Embracing Nap Time in Siesta Key

The word siesta refers to the tendency to take a little doze in the middle of the afternoon when it doesn’t seem all that important to do anything else. This lovely, lazy feeling will permeate your entire trip to Siesta Key, so ready yourself for lots of reclining.


Of course you’ll have plenty of opportunity to be active, too, and will surely find that your energy levels will be running high once you’ve had the chance to relax and orient yourself to island life.


That’s right, Siesta Key is a barrier island just off the coast of Florida near Sarasota. Renowned for its white sandy beaches and large population of wildlife – including birds, flowers, trees, dolphins and manatees – this destination is packed with more than just napping beach bums.


Water sports are also a popular pastime, such as sailing and snorkeling, so check out the best stretches of coastline to satisfy your need for adrenaline. Try Crescent Beach, Turtle Beach and Palmer Point Beach for a few different perspectives and possibilities, and your days in this idyllic locale will fly by.


Relish the time you have here by picking out a condo or beach house that will complement your explorations (and provide soft beds, sofas and poolside chaises perfect for snoozing in) so you can pretty much bet that all the bases will be covered.


South Central Gulf Coast Florida is bustling with activity, in its own laid-back way, so be assured that you can find what you need somewhere in the area. Everything from antique stores to outlet malls and live theater to pharmacies can be found within a few miles of this quiet key, from Gasparilla to Fort Myers.


Get the rest you need during this vacation; this is the perfect place for it.

Destination: Search

Vacation Rentals in Siesta Key

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Siesta Key, FL. Luxury Beachfront Condominium With Spectacular Ocean Views. – Property 173043

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $1,250 - $1,475/week
  • Calendar Last Updated On: May 8, 2008
Location, Location, Location! We are located directly on the Gulf of Mexico on the best part of Crescent Beach, located in Siesta Key.

*3 Month Minimum Stay* 1,800 Square foot Siesta Key Townhouse – Property 318339

  • Siesta Key rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, beach, swimming pool
  • Calendar Last Updated On: May 8, 2008
Not a typical Siesta Key rental-this townhouse is one of the most upscale addresses located mere steps from the 'award-winning' beautiful white sand beach at...

Island Style Luxury Beach House – Property 168610

  • Siesta Key rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, near the ocean, swimming pool
  • $1,500 - $2,000/week
  • Calendar Last Updated On: May 7, 2008
Enjoy true island living in a beautifully decorated beach house. 3 short blocks to Siesta Key beach, this Key West style home offers a beautiful open-plan layout.

Luxury Penthouse - Siesta Key's Newest Beach Property! – Property 170390

  • Siesta Key rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, beach, swimming pool
  • $1,595 - $2,000/week
  • Calendar Last Updated On: May 9, 2008
Enjoy Luxury living at this brand-new condominium! Designer-furnished top-floor unit with 11-foot ceilings, granite countertops, Poggenpohl cabinets, high-definition...
SPECIAL OFFER! Luxury 2 Bedroom Condo with heated pool March 15 - December 31

Siesta Key 2 Bedroom Luxury Condo with Heated Pools, Tennis & White Sand Beaches – Property 85153

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, air-conditioning
  • $795 - $1,295/week
  • Calendar Last Updated On: May 6, 2008
Located in Siesta Key, Florida. “The Best Sand Beach in America” (according to The Travel Channel). Siesta Key Beach is renowned for its breath-taking sunsets,...

Crystal Sands Villa #7-Beachside Villa- April 5-17 Available – Property 212972

  • Siesta Key rental - villa, 2 bedrooms, sleeps 6, 2 bathrooms, beach, swimming pool
  • $900 - $1,250/week
  • Calendar Last Updated On: May 6, 2008
Relax in the quiet beauty of Siesta Key. Our gulf-side villa is in one of Siesta Key's most beautiful developments -- only a few steps from the white powder sand of...

Sarasota Getaway 3 Minute Walk to Siesta Key Beach – Property 127546

  • Siesta Key rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, beach, village, swimming pool
  • Calendar Last Updated On: May 6, 2008
Our house is a 3 minute walk to the world famous Siesta Key Beach. It is located on a cul-de-sac which overlooks Siesta Key. Spacious 2200 sq ft with an open floor...

Charming Pool-Front Villa across from Crescent Beach – Property 117588

  • Siesta Key rental - villa, 3 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, swimming pool
  • Calendar Last Updated On: May 8, 2008
This newly renovated villa is conveniently located across the street from the famous white, sugary-soft sand of Siesta Beach in Siesta Key, Florida.

