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Vacation Rental By Owner Siesta Key Florida

The Rent Siesta Keys Difference

Siesta Key Florida Condo Rental By Owner

Large Selection of Rentals

We offer an unrivaled selection of rental Siesta Key Vacation Rentals, as well as properties throughout the Sarasota and Bradenton Gulf Coasts. Discover a spectacular paradise where the timid emerald waters meet beach side villages.

Over 15 Years of Experience

One of the first and most reputable professional vacation rental management firms in Sarasota focused solely on providing accommodations to Siesta Keys visitors with over 50,000 guests served.

Most Competitive Rates

Book with us to ensure you get the best price guaranteed. With no booking, processing, or admin fees, our rates are unbeatable. A wide variety of affordable rental properties in the keys that dont break your wallet. Book our Siesta Key Luxury Rentals Today!

Something Tropical In Siesta Key

The palms and Caribbean-esque sands of Siesta Key should be a clue to the island’s tropical nature. Enjoying year-round warmth and 100s of days of sunshine, there’s never really a time when the board shorts and bikinis aren’t needed. Loads of people will head down during the US winter. Temperatures average around 6274 between December and March, and there’s hardly any rain at all you’ll get a tan while the snows fall in the Midwest. Summer, from June to September, is the hottest time. It also brings more chance of rain and the occasional tropical storm.

Cool Tours And Excursions From Siesta Key

Siesta Key offers various kayaking tours in the shallow, Intracoastal channel, where you can see different species of birds, fish, and shellfish. The tours usually happen on single kayaks and make for an adventurous time. Go for a parasailing tour if you want to enjoy a breathtaking view of the pristine coast and the shimmering waters.

Scuba diving remains one of the more popular activities on Siesta Key. The warm weather allows for diving around the local artificial reefs and natural areas all through the year. You can choose from a diverse range of scuba diving tours operated by professional companies. They offer everything from relaxing recreational and to full technical diving trips.

Floridas west coast is one of the best places to do a fishing tour. There are many private tour companies to provide you with all levels of fishing experience both onshore and offshore. Also, do take a guided culinary tour in Siesta Key as they are entertaining, interesting, informational, and most of all will satiate your taste buds like nothing else. They also provide a sneak peek into the rich history of the place. You can ask the management at your vacation rental to find out about the best companies for each of the tours.

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Things To Do In Siesta Key

Siesta Key is small, but there is still plenty to do whether you want to explore the beach and indulge in water sports or enjoy some upscale shopping and dining. Here’s a round-up of some of our recommended activities on Siesta Key to curate your own wish-list of what to see and do.

  • Breathtaking beaches – Siesta Key Beach, Crescent Beach, Sarasota Beach and Turtle Beach
  • Smaller beaches for tranquility like Shell Beach
  • Point of Rocks outdoor attraction for fishing, shelling, and viewing birds and marine wildlife
  • Boating
  • Sun Garden Cafe

The Best Beaches To Book A Siesta Key Rental Near


Watersport lovers will have a blast in Siesta Key its the ultimate beach destination. Its four main areas are: Siesta Beach, Crescent Beach, Turtle Beach and Siesta Key Village. When staying in your Siesta Key vacation rental, try visiting each one, as they all have a unique charm.

1. Siesta Beach

The most popular, Siesta Beach, was in fact rated the number one beach in the United States in 2011. Here, you can lounge on its lovely quartz sand, enjoying the cool feeling under your toes. Try some active sports in the tennis and volleyball courts, or go with your family for a picnic. Siesta Beach is ideal for swimming, as the water is shallow near the shore and there is lifeguard protection all year round.

2. Crescent Beach

For catching the gorgeous sunset, head to Crescent Beach. It is an area rich in coral and active marine life. The pristine white sands of the beach are ideal for sunbathing. With its stunning blue waters and peaceful vibe, its also a great place for a romantic date with your favorite person.

3. Turtle Beach

Youll find Turtle Beach on Siesta Keys southern tip. Its notably darker sands have more shells, so if you love collecting, or have little ones who do, head there. There are also playgrounds and areas for playing sport on the sand. Turtle Beach is known mainly for a large number of sea turtle nesting on its shore. The area is a popular spot for embarking on boating rides, paddleboarding, kayaking, canoeing, and jet skiing.

4. Siesta Key Village

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Transportation On Siesta Key

Although you will need a taxi service or rental car to get from your airport of choice to Siesta Key, there are plenty of nearly-free transportation options once you’re on the island. Here’s our list of transportation options to and around Siesta Key for a successful vacation.

  • Conscious Cab of Sarasota

If you need a taxi around the key , Conscious Cab of Sarasota is ready to deliver. Book a ride to or from the airport, or get in touch for an excursion off of Siesta Key. Call 941-306-6653 to get in touch whether you’re going on a brief journey or long-distance car transportation.

  • Johnny’s Original Free Rides

Johnny’s was the first company to offer free transportation around Siesta Key with service from Siesta Key Village all the way to Turtle Beach on the opposite end. Rides are free, but you’re expected to tip generously. The team offers rides from 10 a.m. to 2 a.m. daily. Call 941-928-9200 for more information or to set up your free ride.

  • Sun Ride Pedi Cab

Sun Ride Pedicab in Siesta Key prides itself on being the only true “eco-friendly” tour and transportation service. Rides around the Key are free, but drivers expect you to tip generously. Call 941-343-3400 to get in touch with Sun Ride Pedicab.

  • Siesta Key Breeze Trolley

Take a charming trolley ride around Siesta Key for free with the Siesta Key Breeze Trolley. You’ll get to skip the parking or traffic battle during peak tourist season. Call 941-861-1234 for more information.

  • Siesta Key Free Ride
  • Siesta Key Frog Hop

Southwest Florida International Airport

The Southwest Florida International Airport is 89 miles from Siesta Key taking 1 hour and 30 minutes.

Airlines: Air Canada, airBerlin, American Airlines, Delta, Frontier, JetBlue, Silver Airways, Spirit, Southwest Airlines, Sun Country, United, and West Jet.

Public transit, car rental, and taxis, limos, Uber, and Lyft are available.

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Island Paradise At Siesta Key Vacation Home Rentals

Siesta Beach is regularly hailed on lists of the very best in the United States. It strings along Florida’s Treasure Coast, fringing the edge of Siesta Key like a wisp of white cloud that’s lapped by a sky-blue sea. But the sands aren’t the only draw. This barrier isle is also a fun-loving family hotspot, laden with coffee shops and oyster bars, kayak rentals and turtle sanctuaries. Siesta Key vacation rentals cover all sorts, whether you’re after a pad overlooking the waves of the Mexican Gulf or a modern apartment that takes the whole crew.

About Siesta Key Vacation Rentals

Siesta Key Dream Inn Vacation Rental – Sarasota, FL Siesta Key is the #1 Beach!!!

Siesta Key, a barrier island, is an exotic tourist destination in the state of Florida. It has pleasant weather, world-famous beaches and provides many fabulous opportunities to tourists such as dining, shopping and many sports activities. Presently, it has undergone renovations and come up with comfortable and enjoyable amenitiesa pedestrian esplanade, fascinating landscapes, tennis courts and picnic and playground areas, comfy accommodations etc. Thus, it has transformed into a paradisal spot. Tourists can rent various types of vacation home rentals in Siesta Keyvilla, cottage, condo,chalets and cabins.

Why Visit Siesta Key?

It really makes sense for tourists to visit Siesta Key, especially during the summer season. With a length of eight miles, it has brilliant quartz sand, turquoise waters, resorts and provides many beachside amenities to enable tourists to realize the idiom Variety is the spice of life.

Things to Visit in Siesta Key

Siesta Key is an amazing recreational island with lots of natural and man-made wonders that have made tourists go gaga over them. Those that every zealous tourist should include in his/her bucket list include the following:

Historic Spanish Point: This is a huge museum, spread over a 30-acre land. It is a good place for tourists to explore 5000-year-old history. It has colorful gardens, prehistoric mounds, pioneer-era buildings, nature trails, a large Butterfly garden and provides picnic facilities to tourists.

Beaches near Siesta Key

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Find Vacation Rentals In Or Near Siesta Key

Discover more than 2908 vacation rentals in Siesta Key that are perfect for your next trip. Whether you are traveling with a group, family, friends, or couples retreat in Siesta Key, RBO has all types of rental properties with top amenities, including indoor/outdoor/private swimming pools, Wi-Fi, hot tubs, self-catering, and more.

Rent By Owner offers vacation rentals near Siesta Key for all types of travelers, whether you are looking for a luxury home, villa, resort, condo, cabin, cottage, RV rental, or pet friendly accommodation in Siesta Key. Rent By Owner makes it easy to find and compare vacation rentals, matching you with rental properties from different vacation rental websites. By comparing these rental properties, RBO helps you find the best deals in Siesta Key. Luxury vacation rental prices start from $ 58 per night and affordable condos in Siesta Key start from $ 58 per night.

RBO offers a large selection of vacation rentals from top leading sites such as, Airbnb, VRBO,, RV Share, Outdoorsy, and many more providers. Filter your search dates and discover Siesta Key vacation homes for your next trip.

Weather For Siesta Key

With the fabulous weather patterns year-round, any time of the year is good a time to visit Siesta Key.

The hottest and the rainiest periods on Siesta Key are from June through August, but the rain is not usually an all-day event.

The coolest months are December through February with daytime highs in the 60’s F

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What To Do Near Siesta Key Vacation Rentals

Wobbling on a paddle board or blowing bubbles from a snorkeling tube, whizzing on personal watercraft or carving wakes through the Gulf all sorts of aqua fun is on the menu in Siesta Key. Home to boating outfitters, big fishing tourers, kitesurfing guides and turtle conservationists, this Floridian island is the place to be if you love making a splash. Dolphin cruises and whale spotting usually top the menu for families. A meeting with bottlenoses and beaked whales is all but guaranteed, between December and February.

Visit The Famous Beaches

Siesta Key Vacation Home Rentals by Owner

Beautiful Siesta Key Beach beckons. Dig your toes in the pristine white sand, splash in the waves, or collect some souvenirs to remember your stay. No matter what type of beach fun youre looking for, Siesta Key has it. And theres plenty to do beyond the beach such as shopping, top-rated dining, water recreation, fishing, boating, and plenty of other fun in nearby Sarasota.

When planning your next beach vacation, consider one of our Siesta Key condo vacation rentals. Bring the whole family, invite your friends, and treat everyone to a spacious townhome loaded with amenities like a private, heated pool. Browse the available options on this page and email or call us today if you have any questions. If youre convinced that a beautiful beachfront vacation is just what you need to unwind and rejuvenate, you can go ahead and book your condo right on our website whenever youre ready!

Learn more about our Siesta Key property management company.

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About Siesta Key Oceanfront Rental On Rent By Owner

With more than 472 oceanfront rentals in or near Siesta Key, Rent By Owner features many wonderful beachfront places to stay. