Siesta Key Vacation Rentals

(237 rentals)
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3 BR | 3 BA | Sleeps 6 | Quick View

7

Distance to beach: 200 feet to Siesta Key Public Beach

$290

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Single family home with private heated caged pool. Large open floor plan in living area to kitchen and enclosed pool and deck. 3 bedrooms, 2 of which are master suites with ensuite full baths, flat screen TV's, king beds, and sliding glass doors to either caged pool deck or open air sundeck. 3rd ...

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Property Type

Siesta Key House

"Siesta Beach"

Absolutely the best location! House was clean and has everything you need. Especially liked pulling wagon with all the beach items the short distance to the beach. Owners very helpful and quickly replaced ...

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3 BR | 2.5 BA | Sleeps 8 | Quick View

$449

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Enjoy our updated beach front 3 bed 2.5 bath condo. Just steps to the best beach in the world and also steps to beautiful Siesta Key Village entertainment district! All the amenities that you need to have a relaxing vacation.

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 20 feet to Turtle Beach, Siesta Key

$268

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Beautiful beach inspired decor...Fresh, airy and calm...perfect relaxing unit with all the comforts of home and more to enjoy a fun filled time at the beach!!!!!

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

11

Distance to beach: 200 feet to across street

$208

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

2 bedroom gorgeous condo overlooking Siesta Key Beach and Gulf of Mexico. Complex with large community pool, sauna, covered parking, secure gated area. Gas grills, party room, beautiful property. 2 full bathrooms with granite walk in showers and basin, etc. King bed in master with ensuite full bath, ...

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Property Type

Siesta Key Condo

"Beautiful Property with Perfect View"

This property and the entire complex was perfect for our stay on Siesta Key. It was clean and well stocked with everything we needed. We would definitely stay again.

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5 BR | 4 BA | Sleeps 13 | Quick View

11

Distance to beach: 400 feet to Siesta Beach

$794

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. ...

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Property Type

Siesta Key House

"Wonderful home and stay on Siesta Key"

The home was perfect, even nicer than the pictures made it look. Very clean, great layout and integration of the home into the outside pool area. Bathrooms seem recently remodeled and are very clean and ...

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2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 30 yards to Turtle Beach

$268

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Bright and inviting, this popular unit has floor to ceiling sliding glass doors from the lanai, offering breathtaking third floor views. Beautiful white porcelain tile leads to new bamboo laminate flooring, which is just one of the many recent upgrades. The open kitchen has comfortable counter seating ...

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Property Type

Siesta Key Condo

"Holmes Beach Rental"

We loved our visit and loved the condo. The views were amazing . The only compliant would be the living room furniture was not comfortable. And the kitchen could use more kitchen items. But we dealt with ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

MONTHLY RENTAL. Introducing our BEAUTIFUL NEW LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need to cross any streets.Our home away from home is perfect for those seeking a winter retreat or anyone seeking ...

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Property Type

Siesta Key Condo

"CASARINA on Siesta Key Beach-#1 Beach, Place to Visit, Hosts"

To start off with Chris and Jeannie are the best hosts to deal with. Easy going, prompt if anything is needed! They share their lovely home with us vacation lovers visiting literally the #1 Beach-Siesta ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

A spectacular view of Siesta Key’s world-famous white sand beach and the Gulf of Mexico is ready to welcome you to this beachfront 3rd floor unit located in the high-rise. Sunsets can be enjoyed right from your lanai. The apartment is a beautiful, upgraded 2 bedroom, 2 bath unit furnished with ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

The lifestyleLive the Siesta Key lifestyle: • Short walk to the beautiful white sand beaches • Linger in the vibrant cafes and shops of The Village • Kayak along the key’s Grand Canal • Spend afternoons relaxing in the pool • Enjoy Siesta’s famous sunsets ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

This colorful and well cared for unit has a new owner! The view from your lanai will include sunset and will be magnificent! No other property on Siesta Key is built this close to the Gulf of Mexico where you can hear the waves from your lanai and master bedroom windows. The furnishings are very comfortable ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

$248

avg/night

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Key Amenities

  • Kitchen
  • Pool

About this property

Welcome to Paradise, where you can bask in the glory of Siesta Beach, the number one beach in the United States, just 100 steps away from your doorstep! Condo 311 offers 2 bedroom and 2 full Bathrooms featuring over 1220 sf of open living space, with panoramic views of the gulf. Imagine enjoying your ...

