- Gulf & Bay Club Bayside
- Gulf Haven
- Gulf Holiday
- Gumbo Limbo
- Harbor Towers Yacht & Racquet Club
- Harbour Towne Yacht Club
- Horizons West
- House of the Sun
- Inlets
- Island House
- Island Reef
- Jamaica Royale
- La Siesta
- Midnight Cove
- Midnight Cove Bayside
- Midnight Cove II
- Midnight Sea
- Moorings
- Our House at The Beach
- Palm Bay Club
- Peppertree Bay
- Peppertree Gulfside
- Polynesian Gardens
- Private Homes
- Private Homes, Siesta Isles
- Private Homes, Siesta Key Village
- Private Homes: Palm Island
- Private Homes: Siesta Village
- Provincial Gardens
- Sandbox on the Beach
- Sandy Cove
- Sara Sea
- Sarasota By The Sea
- Sarasota Surf & Racquet Club
- Sea Club II
- Sea Crest
- Sea Shell
- Sea Winds
- Shells On Siesta Key
- Siesta Beach House
- Siesta Breakers
- Siesta Dunes
- Siesta Harbor
- Siesta Palms by the Beach
- Siesta Sands
- Siesta Shores
- Summer Cove on Siesta
- Sun & Sea Island Hideaway
- Sunrise Cove
- Sunset Point
- Sunset Royale
- Tortuga
- Twin Banyan
- Twin Palms
- Vista Hermosa
- Whispering Sands
- White Sands Village
- Aloha Kai
- Anchorage
- At The Beach Apartments
- Banana Bay Club Beachside
- Banana Bay Club Waterside
- Banyan Tree Beach Resort
- Bay Oaks
- Bay Tree Club
- Beach Villas
This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
-
Siesta Key Vacation Rentals Show this location only Back to top
-
2 Bedroom-2 Bath Condo
2BR/2BA
–
Sleeps 6
– Midnight Cove Bayside #455297
$980 per week 7 night min stay
-
Beachside Siesta Key 1BR/1.5bath Renovated Condo W/ Low Rates!
1BR+/1.5BA
–
Sleeps 4
– Jamaica Royale #387270
From $763- $1022/wk
-
Lush, Private, and Exotic Bayfront Home with Plenty of Extras!
3BR/2BA
–
Sleeps 7
– Private Homes #390073
$4000/mo, $1500/wk
-
Sunset Royale Luxury Condo #302 in Siesta Key
1BR/1BA
–
Sleeps 2-4
– Sunset Royale #364839
From $699/wk
-
America's #1 Beach - Siesta Key - Studio Condo Beach Side
Studio/1BA
–
Sleeps 2
– Other Siesta Key Properties #385813
$595- $756 wkly
-
Walk to Beach and Shops
2BR/2BA
–
Sleeps 4
– Sea Winds #383612
$575.00- $975.00/wk
-
Sunset Royale Luxury Condo 208 in Siesta Key
1BR+/1BA
–
Sleeps 2-4
– Sunset Royale #366004
$799/wk
-
Park Your Car and Walk to Beach & Siesta Key Village
1BR/1BA
–
Sleeps 2-4
– Gulf Holiday #467460
$125- $175 per night
-
Siesta Key Paradise Like No Other * Beautiful Private Beach
2BR/2BA
–
Sleeps 4
– Sandy Cove #362817
$3400- 3950 monthly
-
Studio Unit Directly on Beautiful Siesta Key Beach.
