Siesta Key Florida Vacation Rentals

Search 23 Siesta Key vacation rental homes and condos.

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Siesta Key Vacation Rentals

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~ Private Villa on #1 Siesta Key Beach ** GULFSIDE
This Listing Qualifies for the Trusted Seal - All Information is up to date and the Owner in good standing.

Siesta Key Florida

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  • Home,
  • 2 Bedrooms,
  • Capacity 6,
  • $100 to $250 Per Night
View  Private Villa on 1 Siesta

Calling ALL Beach and Sunset Lovers........ If you are looking for a vacation condo rental in Siesta Key, Florida for your Florida holidays and family beach vacation please consider my villa re...
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Siesta Key Beachway Condominium

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 5,
  • $100 to $250 Per Night
View Siesta Key Beachway Condominium

2nd Floor Condo w/ Elevator. 2 Bedrooms (1 Queen; 2 dbl). 2 Baths. Large Closets Open Living/Dining area. Equipped Kitchen (DW, MW, IM). Cable TV in living room and Both Bedrooms. Open living/di...
Sun, Sand & SAVE 25% to 35% at Siesta Breakers #603

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • $100 to $250 Per Night
View Sun Sand  SAVE 25 to 35 at

Sun, Sand & *Save 20% to 35%* per Week at Siesta Breakers #603, Direct-with-Owner "All-In Price" DISCOUNTED RENTAL RATES from $1,097 to $1,795 /Wk & SAVINGS from $390 to $727 /Wk depending on the Seas...
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Sun, Sand & SAVE 25% to 55% at Midnight Cove #532

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • $99 or Less Per Night
View Sun Sand  SAVE 25 to 55 at

*Sun, Sand & SAVE 25% to 55%* per Week at Midnight Cove #532, an Updated, Bayside, Beach Condo with all Gulf Side Beach Amenities Access in Siesta Key, FL at Midnight Cove vacation condominiums ...
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Siesta Key Palm and Bay Club G46 tower rental

Siesta Key Florida

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  • Condo,
  • 1 Bedrooms,
  • Capacity 4,
  • Over $250 Per Night
View Siesta Key Palm and Bay Club

The accolades keep pouring in. Guests and media alike rate the Palm Bay Club as a perfect destination for romantic getaways and family vacations. Treat yourself to an idyllic holiday on Florida&rsq...
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Siesta Key Excelsior Unit 107

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • $100 to $250 Per Night
View Siesta Key Excelsior Unit 107

With the Bay in back and the Gulf in front, our condo at Excelsior 107 sits on a little strip of paradise! Located in a luxurious resort with everything from heated pools and outdoor grills to pr...
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Siesta Key Gulf and Bay Club 207F

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • $100 to $250 Per Night
View Siesta Key Gulf and Bay Club

“...The nicest and most beautiful property on the Siesta Key Beach.” So writes a happy guest - and who are we to disagree? And, now the condo was just upgraded in 2010 with stainless...
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Siesta Key Our House at the Beach 222, with Heated

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 4,
  • Over $250 Per Night
View Siesta Key Our House at the Beach

Just steps from a private walkway to the beach, our townhouse overlooking the lake at Siesta Key is the ideal beach retreat for a family, group of friends, or 2 couples. With a pool, tennis, and pi...
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Siesta Key House of Sun 307

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
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Siesta Key Florida House of Sun 307 rentals condos is very family-friendly, was recently renovated and has sensational sunset and Gulf views. Any questions? How about the added weight of the Trav...
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Siesta Key Siesta Dunes Beach 38A rentals condos Gulf

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
View Siesta Key Siesta Dunes Beach

Do you have children who’ll delight in the geckos and insects they can discover in the garden? Or do you love nature and the sight and scents of tropical flowers? An idyllic ocean side cond...
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Siesta Key Jamaica Royale 91

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
View Siesta Key Jamaica Royale 91

How long does it take you to walk 100 yards? Not very long at all. While on vacation at Crescent Beach, consider that your morning commute - from bed to pool. Enjoy the great convenience of a gro...
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San Marco 611, 6th Floor, heated pool, gulf views,

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 4,
  • $100 to $250 Per Night
View San Marco 611 6th Floor heated

From the lanai overlooking the Gulf Coast in our 6th-floor condo, San Marco 611, you can enjoy spectacular sunsets while sipping a cool drink. Well appointed and perfectly located, our oceanfront...
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Siesta Dunes 201

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
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Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. A...
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Gulf and Bay Club Bayside

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
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The moment you arrive at Gulf & Bay Bayside, you’ll appreciate the beauty, serenity, and charm of this “old Key West” style village. Located on the bay across from Sarasota on w...
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Gulf and Bay 502D will perfectly suiBeach Front, 3

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
View Gulf and Bay 502D will perfectly

Gulf and Bay 502D will perfectly suit six nice people who deserve a month of total reward and relaxation on Crescent Beach. The resort club is unrivalled for repeat guest satisfaction and its locat...
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Palm Bay Club G46 Siesta Key FL, Heated Pool, Gulf

Siesta Key Florida

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  • Condo,
  • 1 Bedrooms,
  • Capacity 4,
  • Over $250 Per Night
View Palm Bay Club G46 Siesta Key

The accolades keep pouring in. Guests and media alike rate the Palm Bay Club as a perfect destination for romantic getaways and family vacations. Treat yourself to an idyllic holiday on Florida&r...
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Tiffany Sands

Siesta Key Florida

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  • Home,
  • 3 Bedrooms,
  • Capacity 7,
  • $100 to $250 Per Night
View Tiffany Sands

Our 3 bedroom beach house is directly on Crescent Beach with full gulf views. It is a spacious 1,800 sq. ft. and newly decorated with a fully appointed kitchen, plus 3 1/2 baths and a 1 car garage. Ea...

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CASARINA

Siesta Key Florida

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  • Condo,
  • 2 Bedrooms,
  • Capacity 4,
  • $100 to $250 Per Night
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Casarina is the most prestigious building on Siesta Key. Our 2B/2B unit has panoramic views of the beach and the Gulf of Mexico from the living room, dining, kitchen and master bedroom. Designer decor...
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Beach Place

Siesta Key Florida

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  • Resort,
  • 1 Bedrooms,
  • Capacity 22,
  • $100 to $250 Per Night
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Five Tropical garden beach cottages located at Siesta Key Beach. Old Florida charm, heated salt water pool, tiki cabana bar, sleep 4 - 6, well stocked and well maintained, family friendly. 15 minut...
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Coquina Villa

Siesta Key Florida

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  • Home,
  • 3 Bedrooms,
  • Capacity 6,
  • Over $250 Per Night
View Coquina Villa

Tropical Setting, With Superior Amenities And Facilities That Will Turn YourSouthwestern Florida Paradise Vacation Into An Unforgettable Experience. Enjoy The Privacy Of A Secluded Drive To Access ...
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Currently displaying listings 1 through 20 of 23 listings.

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