells is located on the beach, across the street from the 'South Village'. Our section of beach was graded almost every day we were there. It was busy, but not packed like the public beach. It was also great being right across the street from the grocery store, bike rental store and several bars and restaurants..Clayton's restaurant was amazing! The condo itself was updated, spacious, clean and nicely decorated. They had every amenity we could need including a high chair and portable crib for our 10 month old! The living room had comfty furniture and a big flat screen and the kitchen was very well equipped. Beach towels, chairs, umbrella etc were provided...The only advice we have is to remember to get coins for laundry - there's a bank across the street from Clayton's.

from £142 / night

£986 - £1,941 / week

1 / 32

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £197 / night

£1,383 - £2,548 / week

1 / 64

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £117 / night

£650 - £1,315 / week

1 / 38

Siesta Key holiday condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from £185 / night

£1,287 - £1,812 / week

1 / 24

Siesta Key holiday apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £163 / night

£1,141 - £2,415 / week

1 / 69

Holiday apartment in Siesta Key

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 8

“Excellent accommodation, brilliant location” Stayed here with my wedding party from the UK and found the accommodation equipped with everything we needed and more.Brilliant location near the beach and all that Siesta Key Village has to offer. Lovely pool area. Greg, the local contact was great..nothing too much trouble and Lisa and Dan were wonderful to deal with. Thank you for making our wedding perfect.

from £221 / night

£1,545 - £2,828 / week

1 / 45

Holiday apartment in Siesta Key

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 8

“Perfect rental for family vacation” The 3 BR/2BTH condo was perfect for our family vacation with our daughter, son-in-law,and boys, ages 4 and 1 1/2. The rooms are very spacious,and there is excellent storage, updated bathrooms and kitchen, new TVs and comfortable beds. The bedroom furnishings were attractive and provide ample storage. Having our own washer and dryer, in the condo, was invaluable. The views are worth a million dollars and having the beach just outside the door was wonderful. The pool was heated and the grounds are impeccable.The unit was spotless and there were plenty of towels, sheets and there were even sand toys for the children. Situated off the beach road, it was quiet and peaceful, unlike condos that are closer to Siesta Key Beach. The fantastic Siesta Key Beach, is however, is only a 5 minute drive away. The location of Fisherman's Cove is very convenient to reach restaurants, shopping, golf, and other attractions in the area. And it could not be more perfect if you have a fisherman in your group. My son-in-law and grandson fished in the gulf and off the piers on the lagoon and were in heaven. The living room/dining room furniture was somewhat worn, but not shabby and still functional. We will definitely return! The sunsets were just amazing!

from £221 / night

£1,545 - £2,828 / week

1 / 44

Holiday apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £259 / night

£1,808 / week

1 / 26

Siesta Key holiday home rental

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 6

from £130 / night

£904 / week

1 / 13

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