Vacation Rentals & Beach Rentals in Siesta Key

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60 beach rentals

Discover the perfect beachfront getaway with a private pool & hot tub.

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Pool or snooker table Pets allowed

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Price per night from

$855

Indulge in a spacious 4-bedroom rental with private pool and beach access!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Pool or snooker table Pets allowed

All filters match

Price per night from

$976

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Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$491

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$230

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$490

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$905

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$490

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$183

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$516

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$246

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$454

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$267

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$110

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Pets allowed, Pool or snooker table

1 of 2 filters match

Price per night from

$114

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$443

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$423

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$448

Tiny House Siesta - Tiny Aqua Oasis- Tiny House that sleeps 6 comfortably

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$444

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$402

Tiny House Siesta - Eleanor- our bright & beautiful Tiny House near the beach

Siesta Key hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$448

Tiny House Siesta - Tiny House Amy

Siesta Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$378

Tiny House Siesta - Tiny Blue Oasis – a tiny house with 3 Queen beds

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$461

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$339

Hidden gem close to everything

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 13 minutes

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$217

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 14 minutes

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$224

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$321

Lovely Siesta Key house with heated pool - A block away from Siesta beach!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$493

A Shell House Getaway

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$631

Cape Aqua

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great place, super location” We thoroughly enjoyed our stay at your home. It was very spacious, clean and inviting. We had everything we needed and the location is wonderful. Thanks and we would definitly recommend your home to others

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$192

The Treehouse

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$403

A Shell House Compound

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$884

Edgemere

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$268

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$1,001

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

1 of 2 match: Pool or snooker table, Pets allowed

1 of 2 filters match

Price per night from

$166

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