Siesta Key Vacation Rentals

(281 rentals)
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2 BR | 2 BA | Sleeps 6 | Quick View

$310

avg/night

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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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

"Beautifully renovated beach condo"

The condo contained anything and everything need to have a wonderful vacation. The view of the ocean was spectacular.

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Studio | 1 BA | Sleeps 3 | Quick View

$143

avg/night

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Key Amenities

  • Pool

About this property

GROUND FLOOR STUDIO LOCATED IN THE MIDDLE OF THE CASA MAR COMPLEX. SHORT DISTANCE FROM THE BEACH AND ONE OF THE TWO POOLS IS DIRECTLY ACROSS THE UNIT. QUEEN MURPHY BED, 32 INCH FLAT SCREEN TV. 1 COVERED PARKING SPACE. COMPLEX OFFERS 2 POOLS, TENNIS, SHUFFLE BOARD AND BEACH CHAIRS. HIGH SPEED INTERNET ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$308

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLTop beachfront unit at Fisherman's Cove!! Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 7 | Quick View

15
owner special
Owner special: Please Inquire about SPECIALS for any remaining weeks this Summer!

$263

avg/night

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Key Amenities

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

About this property

The Gulf of Mexico is only 100 ft. from your private sand beach and lanai entrance. Listen to the surf from your master bedroom. Enjoy dining on the lanai while watching the sunset. During the day you can see dolphins, kite boarding and sea birds. This unit has all the comforts of home plus a full size ...

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Property Type

Siesta Key Condo

"Clean & Well Stocked"

Three very important things to make your vacation complete; cleanliness is number one of course, location and is the rental property well stocked so you have everything that is needed for a vacation of ...

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Key Amenities

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

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened ...

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Property Type

Siesta Key House

"Perfect Getaway!"

We SO enjoyed our stay there! Our stay was to celebrate a milestone birthday of our sister and we couldn't have asked for a better spot! Our main goal was to relax, catch up and enjoy the beautiful beach ...

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2 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 0.0 miles to Siesta Key

$279

avg/night

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Key Amenities

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

About this property

Escape to your private oasis on Siesta Key! This spacious villa offers the best of both worlds: direct access to the #1-rated Siesta Key Beach through your own private beach area, and stunning views of the Intracoastal Waterway where you can watch boats go by or launch your own kayak.Unwind in comfort ...

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Property Type

Siesta Key Villa

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3 BR | 3.5 BA | Sleeps 5 | Quick View

5

Distance to beach: 0.3 miles to Crescent Beach

$342

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

6828 Midnight Pass Road is a townhouse style condo three level unit with 3 main bedrooms plus a bonus bath and laundry on the ground floor. Each bedroom has a queen bed, and all furniture and mattresses were purchased new in 2020. Brand new exterior paint and roof in 2024.Convenient and Easy: 3-minute ...

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Property Type

Siesta Key Townhome

"Best vacation ever!!"

We cant say enough about how beautiful this townhouse was, fully stocked with everything, (the blender was great to have because we love our mudslides out by the private pool) The location was unbelievable, ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the ...

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Property Type

Siesta Key Condo

"good place"

Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate

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1 BR | 1 BA | Sleeps 3 | Quick View

8

Distance to beach: 150 yards to Crescent Beach

$277

avg/night

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Key Amenities

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

About this property

1 Week Minimum Stay Required except during Feb 1 to the first Saturday after Easter when 2 weeks are required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great ...

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Property Type

Siesta Key Condo

"Georgious Siesta Key Condo"

This condo is perfectly located in the middle of Siesta Key, on the beach. It is a short distance to Siesta Key Village, that has shopping and restaurants. The condo is very comfortable, with up to date ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

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Property Type

Siesta Key Condo

"Beach and ocean waves"

The condo was super nice. The master bedroom mattress was amazing for a rental. So often I feel like they are hard as rocks but this one wasn’t. The second bedroom had similar mattress but they were not ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$166

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

4TH FLOOR BAYSIDE, 2 BEDROOM / 2 BATH CONDO LOCATED IN THE CAPRI BUILDING OF THE EXCELSIOR COMPLEX. THE COMPLEX HAS 2 POOLS (ONE ON BEACHSIDE AND ONE ON BAYSIDE) WITH HOT TUB, 3 LIGHTED TENNIS COURTS, OUTDOOR BARBECUE / PICNIC AREA AND BEACH ACCESS. UNIT OFFERS WASHER / DRYER, HIGH SPEED INTERNET SERVICE, ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

1

$143

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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2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.1 miles to Crescent Beach Siesta Key

$170

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to The Anchorage Yacht and Tennis Club across from the beautiful sands of Crescent Beach on Siesta Key. Sitting directly on the intercoastal waterway where you can park your boat, jet ski, kayak, and paddleboard. This complex has an Olympic size pool, three lighted tennis courts, pickleball nets. ...

