Siesta Key Vacation Rentals

(260 rentals)
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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$463

avg/night

$463
avg per night
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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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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$288

avg/night

$288
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$497

avg/night

$497
avg per 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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Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$338

avg/night

$338
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to uncover Siesta Key's hidden gem - Condo 400! This fourth-floor beauty boasts a jaw-dropping panoramic view of the Gulf of Mexico from the Master Bedroom and a screened-in lanai. With over 1220 square feet of living space, you're in for a treat.This condo is a beach-lover's ...

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Siesta Key Condo

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$316

avg/night

$316
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Come enjoy our unique TWO MASTER BEDROOMS condo! BOTH master bedrooms have the very same beautiful ocean view, and each has it's own "private" access to the lovely lanai! Life doesn't get any better than this, on tropical Siesta Key!!! As you will tell from our pictures, we love the ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$326

avg/night

$326
avg per night
View Details

Key Amenities

  • Pool

About this property

Welcome to Condo 3E, located in the serene paradise of Siesta Key Beach. This beach-themed haven is designed to transport you to a world of relaxation and tranquility. With 1220 sq.ft of living space, two bedrooms, and two baths, you'll have ample space to unwind and rejuvenate.The master bedroom ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$399

avg/night

$399
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Welcome to Siesta Key living in this charming 2nd floor duplex in Siesta Village. This gem offers a perfect blend of comfort and convenience. Nestled in the heart of the village. this unit offers 2 bedrooms and 2 baths with a large shared pool with the unit downstairs. This quaint unit features a washer/dryer ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms

$406

avg/night

$406
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

PRIVATE 3 BEDROOM / 2 BATH HOME LOCATED IN A BEAUTIFUL RESIDENTIAL NEIGHBORHOOD. 1 MILE FROM THE WORLD FAMOUS SIESTA KEY BEACH. FULLY RENOVATED AND NEWLY FURNISHED FOR YOUR ENJOYMENT WITH AN OPEN FLOOR PLAN WITH LOTS TO OFFER. KITCHEN W/ STAINLESS STEEL APPLIANCES AND LARGE PANTRY. 3 LCD SMART TVS, DVD. ...

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Property Type

Siesta Key House

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Siesta Key Apartment
3 BR | 2.5 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2.5 bathrooms

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Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This charming Siesta Key vacation rental home offers a beautiful kitchen, dining area, living room, and outdoor patio. The property includes access to a heated pool shared between the two units in the house. Located in the heart of Siesta Key Village, it's just a 3-minute walk to the #1 beach in ...

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Property Type

Siesta Key Apartment

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Siesta Key Condo | On the beach
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom

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Inquire for rates

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Escape to a tranquil oasis on Siesta Key! This charming studio unit boasts a queen-sized Murphy bed, perfect for a romantic getaway or relaxing retreat. Enjoy breathtaking pool views from the comfort of your own space, and step outside to find yourself mere steps away from the soft white sands and crystal-clear ...

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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 260 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 $160 per night with an average price per night of $336.

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 50 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 54 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!