Studio/1BA
–
Sleeps 2-3
– Sandbox on the Beach #390169
From $161- 238/nt or $1127-$1498 wkly
-
House of the Sun #301gs
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196076ha
$155 - $225 per night
-
House of the Sun #205gs
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196064ha
$155 - $225 per night
-
House of the Sun #207gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196066ha
$155 - $225 per night
-
House of the Sun #504gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196106ha
$155 - $225 per night
-
House of the Sun #316gf
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196089ha
$220 - $312 per night
-
House of the Sun #309gv
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196083ha
$179 - $262 per night
-
House of the Sun #413gf
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196102ha
$220 - $312 per night
-
House of the Sun #209gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196068ha
$155 - $225 per night
-
House of the Sun #403gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196092ha
$155 - $225 per night
-
House of the Sun #215gf
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196074ha
$220 - $312 per night
-
House of the Sun #211gs
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196070ha
$155 - $225 per night
-
House of the Sun #315gf
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196088ha
$220 - $312 per night
-
House of the Sun #411gv
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196100ha
$179 - $262 per night
-
House of the Sun #412gv
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196101ha
$179 - $262 per night
-
House of the Sun #202gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196063ha
$155 - $225 per night
-
House of the Sun #210gv
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196069ha
$179 - $262 per night
-
House of the Sun #407gv
2BR/2BA
–
Sleeps 5
– Other Siesta Key Properties #3196096ha
$179 - $262 per night
-
House of the Sun #303gs
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196078ha
$155 - $225 per night
-
House of the Sun #216gf
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196075ha
$220 - $312 per night
-
House of the Sun #208gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196067ha
$155 - $225 per night
-
House of the Sun #214gv
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196073ha
$179 - $262 per night
-
House of the Sun #305gs
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196080ha
$155 - $225 per night
-
House of the Sun #402gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196091ha
$155 - $225 per night
-
House of the Sun #405gs
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196094ha
$155 - $225 per night
-
House of the Sun #409gv
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196098ha
$179 - $262 per night
-
House of the Sun #406gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196095ha
$155 - $225 per night
-
House of the Sun #313gv
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196086ha
$179 - $262 per night
-
House of the Sun #414gf
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196103ha
$220 - $312 per night
-
House of the Sun #312gv
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196085ha
$179 - $262 per night
-
House of the Sun #408gv
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196097ha
$179 - $262 per night
-
House of the Sun #512gf
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196112ha
$220 - $312 per night
-
House of the Sun #503gs
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #3196105ha
$155 - $225 per night
-
House of the Sun #505gs
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3196107ha
$155 - $225 per night
-
Siesta Bungalow
2BR/2BA
–
Sleeps 4-6
– Other Siesta Key Properties #3190797ha
$100 - $200 per night
-
Siesta Gardens #1
2BR/1BA
–
Sleeps 4-6
– Other Siesta Key Properties #3190802ha
$70 - $139 per night
-
Siesta Gardens #4
1BR/1BA
–
Sleeps 2
– Other Siesta Key Properties #3190803ha
$53 - $130 per night
-
Studio/0BA
–
Sleeps 2-6
– Other Siesta Key Properties #1028250a
€495 - €895 per week - EUR 7 night min stay
-
Luxury Penthouse Condo Right on the Water Gulf-to-Bay Complex
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #304486ha
$124 - $227 per night
-
Wow Factor Siesta Key Beach Gulf Front Condo in Siesta Dunes on #1 Beach in USA
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #175907ha
$207 - $270 per night
- Beach Condo Across from Siesta Key Beach 2BR/2BA – Sleeps 6 – Other Siesta Key Properties #118998ha
- Sarasota Getaway 3 Minute Walk to Siesta Key Beach 3BR/2BA – Sleeps 6 – Other Siesta Key Properties #127546ha
-
Executive Luxury at Siesta Key Beach with Beautiful Sunsets
1BR/1BA
–
Sleeps 2
– Other Siesta Key Properties #12974ha
$84 - $143 per night
-
Off-Season Special 7/20/2013 to 11/31/2013 -$ 2,500.00 Per Month
2BR+/2BA
–
Sleeps 6
– Other Siesta Key Properties #318339ha
$3100 per month 31 night min stay
-
Awesome Siesta Key 1st Floor Condo-Siesta Dunes on the Gulf
2BR+/2BA
–
Sleeps 6
– Other Siesta Key Properties #167343ha
$168 - $232 per night
-
Charming Gulf Front 1916 Siesta Key Beach House with Gazebo 2BR/1BA – Sleeps 6 – Other Siesta Key Properties #117670ha
Special offer discounted beachhouse on Siesta Key!!
May 26, 2013 to Aug 31, 2013
$295 - $325 per night 2-7 night min stay -
Call Bob 502-419-6169 *One of the Largest 2BR Apts* Beach Ranked #1 in USA
2BR+/2BA
–
Sleeps 6
– Other Siesta Key Properties #155188ha
$1850 - $1943 per week 7 night min stay
-
Luxury Private Siesta Key Condo on Award-Winning Crescent Beach
2BR+/2BA
–
Sleeps 6
– Other Siesta Key Properties #386460ha
$164 - $237 per night 3-7 night min stay
-
Island Home in Paradise
3BR+/2BA
–
Sleeps 8
– Other Siesta Key Properties #393812ha
$1253 - $1505 per week 7 night min stay
-
Siesta Key, Florida - Beachfront Condo with Panoramic View!
1BR/1BA
–
Sleeps 4
– Other Siesta Key Properties #9168ha
$135 - $183 per night
-
Deluxe Town Home - Garden Apartment, Private Pool
1BR+/1BA
–
Sleeps 4
– Other Siesta Key Properties #118989ha
$89 - $129 per night
-
El Presidente Renovated Beachfront Condo on White Sand Beach-Discount
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #183651ha
$179 - $278 per night
-
Siesta Jewel Beach House- a Great Place for the Whole Family!