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Property Type

Siesta Key Condo

"June Trip"

Check in was easy. Clean unit. Management staff were friendly and helpful. Beach area use could be more clear. The beach accessories were good.

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3 BR | 3 BA | Sleeps 6 | Quick View

8

Distance to beach: 0.3 miles to Crescent Beach

$353

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to your perfect vacation home on Siesta Key! Our turnkey townhouse is located just a few minutes' walk from the #1 ranked Crescent Beach, where you can enjoy the crystal-clear waters and powdery white sand that have made Siesta Key world famous.Our townhouse features a spacious courtyard ...

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Property Type

Siesta Key Townhome

"Paradise!"

The place was immaculate and had everything we needed. It was so nice to have beach towels, chairs, and sand toys provided. The location is perfect. It's a very short walk to the beach. Some restaurants ...

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3 BR | 3 BA | Sleeps 6 | Quick View

$790

avg/night

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Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool

About this property

**Any advertised discounts on website do not apply to this unit*** 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. also the spiral staircase from this units balcony ...

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Property Type

Siesta Key Condo

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2 BR | 1.5 BA | Sleeps 4 | Quick View

30
owner special
Owner special: End of July 22 through August is now available!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$171

avg/night

View Details

Key Amenities

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

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

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Property Type

Siesta Key Condo

"Great Location!"

Love the location, close to beach and town! Walk to everything. The back patio was a plus!! I would recommend!

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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 400 yards to Siesta Beach

$197

avg/night

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Key Amenities

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

About this property

Spectacular long Siesta beach and Gulf of Mexico views from this gorgeous 2 BD, 2 bath unit. It has was fully remodel in a high quality fashion. The unit is furnished first class and with all the features you could want for a fun vacation! The resort style condominium has three pools, large ponds, lighted ...

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Property Type

Siesta Key Condo

"Great property !"

Beautiful home with all the amenities. Very private location on Azure Way in great neighborhood, but still close to beach & restaurants. Excellent communication with David & owners. Highly recommend.

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3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 1 miles to Turtle Beach

$146

avg/night

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Key Amenities

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

About this property

This waterfront 3 bedroom Bungalow is nestled in an upscale area on Siesta Key between Turtle Beach (1 mi.), Crescent Beach (.5 mi.) and Siesta Key Beach (3 mi.) Free trolley can transport you to the beaches and restaurant in The Village. Enjoy your private dock on beautiful Heron Lagoon watching the ...

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Property Type

Siesta Key House

"Interior Designer"

The Bungalow is well designed as a beachy vibe...great location right on Midnight Pass. It is located at the quieter end of the key which we found more relaxing...great walking. The owners of the Bungalow ...

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3 BR | 2 BA | Sleeps 8 | Quick View

1

$353

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this ranch style home delivers on location and lifestyle. Featuring three bedrooms and two baths and a one-car garage, laundry room with washer and dryer. Gorgeous heated pool looks out to the grand canal, boat dock available to launch ...

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Property Type

Siesta Key House

"Beautiful!"

Siesta 4 rent was very accommodating and responsive. It was very clean and great location. Would definitely rent again! Thank you!

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Key Amenities

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

About this property

You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...

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Property Type

Siesta Key Condo

"What a Fantastic Little Gem!"

Siesta Key have become our favorite vacation spot and #409 at Crescent Royale was where my wife and I got to experience the very best thanks to Karen who accepted us in her beautiful and awesomely appointed ...

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Key Amenities

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

About this property

Take it easy at this mid-century modern peaceful Siesta Key Beach family & pet friendly getaway. 3 BD, 2 BA’s & 2 outdoor showers to wash off the sand after beach fun. Don’t forget to bring Fido! Hang out by the fire pit in the evenings while you grill out taking in the ocean air with ...

