Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

Beach rentals in Siesta Key and Villas - Holiday Lettings - Holiday Rentals Siesta Key

All filters

Filters

404 Holiday homes

Holiday townhouse in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £176 / night

£1,228 / week

1 / 24

Siesta Key holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Awesome experience” This was our first experience renting a condo,and it exceeded our expectations. The location is excellent,close to everything but also feels very private and relaxing. The owners were quick to respond to our inquiries and they provide everything you need for a beach trip. We loved the patio area and spent most our time in the property out there grilling, and hanging out by the hammock. It was also convenient to be able to take our dog for a quick potty break right outside in the backyard. Will definitely be coming back,hopefully soon!

from £176 / night

£1,259 - £1,416 / week

1 / 16

Siesta Key holiday apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £248 / night

£1,619 - £2,046 / week

1 / 23

Holiday townhouse in Siesta Key

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

from £338 / night

£2,338 - £2,428 / week

1 / 38

Siesta Key holiday condo rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £149 / night

£1,079 - £1,888 / week

1 / 22

Siesta Key holiday condo rental

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £341 / night

£2,385 / week

1 / 25

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,594 - £2,772 / week

1 / 28

Holiday condo in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £315 / night

£2,203 / week

1 / 27

Condo rental in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £333 / night

£2,329 / week

1 / 18

Siesta Key holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £132 / night

£919 - £1,814 / week

1 / 31

Holiday home with swimming pool in Siesta Key

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

from £787 / night

£5,507 / week

1 / 49

Apartment letting in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £196 / night

£1,367 - £2,277 / week

1 / 22

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £208 / night

£1,449 - £2,513 / week

1 / 26

Holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £208 / night

£1,449 - £2,513 / week

1 / 21

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £196 / night

£1,367 - £2,277 / week

1 / 33

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £112 / night

£782 - £1,606 / week

1 / 37

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £208 / night

£1,449 - £2,513 / week

1 / 15

Siesta Key holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £208 / night

£1,449 - £2,513 / week

1 / 29

Holiday apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £132 / night

£919 - £1,814 / week

1 / 26

Holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £132 / night

£919 - £1,814 / week

1 / 39

Siesta Key holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £135 / night

£943 - £1,928 / week

1 / 25

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £208 / night

£1,449 - £2,513 / week

1 / 23

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £196 / night

£1,367 - £2,277 / week

1 / 24

Siesta Key holiday apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £196 / night

£1,367 - £2,277 / week

1 / 17

Holiday condo rental

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £265 / night

£1,851 / week

1 / 45

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 £209 / night

£1,461 - £2,909 / week

1 / 38

Siesta Key holiday villa rental

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £183 / night

£1,277 - £2,059 / week

1 / 25

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £112 / night

£782 - £1,606 / week

1 / 24

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £105 / night

£1,574 / week

1 / 38

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,594 - £2,772 / week

1 / 23

Holiday apartment in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,594 - £2,772 / week

1 / 32

Siesta Key holiday apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,594 - £2,772 / week

1 / 28

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £161 / night

£1,127 - £2,207 / week

1 / 44

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,594 - £2,772 / week

1 / 23

Holiday apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,594 - £2,772 / week

1 / 26

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,594 - £2,772 / week

1 / 31

Siesta Key holiday apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £228 / night

£1,594 - £2,772 / week

1 / 38

Siesta Key holiday apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £161 / night

£1,127 - £2,207 / week

1 / 27

Holiday apartment in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £152 / night

£1,060 - £2,085 / week

1 / 38

Siesta Key holiday condo rental

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £306 / night

£1,794 - £2,792 / week

1 / 24

×

Siesta Key holidays

What was once a secret gem known to only a few, has rapidly become America's darling beach town.

Siesta Key, located in Sarasota County and about an hour south of the Tampa Bay Area, is an eight-mile island accessible by two bridges from the mainland. Sandals and swimming suits are accepted - even expected in virtually all of the restaurants and boutiques that populated the island - especially so of those located in Siesta Key Village. The atmosphere is as cool as the white quartz sands in the daytime, and while libations and celebrations can warm up the evening, you are never to far from a tiki-esque style bar and the quiet sounds of ocean waves gliding up and down the beach.

In 2011, Dr. Beach named Siesta Beach No. 1 in the nation for its sugary white sand. Siesta Key beach is, in fact, almost entirely composed of crushed quarts crystal. This unique composition not only makes this sand sparkle under the Florida sun, but also keeps the sand cool on even the hottest of Florida summer days. The sand is perfect for sculpting, and every year Siesta Key is home to world-class sand sculpting competitions.

Despite its popularity, there are still quiet corners of Siesta to sneak off to and explore.

Turtle Beach located at the southern end of Siesta Key has sand that's a bit coarser. This beach is a great fishing and snorkelling hot spot. The beach has a steeper incline and carries more shells. After a storm beachcombers might even find a petrified shark's tooth. Nearby are restaurants, shopping and a few local nightspots.

Crescent Beach is another quieter spot, just south of Siesta Key Beach. Enjoy the same blue waters in a secluded atmosphere. This area contains coral formations and bright marine life - perfect for diving.

Siesta Key is perfectly fit for families, singles, and couples alike. Lodging accommodations can be found throughout the key, including hundreds of holiday rentals. Though active year round, Siesta Key's peak season runs January through April. Plan to book your stay as soon as possible if your holiday is planned within that duration.

Information provided by:Visit Sarasota County

Top Destination reviews

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach
Mr

My wife and I enjoyed the most wonderful holiday in this excellent villa. It was very comfortable, had everything we needed and more, and is perfectly situated for the beaches and Siesta Key village is a short walk or bike ride away. The pool was a great bonus. All together, this was a great holiday.see more
Siesta Key - 2bdrm on the beach - amazing views!!
Awesome place! Comforts of home, but with an amazing view!!!

Loved our stay. Very comfortable beach getaway. Everything we needed was here. Great sunsets, beach, and pool. Saw two manatee, lots of pelican, and one turtle. The lanai overlooking the beach and water was a real hit! Would definitely stay again! … see more

Also consider