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Property Type

Siesta Key Condo

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3 BR | 3.5 BA | Sleeps 8 | Quick View

$611

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Contemporary 3 Bedroom 3 Bath Luxury townhome. Beach views from the 3rd bedroom on top floor with full bath and bonus room and murphy bed. Master suite with tub and walkin shower, Gourmet kichen, leather furniture, balcony with partial views of the Gulf from the 3rd floor balcony. Laundry in unit, 2 car ...

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Property Type

Siesta Key Villa

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4 BR | 3 BA | Sleeps 8 | Quick View

$372

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 4 BEDROOM, 3 BATH PRIVATE HOME LOCATED ON A CANAL IN BEAUTIFUL SIESTA ISLES. OPEN FLOOR PLAN WITH LOTS OF SPACE, HARD WOOD FLOORS, A CAGED PRIVATE POOL WITH STUNNING VIEWS FROM EVERY ANGLE. LAUNDRY ROOM WITH FULL SIZE WASHER / DRYER AND WIRELESS INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE ...

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Property Type

Siesta Key House

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1 BR | 1 BA | Sleeps 4 | Quick View

$149

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Spectacular, modern 1 bedroom , 2nd Floor unit in Siesta Key Village offers great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 1 flat screen TV. Complex offers heated community pool and laundry ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 8 | Quick View

$372

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this totally remodeled modern style home delivers on design, location and lifestyle. Featuring three bedrooms and three baths and a one-car covered parking and laundry room with washer and dryer. Beautiful polished terazzo floors, open ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Luxury water view vacation home only a few minutes from one of the best beaches in the world and #1 in the USA! Like so many others have, make this a yearly vacation spot for you and the family.Our home, located on Siesta Key, with breathtaking intercostal water views is fully furnished with all the ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$220

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

This 1 bedroom is nestled in the middle of the Casa Mar complex on the Beach side of Midnight Pass, Offering ground floor, screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car. and tennis, Community laundry facilities. Beach chairs ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 6 | Quick View

$397

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

BEAUTIFUL, PRIVATE 3 BEDROOM / 3 BATH HOME LOCATED IN THE QUIET RESIDENTIAL NEIGHBORHOOD OF SIESTA ISLES. JUST 5 BLOCKS FROM THE WORLD FAMOUS SIESTA KEY BEACH WITH EASY ACCESS. HOME IS FULLY RENOVATED AND NEWLY FURNISHED FOR YOUR ENJOYMENT WITH AN OPEN FLOOR PLAN WITH LOTS TO OFFER. FULLY EQUIPPED KITCHEN ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$294

avg/night

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About this property

We love our view and we're sure that you will too. Walk on the beach or to the village for that tropical vacation of a lifetime. We're sure that you will love our little portion of paradise and agree that there is nothing like the sunrises and sunsets that we have to offer on Siesta Key. Start ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 8 | Quick View

$647

avg/night

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Key Amenities

  • Air conditioning

About this property

3 Bedroom/ 3 Bath Beachfront Townhome in Siesta Village, offering beautiful sunsets from your 2 balconies. Note that the beach directly in front of the property is private and may not allow access. Public beach access is always available just a few steps away. Go a block behind the unit to all the restaurants ...

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Property Type

Siesta Key Condo

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2 BR | 2.5 BA | Sleeps 6 | Quick View

$138

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$425

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

***20% off stays in January 2024*** BEAUTIFUL BEACHFRONT CONDO WITH VIEWS FROM LIVING ROOM AND BOTH BEDROOMS. BEACH CHAIRS PROVIDED ON THE BEACH. LARGE LANAI RUNS ENTIRE WIDTH OF UNIT. LEATHER FURNITURE, ONE OF OUR MOST POPULAR UNITS. BIG SCREEN TV, VCRand DVD, TV IN EACH BEDROOM. WASHER and DRYER IN ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$643