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Property Type

Siesta Key House

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Key Amenities

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

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

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Property Type

Siesta Key Condo

"Excellent Condo A306"

We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. Everything ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

This outstanding condo, A203, is on the second floor, accessible using the elevator or outside stairwell and is completely renovated with modern tile flooring throughout, updated kitchen and baths, and new furniture! The kitchen has granite counter tops with tiled back splash, and modern appliances including ...

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Property Type

Siesta Key Condo

"We will be back for a third visit!"

Coffee on the lanai, with the Gulf of Mexico right in front of you is the perfect way to start your day. So beautiful and relaxing. It’s really a friendly and safe place to be. Set up you beach chairs, ...

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Key Amenities

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

About this property

March 2024 availability, won't last long, please contact us! This condo has not been a rental in the past, so you will not see reviews yet - but you can see our property management reviews on Florida Rentals #1258, #11647, #11646 & #11645! This vacation rental condo is directly on the beach ...

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Property Type

Siesta Key Condo

"Wonderfully located, fully equipped getaway!"

This condo was perfect for our vacation with my elderly mother. It was just a few steps from the beach and had everything we needed--quality beach chairs, umbrellas. Inside was well-appointed, too. Keurig ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

"Beautiful Condo in a nice quiet area a stone's throw from the beach."

We loved this condo. It was beautiful, newly refurbished and so comfortable. More like a nice family home than just a rental. We loved sitting in the sun on the lanai watching the birds and the beach. ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$197

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This adorable ground floor 1 bedroom unit in the Casa Mar complex on the beach side of Midnight Pass offers screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car. Tennisand Community laundry facilities. Beach chairs are provided by ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

"GREAT!!"

These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.

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4 BR | 2.5 BA | Sleeps 9 | Quick View

$296

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and a one-car garage and washer and dryer. Beautiful hardwood floors, solid wood cabinetry and sleek granite countertops. ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$413

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

$383

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

2 BEDROOM / 2 BATH BEACHFRONT, GROUND FLOOR UNIT LOCATED IN THE CASA MAR COMPLEX WITH THE WORLD FAMOUS SIESTA KEY BEACH JUST A FEW FEET AWAY. COMPLEX OFFERS 2 POOLS, TENNIS, INTERNET ACCESS ROOM, (SIESTA 4- RENT ASSUMES NO RESPONSIBILITY FOR SERVICE OR MAINTENANCE OF COMPUTERS), COMMUNITY LAUNDRY ROOM, ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$278

avg/night

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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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1 BR | 1.5 BA | Sleeps 3 | Quick View

$351

avg/night

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Key Amenities

  • Air conditioning

About this property

**Any advertised discounts on website do not apply to this unit*** UNIQUE 1 BEDROOM TOWNHOUSE OVERLOOKING THE BEACH, 1 BLOCK TO SIESTA VILLAGE, 3 STORY UNIT WITH GARAGE ON 1ST FLOOR AND WASHER/DRYER, BALCONY, MEXICAN TILE FLOORS, KITCHEN, SPIRAL STAIRCASE TAKES YOU TO THE MASTER SUITE ON THE 3RD FLOOR, ...

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Property Type

Siesta Key Condo

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Key Amenities

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

About this property

A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within ...

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Property Type

Siesta Key Condo

"Sisters beach retreat"

First of all Dina and Russ are wonderful hosts and made our stay in B106 very enjoyable. From the moment we walked in to the condo to hear light jazz playing on the TV’s, the mood was set for a relaxing ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$278

avg/night

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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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2 BR | 2 BA | Sleeps 6 | Quick View

$127

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 3RD FLOOR AND IS A 2 BEDROOM / 2 BATH UNIT. COMPLEX OFFERS HEATED POOL, TENNIS, FULL LAUNDRY FACILITY AT COMPLEX, COMMUNITY ROOM AND A SMALL PIER. UNIT HAS WOOD FLOORS THROUGHOUT , LEATHER FURNISHINGS AND ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

$685

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** EXPERIENCE LUXURY AT IT'S FINEST IN THIS STUNNING 2ND FLOOR CONDO WITH PARTIAL GULF VIEW FROM SIDE BALCONY. ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

2

$209

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

$383

avg/night

View Details

Key Amenities

  • Pool

About this property

BREATHTAKING VIEWS FROM THIS 2 BEDROOM / 2 BATH BEACHFRONT, GROUND FLOOR UNIT LOCATED IN THE CASA MAR COMPLEX WITH THE WORLD FAMOUS SIESTA KEY BEACH JUST A FEW FEET AWAY. THE CASA MAR COMPLEX OFFERS 2 POOLS, TENNIS, WIFI, (SIESTA 4- RENT DOES NOT OFFER TECH SUPPORT), COMMUNITY LAUNDRY ROOM, AND 1 COVERED ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 8 | Quick View