Beach Front Condo on Crescent Beach – Property 121856

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $995 - $1,875/week
  • Calendar Last Updated On: May 6, 2008
Relax in this beautiful fifth floor beach front Condo and enjoy the fantastic direct gulf views from the screened lanai with the beach just steps away!!

Located in the heart of Siesta Key & steps to Siesta Beach – Property 132073

  • Siesta Key rental - villa, 2 bedrooms, sleeps 5, 1 bathroom, beach, village, swimming pool
  • $700 - $995/week
  • Calendar Last Updated On: May 6, 2008
SeaMist on Siesta Key is a casual, fully equipped villa retreat from every day life! Enjoy a refreshing swim in a custom designed backyard pool with its unique...

Siesta Key Comfort – Property 104184

  • Siesta Key rental - condo, 1 bedroom, sleeps 4, 1 bathroom, beach, near the ocean, swimming pool
  • Calendar Last Updated On: May 6, 2008
This is a beautifully appointed, one bedroom condo in a well maintained complex that comes completely ready for your visit. It sleeps four, with a queen-size bed in...
SPECIAL OFFER! $995+ per week, $3,500+ per month April 29 - January 31

Direct Oceanfront, Renovated, Luxury 2 Bedroom Condo with heated Pool and Tennis – Property 172373

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • $1,195 - $1,795/week
  • Calendar Last Updated On: May 8, 2008
Featuring direct ocean front views of the Gulf, this newly renovated Mediterranean style condominium is located ocean side at the Midnight Cove I Condominiums in...

Morgan - Crystal Sands 408 - Completely Renovated Oceanfront Condo – Property 160921

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $1,295 - $1,795/week
  • Calendar Last Updated On: May 5, 2008
*** Two Week Minimum Rental - Non-smoking - No pets *** When you’re seeking a retreat from the ordinary, escape to Morgan Properties' vacation rentals.

Morgan - Crystal Sands 504 Completely Renovated Oceanfront Condo – Property 160923

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $1,295 - $1,795/week
  • Calendar Last Updated On: May 5, 2008
*** Two Week Minimum Rental - Non-smoking - No pets *** When you're seeking a retreat from the ordinary, escape to Morgan Properties' vacation rentals.

Morgan - Crystal Sands 702 Completely Renovated Oceanfront Condo – Property 160926

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $1,295 - $1,795/week
  • Calendar Last Updated On: May 5, 2008
*** Two Week Minimum Rental - Non-smoking - No pets *** When you’re seeking a retreat from the ordinary, escape to Morgan Properties’ vacation rentals.

Morgan - Crystal 803 - Completely Updated Oceanfront Condo – Property 181563

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, swimming pool
  • $1,295 - $1,665/week
  • Calendar Last Updated On: May 5, 2008
*** Two Week Minimum - Non-smoking - No Pets *** When you’re seeking a retreat from the ordinary, escape to Morgan Properties’ vacation rentals.

Live the Dream in this Beachfront Condo with Full Ocean Views – Property 152431

  • Siesta Key rental - condo, 1 bedroom, sleeps 4, 1 bathroom, beach, waterfront, accept credit card
  • $804 - $1,099/week
  • Calendar Last Updated On: May 5, 2008
Siesta Key Beach is 55 steps away from this oceanfront condominium complex. Enjoy unobstructed ocean views from this third floor condo that has been totally...

Charming Beachfront Condo Newly Remodeled with Fabulous Views – Property 150231

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, waterfront, accept credit card
  • $915 - $1,325/week
  • Calendar Last Updated On: May 5, 2008
This quaint 4 story condominium has been described as a 'treasure' by guests. The location is one of the best on famous Siesta Key Beach and offers immediate access...

Siesta Key, Sarasota, Florida - Gulf Vacation Crescent Beach – Property 177476

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • $950 - $1,475/week
  • Calendar Last Updated On: May 5, 2008
You are looking at our Sea Shell Condominium unit #206 Florida home. Our Family is from a small town near Fort Wayne, Indiana.

Great Spacious 3 Bedroom Unit, Bayside at the Beautiful Gulf – Property 155419

  • Siesta Key rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, swimming pool, air-conditioning
  • $1,042 - $1,395/week
  • Calendar Last Updated On: May 6, 2008
Gulf and Bay Bayside is located on Sarasota's Siesta Key with its world famous beach for the finest sand, a true paradise. Gulf and Bay Club has private beach access...
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