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

** Due to circumstances out of our control, the pool on the 2nd floor in between the buildings is closed due to refurbishment. You do still have the access to the pool that is on the beach** Luxury at its finest in this 1600 sq. ft. 2006 built Crescent condo complex. This Unique 2 Bedroom 2 Bath on the ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$123

avg/night

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Key Amenities

  • Pool

About this property

NESTLED AMONG THE PALM TREES AND TALL, GRACEFUL OAKS TO THIS ADORABLE AND COMPLETELY REMODELED ONE BEDROOM/ ONE BATH SECOND FLOOR CONDO. BEAUTIFUL MEXICAN TILE THROUGHOUT, LEATHER FURNITURE, COMPLEX OFFERS HEATED POOL, TENNIS AND A SCREENED LANAI OVERLOOKING THE TREE TOPS. UNIT OFFERS WASHER /DRYER, TWO ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 3 | Quick View

$239

avg/night

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Key Amenities

  • Kitchen
  • Pool

About this property

Sandcastles, sunrises, sunsets on Siesta Key! Experience the ultimate Siesta Key vacation with unit 509 - a stunning penthouse on Siesta Key Beach that offers the perfect blend of relaxation and luxury.Located on the top floor, this one-bedroom unit features 820 square feet of cozy comfort with breathtaking ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Vacation rental close to the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.Whether you are looking for a perfect destination for your vacation, a romantic ...

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Property Type

Siesta Key Apartment

"Perfect"

We spent 18 days at the unit. The Unit is beautiful and clean. We enjoyed the location and hope to return next year.

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2 BR | 2 BA | Sleeps 6 | Quick View

$325

avg/night

View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool

About this property

BREATHTAKING GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE BEAUTFUL CRYSTAL SANDS COMPLEX. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH ...

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Property Type

Siesta Key Condo

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Studio | 1 BA | Sleeps 4 | Quick View

3

$146

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

We are proud of our Siesta Key Condo at Ebb Tide. This Florida Beach Rental is in the heart of Crescent Beach. Once you park your car there is no need to use a car for the rest of your stay. A short 1 1/2 block walk and your toes are enjoying the lush, white (quartz) sands of the crescent beach.The ...

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Property Type

Siesta Key Studio

"A little piece of Paradise."

The condo was absolutely amazing, and very affordable. Perfect for a couple, so close to the bay and the beach. The condo had everything needed for our stay. Will definitely book again. I love going to ...

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1 BR | 1 BA | Sleeps 2 | Quick View

$200

avg/night

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About this property

Welcome to this spacious 1 Bedroom 1 Bath unit, covering over 820 square feet of open living space. Located on the fourth floor, this unit comprises a king-sized bed, a fully equipped kitchen, a full bathroom, 2 flat-screen TVs, and a beach kit that includes chairs, a beach umbrella and towels.The ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$325

avg/night

View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool

About this property

GORGEOUS GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE SOUGHT AFTER CRYSTAL SANDS COMPLEX. TILE FLOORS THROUGHOUT KITCHEN, BATHS and LIVING ROOM. 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH SPEED WIRELESS INTERNET ALSO AVAILABLE, (SIESTA 4-RENT IS NOT ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

4

Distance to beach: 0.1 miles to Siesta Beach

$262

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool

About this property

Our new unit are truly a site to see. 2 BR / 2 BATH completely remodeled, newly furnished unit with fully equipped kitchen, cable TV, WiFi, and washer/dryer. Enjoy a Resort Style pool area beautifully landscaped with 2 Tiki Bars and plenty of space to work on your tan! Not to mention a grassed area for ...

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Property Type

Siesta Key Condo

"Paradise"

Our rental was perfect. Clean. Well stocked. The mgmt was awesome w communication and our only issue was a missing hdmi cable for the tv. No big deal but they felt it was and immediately fixed the issue. ...

