Vacation Rentals & Beach Rentals in Siesta Key

Updating...

age 0-16
34 Results

Relevance

Price: low to high

Price: high to low

Reviews

34 beach rentals

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

Match: Climbing frame Stereo system

All filters match

Price per night from

$266

These homes match some but not all of your filters. Clear all filters

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$716

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$409

Responds fast! avg. 4 minutes

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$139

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$490

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$999

Excellent Location - Gulf/Beach View - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 38 minutes

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$344

Luxury Romantic Oceanfront Siesta Beach Condo #304

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$184

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$310

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: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$224

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: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$165

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$314

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$271

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$401

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$189

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$144

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$144

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$454

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$337

Miramar

Siesta Key townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$287

Fanta-Sea 47; By Beachside Management

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$457

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Location, Very Well Appointed” This house is perfectly located right in Siesta Key Village within an easy walk to shops and restaurants. It is also just a block from the beach. No parking hassles! The house is very well appointed. The owner has thoughtfully provided more than enough coffee for the Keurig, lots of towels, and all needed kitchen utensils, dishes, containers, and cooking supplies, in addition to a beach wagon and chairs. Although not luxurious, this is a very comfortable rental. We also liked the privacy of having our own house. The only negatives were the lack of towel racks in the bathrooms and the lack of hot water in the bathroom with the tub (it remained only warm, even after running for a very long time). The water in the other bathroom was fine.

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$315

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: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$903

Responds fast! avg. 4 minutes

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$329

Responds fast! avg. 4 minutes

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$249

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: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$453

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$802

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$205

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$272

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$500

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$509

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: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$514

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$189

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Stereo system

1 of 2 filters match

Price per night from

$109

×

Also consider