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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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 6, 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...

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...

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 6, 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...

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...

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.

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.

Spectacular Location - Close to Everything! – Property 172205

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, resort, swimming pool
  • $797 - $1,197/week
  • Calendar Last Updated On: Oct 6, 2008
Escape to tropical paradise in this charming “old Key West” island style village just steps from world famous Siesta Key Crescent Beach.

A Siesta Key Charmer – Property 148494

  • Siesta Key rental - apartment, 1 bedroom, sleeps 2, 1 bathroom, near the ocean, village, air-conditioning
  • $895/week
  • Calendar Last Updated On: Oct 2, 2008
Desirable Siesta Key location close to Village, shopping , dining, entertainment, as well as the famous, sparkling white sands of Siesta Key Beach.

BOATERS WELCOME! Spacious Condo on Lovely Lagoon Across from Gulf – Property 117639

  • Siesta Key rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, near the ocean, resort, swimming pool
  • $650 - $1,150/week
  • Calendar Last Updated On: Oct 2, 2008
Spot manatees, manta rays or dolphins! This spacious, twelve step walk-up corner condo is on a beautiful lagoon just a block from quiet Turtle Beach.

Luxurious Executive Condo with Beautiful Sunsets at the Beach – Property 195436

  • Siesta Key rental - condo, 1 bedroom, sleeps 2, 1 bathroom, beach, waterfront, accept credit card
  • $750 - $1,099/week
  • Calendar Last Updated On: Oct 4, 2008
First floor luxurious executive level totally remodeled one bedroom condo with double french doors that lead to your private patio at the world's best beach, Siesta...

Sophistication, Style & Serenity on Siesta Key: 'Casa de Mariposa' – Property 170576

  • Siesta Key rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, beach, village, accept credit card
  • $2,300 - $2,800/week
  • Calendar Last Updated On: Oct 1, 2008
Vacation effortlessly yet luxuriously in one of Siesta Key's premier beach rental homes. Conveniently located steps away from the famous pristine white beach of...

Sophistication, Style & Serenity on Siesta Key: 'Casa de Mariposa' Townhome – Property 170592

  • Siesta Key rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, beach, village, accept credit card
  • $2,100 - $2,600/week
  • Calendar Last Updated On: Oct 1, 2008
Vacation effortlessly yet luxuriously in one of Siesta Key's premier beach rental homes. Conveniently located steps away from the famous pristine white beach of...

Siesta Sunsets at Fisherman's Cove – Property 202264

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • $995 - $1,645/week
  • Calendar Last Updated On: Oct 1, 2008
You could throw a tennis ball into the gulf from this beachfront vacation condo! Located on Siesta Key in Sarasota, Florida, this vacation home has the best of both...

Siesta Key, Siesta Beach Front Home -on the Beach! – Property 185793

  • Siesta Key rental - house, 2 bedrooms, sleeps 8, 4 bathrooms, beach, waterfront, air-conditioning
  • $1,750 - $3,000/week
  • Calendar Last Updated On: Sep 30, 2008
Siesta Key is ideal for extended family vacations and perfect for a group of friends. Relax and enjoy the spectacular panoramic 180+ degree views of the Gulf of...

Awesome Siesta Key Beach Gulf Front Condo in Siesta Dunes – Property 175907

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, swimming pool
  • $1,150 - $1,750/week
  • Calendar Last Updated On: Sep 30, 2008
Siesta Key is situated on what is known as a barrier island. It measures 7 miles long, lies just offshore from Sarasota, FL. Two bridges connect Siesta Key to the...

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: Sep 30, 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.

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: Sep 30, 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,...

Gulf Front-Completely Renovated-Elegant and Beautiful – Property 190380

  • Siesta Key rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • $1,050 - $1,500/week
  • Calendar Last Updated On: Sep 30, 2008
COMPLETELY RENOVATED New bathrooms, kitchen, cabinets, granite counters, floors, decorative molding, doors, tile and carpet, flat screen TV, furniture,...

Midnightnight Cove II – Property 217665

  • Siesta Key rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, 1 half bath, beach, waterfront, accept credit card
  • Calendar Last Updated On: Sep 30, 2008
This unit has been recently remodeled with granite counters, tile floor and all new furniture. It is a 2-bedroom/1.5-bath condo features a private balcony...
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