3BR+/2BA
–
Sleeps 8
– Other Siesta Key Properties #339739ha
$185 - $256 per night
-
Luxury Renovation on Crescent Beach - Great Location!
2BR/1.5BA
–
Sleeps 4
– Other Siesta Key Properties #174247ha
$204 - $285 per night
-
My Perfect Siesta Key Beach House, Yours Too ! (Not a Duplex or Condo)
3BR/1BA
–
Sleeps 6
– Other Siesta Key Properties #900795ha
$185 - $328 per night
-
Well Appointed Canal Front Home
4BR/3BA
–
Sleeps 8
– Other Siesta Key Properties #283161ha
$117 - $286 per night
-
Beautiful Gulf Front Condo-Ocean View **Rates Reduced**
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #248795ha
$133 - $242 per night
-
Siesta Key Beach Getaway Cottage - Walk to Beach and Village
2BR/2BA
–
Sleeps 7
– Other Siesta Key Properties #383470ha
$67 - $171 per night
-
Siesta Key Beach House - Pet Friendly! Steps to the Beach!!
2BR+/2BA
–
Sleeps 4-6
– Other Siesta Key Properties #299043ha
$125 - $150 per night 3 night min stay
-
Spectacular Siesta Key Gulf Views. Quiet and Comfortable Nonsmoking Condo.
2BR+/2BA
–
Sleeps 6
– Other Siesta Key Properties #173043ha
$214 - $243 per night
-
Tropical Landscape, Easy Access, Affordable Rates.
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #212206ha
$60 - $143 per night
-
Siesta Key Beach Cottage Across the Street from #1 Beach in USA
1BR/1BA
–
Sleeps 2
– Other Siesta Key Properties #931257ha
$93 - $143 per night
-
Beachfront Property - Luxury Penthouse - Great Location!
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #170390ha
$200 - $286 per night
-
Siesta Bayside: Living on the Water in Siesta Key
2BR/1.5BA
–
Sleeps 5
– Other Siesta Key Properties #323441ha
$53 - $161 per night
-
Luxurious Executive Condo with Beautiful Sunsets at the Beach
1BR/1BA
–
Sleeps 2
– Other Siesta Key Properties #195436ha
$93 - $143 per night
-
Siesta Jewel Villa, Walk to the Beach & Village...or Hang by the Pool
1BR/1BA
–
Sleeps 4
– Other Siesta Key Properties #342421ha
$83 - $139 per night
-
Luxury Beach Condo with Water Views
2BR/1.5BA
–
Sleeps 4
– Other Siesta Key Properties #168878ha
$882 - $1113 per week 7-14 night min stay
-
Sunny Siesta Key Home. Walk to Beach!
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #270636ha
$100 - $186 per night
-
Spacious Vacation Rental Condo with Lagoon Views, Beach Access, and Pool
3BR/2.5BA
–
Sleeps 6
– Other Siesta Key Properties #359425ha
$93 - $185 per night
-
Waterfront Canal~Walk to Beach&Siestavillage/ Pool /Jacuzzi/ Spacious House
3BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #224280ha
$1505 - $2100 per week 7 night min stay
- Siesta Key - Luxury Beachfront Home on One of the Best Beaches in the World. 2BR/2BA – Sleeps 5 – Other Siesta Key Properties #112783ha
-
Luxury Beach Cottage
1BR/1BA
–
Sleeps 2
– Private Homes #213515ha
$200 - $300 per night
-
A Brief Walk to Siesta Key Village and the Beach
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #3497799ha
$185 - $275 per night 3-7 night min stay
-
Walk to the Village or the Beach, Everything is in Reach.