$357

avg/night

View Details

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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2 BR | 1 BA | Sleeps 6 | Quick View

10
last minute deal
LAST MINUTE DEAL 5/15 - 6/26: Siesta Key **Rarely open Summer dates -6/14 for 6 nights & 7/ 6-13. Private Villa steps to beach

$208

avg/night

View Details

Key Amenities

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

About this property

Our villa is located in Siesta Key, FL on Crescent (Siesta Key) Beach, FAMOUS for its powdery, sugar white sand and being VOTED #1 Beach in USA. The Beach has complimentary shade cabanas and beach chairsFeatures include 2 Bedrooms, 1Bath sleeping six with 1King and 2 queen beds. The kitchen is furnished ...

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Property Type

Siesta Key Villa

"Enjoyable VacationVilla"

The Villa was perfect for my December trip to Siesta Key! Very clean, appreciated lots of towels (which I find a plus staying other places they skimp on them), kitchen well equipped. Access to the beach ...

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DEAL

3 BR | 3.5 BA | Sleeps 8 | Quick View

$267

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 3 BEDROOM, 3 1/2 BATH UNIQUE PRIVATE HOME LOCATED ON TWO CANALS JUST EAST OF SIESTA VILLAGE. THE HOME WAS BUILT IN THE TRUE SARASOTA SCHOOL OF ARCHITECTURE DESIGN TO TAKE ADVANTAGE OF AIR FLOW AND LIGHT BUT ORIENTED SO THAT YOU NEVER HAVE DIRECT SUNLIGHT AT ANY TIME OF THE DAY. OPEN FLOOR PLAN ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$310

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

BREATHTAKING, DIRECT OCEANFRONT, 2 BEDROOM / 2 BATH UNIT WITH PANORAMIC VIEWS OF THE BEACH AND SARASOTA SKYLINE. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S ( 65 LIV ROOM) I-POD DOCKING STATION, WASHER / ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 8 | Quick View

1

$243

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

20% OFF DECEMBER 2023!!! WELCOME TO PARADISE! COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH GRAND CANAL HOME LOCATED IN THE QUIET NEIGHBORHOOD OF SIESTA ISLES. THIS FABULOUS REMODELED HOME FEATURES A CUSTOM GOURMET KITCHEN AND OPEN FLOOR PLAN PERFECT FOR ENTERTAINING. HIGH-SPEED INTERNET AVAILABLE, ...

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Property Type

Siesta Key House

"522 Canal Rd"

Great vacation rental home with tile floors throughout making it a perfect beach home. The house has four bedrooms three of which have their own private, full bathroom. Siesta-4-Rent Management was great ...

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4 BR | 2.5 BA | Sleeps 10 | Quick View

$616

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Welcome to paradise! Your oasis awaits you. 4 bedrooms, 2.5 bath luxury townhome with a private pool is just 1 block from Siesta Village and only 2 blocks from the beach! Five star amenities include; Fully stocked gourmet kitchen with granite counter tops, top of the line stainless steel appliances, laundry ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$194

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting in both bedrooms, and beautiful crown molding throughout. The kitchen is a chef's dream, ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 8 | Quick View

$280

avg/night

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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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4 BR | 3 BA | Sleeps 8 | Quick View

$347

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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2 BR | 2 BA | Sleeps 6 | Quick View

$306

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Awesome 1st Floor Beachfront! Just outside your sliding doors is the #1 rated Crescent Beach. Condo features sweeping ocean view and super easy access to the beach while maintaining privacy of corner unit. Two bedrooms, two baths. Washer/dryer, Flat screen TVs in bedrooms 60" Ultra High Def 4k TV ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

$153

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Harbor Towers 2nd floor unit located a few blocks south of the Siesta Public beach. Beautiful property located on the intercoastal. Pool and tennis, propane grills and coin laundry on each floor and elevator. NO smoking in unit and NO pets. Units sleeps 4, 1 King and 2 twins. 2 Week min. CLEANING FEE ...

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Siesta Key Condo

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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 281 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 $58 per night with an average price per night of $256.

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 59 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 56 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!