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2 BR | 2 BA | Sleeps 6 | Quick View

6

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$123

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities 50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

"A Great Home Away from Home"

I loved my two months at Blue Lagoon. It has a great location, near the beach and the village. Palm Island is a great neighborhood, a secluded enclave within Siesta Key. I got to know a lot of my neighbors ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$293

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

2nd Floor, Duplex in Siesta Village. This unit offers 2 Bedrooms and 2 Baths, Shared pool with 303. washer/dryer in unit, screened lanai. Located near quaint shops and restaurants in Siesta Village and about 2 block to the Siesta Beach access. High speed internet- wifi ( Siesta 4 Rent does not offer tech ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$122

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Beautiful 1 Bedroom w/ den in Bayside community of Bay Oaks. 3 TV's, 1st floor unit with new furnishings. Sleeps 4, King in the master bedoom. The den has a twin bed and the livingroom has a sleeper sofa. No cable, Streaming only. Highspeed internet. (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT).1 ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This 4 bedroom 4.5 bathroom condo with elevator, pool and private beach access. No need to look any further as luxury awaits! This unit can be combined with the adjoining unit for 8 bedrooms total. There is a wonderful outdoor living space, living room, dining area, kitchen, office as well as laundry ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$213

avg/night

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About this property

Experience the ultimate beach escape at Unit 110, just steps away from Siesta Key Beach's dazzling, white quartz sand.This 2-bedroom, 2-bathroom unit offers approximately 1,250 square feet of charming living space. Upon entry, you'll be welcomed by a cozy living and dining area that flows ...

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Property Type

Siesta Key Condo

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2 BR | 2.5 BA | Sleeps 6 | Quick View

$463

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

** Due to circumstances out of our control, the pool on the 2nd floor in between the buildings is closed due to refurbishment . You do still have the access to the pool that is on the beach** Beautiful Crescent 2 Bedroom Penthouse Unit with partial Beach views, large balcony overlooking pool area in the ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$248

avg/night

View Details

Key Amenities

  • Kitchen
  • Pool

About this property

Pack your bags and prepare to be swept off your feet by the jaw-dropping magnificence of Siesta Key Beach - ranked numero uno for its powder-soft quartz sand and sunset spectacles! Nestled on the third-floor corner, Unit 301 is a luxurious haven, boasting two bedrooms, two full bathrooms, and over 1220 ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 8 | Quick View

$298

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

CHARMING 3 BEDROOM / 2 BATH PRIVATE HOME LOCATED IN THE QUIET NEIGHBORHOOD OF ISLAND CIRCLE. APPROX. 2 BLOCKS FROM THE WORLD FAMOUS SIESTA BEACH AND APPROX. 1/2 MILE FROM SIESTA VILLAGE. HOME OFFERS A PRIVATE POOL *HEATED ( Nov- April only) , TILE FLOORING, 3 LCD TV’S, IPOD DOCKING STATION, WASHER ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$367

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

COME STAY AND RELAX IN THIS BEAUTIFUL 2 BEDROOM / 2 BATH CONDO LOCATED IN THE PALM BAY CLUB TOWER OVER-LOOKING THE WORLD FAMOUS SIESTA KEY BEACH, ( SAME SIZE AND VIEW AS PENTHOUSE UNIT.) ALL THE AMENITIES. FROM THE TILE FLOORING, GRANITE COUNTERTOPS AND STAINLESS STEEL APPLIANCES TO THE LEATHER FURNITURE, ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 0.5 miles to Siesta Beach access 7

$214

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only**********SPECIAL****** April 2024 - $6900 per month plus utilitiesMay-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 ...

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Property Type

Siesta Key Bungalow

"My stay at the Canal Place in Siesta Bungalows"

I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta ...

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1 BR | 1 BA | Sleeps 4 | Quick View

2

$220

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This 1 bedroom is nestled in the middle of the Casa Mar complex on the Beach side of Midnight Pass Rd. Ground floor unit, screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car, tennis, and community laundry facilities, NO SMOKING in ...

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Property Type

Siesta Key Condo

"Vintage Florida"

Fantastic spot! I would like to book the same time in 2024!Clean, well appointed, quiet. Beach is indescribably spectacular.