2BR/2.5BA
–
Sleeps 8
– Other Siesta Key Properties #247872ha
$100 - $271 per night
-
Beautiful, Elegant, Quiet Water Front with #1 Beach in the World
3BR/2.5BA
–
Sleeps 2
– Other Siesta Key Properties #935628ha
$1750 - $2093 per week 7 night min stay
-
Siesta Key Boutique Condo on Crescent Beach
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #220617ha
$1249 per week 7 night min stay
- Luxury Condo with Spectacular Ocean Views 2BR/2BA – Sleeps 4 – Other Siesta Key Properties #118026ha
-
Beautiful 2 Bed/2 Bath Beachfront Condo on Siesta Key Beach
2BR/2BA
–
Sleeps 4
– Other Siesta Key Properties #974198ha
$3500 - $5200 per month 30 night min stay
-
Siesta Key Beach #1 in USA Steps to Banyan Tree Beach Resort 'Key West' Unit
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #218253ha
$178 per night 3 night min stay
-
Relax on the Community Private Beach and Walk to Siesta Key Village
2BR/2BA
–
Sleeps 7
– Other Siesta Key Properties #283075ha
$67 - $171 per night
- Condo Rental in Siesta Key Florida - Updated Condo with Beach Access 2BR/1BA – Sleeps 4 – Other Siesta Key Properties #165931ha
- Beautiful Condo Across from Award-Winning Siesta Key Beach! 2BR/2BA – Sleeps 4 – Other Siesta Key Properties #174019ha
-
Private Beachfront and Pool, Tennis Court ,Siesta Key Condo W/ All Amenities
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #294435ha
$164 - $179 per night
-
A Brief Walk to Siesta Key Village and the Beach...
2BR/2BA
–
Sleeps 3-6
– Other Siesta Key Properties #3497900ha
$185 - $275 per night 3-7 night min stay
-
Bring Your Boat and Kayaks! Palm Island Home 2 Blocks to Beach!!
2BR/1BA
–
Sleeps 4-6
– Other Siesta Key Properties #968124ha
$100 - $171 per night
-
Gulf View & Steps from Beach and Village - Luxury Townhouse
3BR/3.5BA
–
Sleeps 10
– Other Siesta Key Properties #231204ha
$162 - $386 per night
- Great Location, as Close to the Beach as You Can Get 2BR/2BA – Sleeps 6 – Other Siesta Key Properties #932030ha
-
Beautiful Townhouse on Siesta Key
2BR/2.5BA
–
Sleeps 6
– Other Siesta Key Properties #246503ha
$100 - $171 per night
-
1 Block to Beach on Siesta Key
3BR/2.5BA
–
Sleeps 8
– Other Siesta Key Properties #211979ha
$100 - $236 per night
-
Great Location, Gulf Views
2BR/2BA
–
Sleeps 6
– Other Siesta Key Properties #259492ha
$239 per night
-
Outstanding Beachview - Totally Updated 3 Bed/3bath Condo
3BR/3BA
–
Sleeps 6
– Other Siesta Key Properties #184010ha
$321 - $386 per night
-
2 Bedroom-2 Bath Condo
2BR/2BA
–
Sleeps 6
– Midnight Cove Bayside #455297
Overview of Siesta Key Vacation Rentals
Siesta Key Condos: Create Your Dream Vacation with Ease
Just off the coast of Sarasota, Florida, you’ll find the beautiful barrier island called Siesta Key. If you are looking for the whitest beaches and the most tropical atmosphere in Florida, then you’ll find it here. Forego bland hotels and make your vacation plan more exciting – Siesta Key condos are the perfect option for you.
Siesta Key beach rentals are an even better option if you long to hear the egrets singing and waves crashing outside your bedroom window. Of course, there are also several Siesta Key resorts to choose from as well.
Luxurious Vacations Start Here: Siesta Key Condos
Siesta Key condos come in a wide variety of options, and they definitely offer you the most in terms of amenities. If the weather might be a little chilly on your trip, don’t fret. Many of the condos have heated pools, so regardless of the weather you can still fit in some swimming time with the family. Looking for a more private getaway? Many Florida condos in Siesta Key even have their own beaches!
Other great features that many of the condos offer include beachfront property, breathtaking views and a variety of bedroom options. This makes selecting perfect Siesta Key beach rentals a breeze for a large family.
Siesta Key Beach Rentals Put You Steps from the Ocean
When you plan a family vacation to Florida, it’s all about the water, right? With all the options available in Siesta Key beach rentals, you won’t be far from sinking your toes into the gorgeous white sand and feeling the surf soak your ankles. Plus, being so close to the water provides you with an excellent view.
Another great benefit is that you are close to any action or events taking place on the beach. In May, for instance, you can see World-class sand sculptures created by amazing artists at the Siesta Key Sand Sculpture Contest.
Stay at Some of the Finest Resorts with Siesta Key Resorts
Even if you prefer having complete control over your vacation, there are times when it's great to get a little pampering at luxurious Siesta Key resorts. If you want to take in 50 miles of canals and waterways from your room balcony, then the Siesta Key resorts will allow you to do just that. You’re also not far from great dining and shopping. And, of course, you're never far from the sand - many of the resorts have private beaches where you can rent bungalows, chairs, water toys, or take advantage of the many entertainment options that may be provided by the resort. No matter which option you choose one thing is sure: Siesta Key will provide you with a vacation full of rest, relaxation and fun