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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Luxury Gulf View Condo - 3rd Level - 2 BR/2 BA - Sleeps 6 – Property 193245

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $995 - $1,495/week
  • Calendar Last Updated On: Oct 10, 2008
Leave your every day worries behind and relax and rejuvenate at this tropical Gulf Coast paradise. Walk the beach that has been recognized as the 'Best Sand Beach in...

Siesta Key's Banyan Tree Beach Resort 'Key West' unit – Property 218253

  • Siesta Key rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, beach, swimming pool
  • $875 - $1,323/week
  • Calendar Last Updated On: Oct 10, 2008
This large, two-bedroom/two-bath deluxe unit comes with a king-size bed, a queen-size bed, and a queen-size sleeper sofa. For your enjoyment, there are three TVs, a...

1st Floor Midnight Cove 1 Condo with Private Beach – Property 318750

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, beach, resort, accept credit card
  • $599 - $1,299/week
  • Calendar Last Updated On: Oct 9, 2008
This desirable first floor condo, located in Midnight Cove I, has everything: King size bed in the master bedroom, two twin beds in the guest bedroom along with a...

Romantic 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: Oct 10, 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...

Siesta Key 'A Barrier Island' Florida's Cultural Coast – Property 188943

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, swimming pool, air-conditioning
  • $1,295 - $1,795/week
  • Calendar Last Updated On: Oct 9, 2008
'Crystal Sands, Siesta Key, Sarasota'-- Swim and play on the beach with the 'whitest finest sand in the world.' Each evening view a magnificent sunset from your...

“MOONMIST” – Luxurious villa with a private hot tub in a 'jungle' setting – Property 207472

  • Siesta Key rental - villa, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, accept credit card
  • $750 - $1,100/week
  • Calendar Last Updated On: Oct 8, 2008
Moomist Villa is an idyllic setting to relax and rewind. It is located within Polynesian Gardens across the street from beautiful Siesta Key beach (Number 3 on the...

Waterfront Condo, Across from Crescent Beach – Property 110128

  • Siesta Key rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, air-conditioning, washing machine
  • Calendar Last Updated On: Oct 8, 2008
Beautifully furnished 2 bedroom, 2 bathroom apartment in luxury building. Brand New Kitchen, Bathrooms And Flooring!! No expense spared...granite countertops,...

Steps from Beach with Gulf Views – Property 119684

  • Siesta Key rental - condo, 1 bedroom, sleeps 4, 1 bathroom, beach, swimming pool
  • Calendar Last Updated On: Oct 8, 2008
Newly furnished carpeted, 1 bedroom second floor condo with new kitchen and appliances with gulf and pool views. Building complex has laundromat, social room, heated...

Spacious Siesta Key Beachfront Penthouse with Open Balcony – Property 400317

  • Siesta Key rental - condo, 1 bedroom, sleeps 4, 1 bathroom, beach, waterfront, air-conditioning
  • $990 - $1,290/week
  • Calendar Last Updated On: Oct 7, 2008
Wonderful 1000 sq ft penthouse condo with additional 200 sq ft open balcony on Siesta Key is a vacation get-away that will stay in your memory forever.

Waterfront Condo on Blind Pass, Siesta Key-Sarasota, FL - – Property 126138

  • Siesta Key rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, 1 half bath, near the ocean, waterfront, swimming pool
  • Calendar Last Updated On: Oct 7, 2008
9028 Midnight Pass Rd, Sarasota FL. Fully furnished condo with fireplace including a complete kitchen with cookware, dishware and utensils.

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
  • $995 - $1,495/week
  • Calendar Last Updated On: Oct 7, 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,...

Siesta Dunes - 20% Discount in October – Property 219661

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, swimming pool
  • $850 - $1,225/week
  • Calendar Last Updated On: Oct 9, 2008
Siesta Dunes is one of the most desired complexes on Crescent Beach. Our condo is on the third floor of Building 1 with a partial gulf view and was recently updated.

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: Oct 7, 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...

Beachwalk -- Luxury Townhouse – Property 218634

  • Siesta Key rental - townhome, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, village, accept credit card
  • $1,495 - $2,045/week
  • Calendar Last Updated On: Oct 6, 2008
Beachwalk is a spacious, three-bedroom/2.5-bath, non-smoking, luxury townhouse with a private elevator and a private pool. It's situated right across from...

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 - $1,700/week
  • Calendar Last Updated On: Oct 6, 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.

Siesta Key Sunsets & Crystal Sands White Beaches on the Gulf of Mexico – Property 309740

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • $1,295 - $1,850/week
  • Calendar Last Updated On: Oct 6, 2008
Enjoy year round sunsets on the Gulf of Mexico overlooking the crystal white sands of world-famous Crescent Beach on the Gulf of Mexico as well as the island of...

Full View of the Water - 2 Bedroom/2 Bath Townhome with Garage – Property 193244

  • Siesta Key rental - townhome, 2 bedrooms, sleeps 4, 2 bathrooms, beach, waterfront, washing machine
  • $650 - $1,250/week
  • Calendar Last Updated On: Oct 9, 2008
Relax and enjoy full views of the Bay and the boats and dolphins. This beautiful Mediterranean style 2 bedroom condominium includes a 2 car garage and is located...

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 - $1,995/week
  • Calendar Last Updated On: Oct 10, 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...

Deluxe Gulf-to-Bay 3-bdr. Townhouse/Private Access to Siesta Beach/Feb. open – Property 305951

  • Siesta Key rental - townhome, 3 bedrooms, sleeps 6, 2 bathrooms, beach, resort, accept credit card
  • $1,200/week
  • Calendar Last Updated On: Oct 6, 2008
This townhouse is located within the Gulf and Bay Club Bayside resort on Siesta Key. The location is within walking distance of the Siesta Public Beach and Siesta...

Beach Condo across from Siesta Key Beach – Property 118998

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, resort, swimming pool
  • $750 - $1,025/week
  • Calendar Last Updated On: Oct 6, 2008
Enjoy nature and culture at its best! Light-filled, two bedrooms, two bath, corner unit condo has glass sliders that open to two large furnished balconies.
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