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2 BR | 2 BA | Sleeps 6 | Quick View

$293

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

1st Floor Duplex in the Siesta Village. This unit offers 2 Bedrooms, 2 Baths, tile floors, Leather furniture, screened lanai, washer/dryer in unit, pool shared with the 305 unit. Located in Siesta Village near all the restaurants and shops and about 2 blocks to Siesta Beach access. Unit offers high speed ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 10 | Quick View

$284

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 3 BATH UPDATED POOL HOME LOCATED IN A BEAUTIFUL SIESTA KEY NEIGHBORHOOD. HOME OFFERS NEW FURNISHINGS, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, HIGH-SPEED INTERNET WITH BOOSTER, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). ENJOY THE LARGE PRIVATE ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 5 | Quick View

$259

avg/night

View Details

Key Amenities

  • Kitchen

About this property

Condo 4D offers the perfect beach vacation, with its stunning view of The Gulf and Siesta Key Beach from the fourth floor. This 1220 square foot condo features a beachy vibe that will beckon you to enjoy America's top-rated beach.The condo has two bedrooms and two full bathrooms, with the master ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

You have access to a deeded walkway from your condo to the beach while living directly on the intercoastal waterway with a great view. The intercoastal waterway, with its parade of all types of boats and dolphins swimming by, is visible from practically every room. This 2nd floor, 1 Bedroom/1 Bath ...

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Property Type

Siesta Key Condo

"Wonderful!"

This condo is perfect. Comfortable lanai with an excellent view of the intercoastal. Well appointed home (Best one we have ever stayed in). Everything in the condo was organzied and easy to find. Walk ...

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2 BR | 1.5 BA | Sleeps 6 | Quick View

$132

avg/night

View Details

Key Amenities

  • Pool

About this property

April 2024 rates have been lowered. ENJOY THIS SOUGHT AFTER GROUND FLOOR BAY VIEW UNIT WITH LARGE SCREENED LANAI OVERLOOKING THE CANAL. 2 TV'S W/DVD AND GORGEOUS POOL, TENNIS, WASHER DRYER IN UNIT. BEACH ACCESS RIGHT ACROSS THE STREET AND COVERED PARKING. UNIT OFFERS HIGHSPEED WI-FI INTERNET ACCESS, ...

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Property Type

Siesta Key Condo

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4 BR | 2 BA | Sleeps 8 | Quick View

$422

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

A piece of Paradise..... Come relax in this beautiful 4 Bedroom, 2 full bath pool home offering large livingroom and family room, caged heated pool and spa, (spa is non-functional and is maintained at pool temperature.) 1 car garage ( owner keeps one car in garage), washer/dryer. Home located just 1 mile ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 250 feet to Crescent Beach

$332

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Direct-with-Owner Rentals: Siesta Breakers #603 offers "All-In Price" 15% to 30% Discounted Rental Rates from $1,958 to $3,708 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $420 to $913 /Wk from the listed Siesta ...

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Property Type

Siesta Key Condo

"Lovely"

The condo was very clean and comfortable. Beautiful view from the lanai. Great location, walking distance to many restaurants and ice cream parlors!

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1 BR | 1 BA | Sleeps 4 | Quick View

1

$149

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

This 1 bedroom , 2nd Floor unit in Siesta Village offers, great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 2 TV's. Complex offers community pool and laundry facilities located off common ...

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Property Type

Siesta Key Condo

"Siesta Key paradise"

We had a great vacation here! Condo was very nice, clean and well supplied. Close to Siesta Village, Beach and within walking distance of almost everything. A definite hidden treasure!

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Siesta Key Vacation Rentals

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

Find the Beach Vacation of a Lifetime with Siesta Key Vacation Rentals


Interested in a beach vacation for your next spring break or a long weekend away? Though the great state of Florida is known for its many scenic beach towns, there are some that cater more to those looking for a quiet, relaxing trip and some that are perfect for an exciting vacation full of non-stop fun in the sun. What if you could find a beach city that offers the best of both worlds for a truly well-rounded vacation? Enter Siesta Key vacation rentals. 

Nestled just south of Sarasota, Siesta Key, FL, is a spirited city along the Gulf Coast that offers just as many opportunities for R&R as it does for nightlife, watersports, and unforgettable adventures in the great outdoors. Though the island of Siesta Key itself is only about eight miles long, it’s jam-packed with enticing restaurants, unique shops, and glittering white sand beaches as far as the eye can see. 

As a major vacation destination along Florida’s Gulf Coast, there are many hotel options to choose from during your stay, with varying proximities to the beach. However, if you’re looking for a truly immersive experience during your trip to Siesta Key, you won’t get it at a crowded commercial hotel! 

Browse Siesta Key vacation rentals from FloridaRentals to find the perfect rental home for your beach vacation. Whether you’re looking for a sunny, romantic getaway for you and a loved one, or you’re bringing the whole family along, you’re sure to find an incredible property. Look for one that offers authentic local architecture, plenty of space to spread out during your downtime, and close proximity to all of the best features the city has to offer.

Siesta Key, Florida Travel Tips


There’s a reason why oceanside Florida cities like Siesta Key tend to be popular destinations during springtime. While temperatures may be warmest on average in the summer months, this time of year also has the highest levels of precipitation and humidity. Unfortunately, this makes it more difficult to enjoy outdoor activities. 

In mid to late spring, temperatures in the air and water are warm and comfortable without too much rain or humidity expected. This makes it easy to take part in all of your favorite pastimes, including surfing, boating, wakeboarding, or simply catching some rays on the sand. 

The closest airport to Siesta Key is the Sarasota/Bradenton International Airport, which lies around 11 miles north of the city center. Most visitors will fly into this airport for its easy access, though the area can also be reached relatively quickly by way of the Tampa International Airport.

How to Spend Your Vacation to Siesta Key House Rentals


It’s no surprise that most Siesta Key vacationers spend more time at the beach than anywhere else during their visits. The most popular beach destination is Siesta Key Beach, which was ranked the #1 Beach in the U.S. by TripAdvisor’s Traveler’s Choice Awards in 2020. The gentle waves, powdery white sand, ample parking, and plentiful concession stands are just some of the reasons why many visitors choose to lounge their day away at Siesta Key Beach. 
Those who are interested in an unforgettable outdoor experience shouldn’t miss out on a trip out on the water with Adventure Kayak Outfitters. You’ll have the choice of a guided kayak tour of the nearby Exotic Mangrove Tunnels or a kayak rental to make your own adventure. You’re sure to spot some incredible wildlife like dolphins, exotic birds, and manatees along the way.

Yearly Events in Siesta Key


Siesta Key is closely linked with the nearby city of Sarasota. The two cities share many of their annual events, creating even bigger and better celebrations for locals and tourists alike to enjoy. 

One annual event that’s already become a mainstay in the local culture is the Annual Downtown Sarasota Craft Festival. This unique arts and crafts show features a wide variety of media, including pottery, paintings, jewelry, photography, and much more, alongside the scenic white-sand beaches. Visitors can peruse and purchase unique wares from local artisans, including soaps, spices, plants, and even kettle corn. 
Runners visiting Siesta Key can get in a great workout while supporting a great cause at the Annual Andrew Monroe Memorial Scholarship 5K Run/Walk. All funds raised during this event are donated to the Sarasota Community Foundation Scholarship, which helps local athletes train to their full potential and achieve their goals.  

Best Eats Near Siesta Key Rentals


Whether you’re in need of some casual seaside grub for the family after a long day at the beach or looking forward to a romantic date night with your significant other, Siesta Key has a huge variety of delicious and eclectic eateries fit for every taste and occasion. 

For a hearty steak, you can’t do much better than Summer House Steak & Seafood. This stylish eatery offers sustainably sourced steaks alongside a variety of unique sides, salads, beverages, and desserts that are sure to satisfy. Additionally, Summer House offers a full menu of seafood dishes. It takes full advantage of the city’s close proximity to fresh seafood and offers plenty of surf and turf options for hungry visitors. 

Island House Tap and Grill is a local favorite for casual yet memorable eats in Siesta Key. With a varied menu that includes everything from tacos to burgers to ceviche, as well as plenty of refreshing cocktails, you’re sure to enjoy a delicious and satisfying dinner with your family.


FAQ

How many vacation rentals are there in/around Siesta Key?

There are 237 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Siesta Key?

There are vacation rentals available in Siesta Key for as low as $89 per night with an average price per night of $268.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 57 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 53 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!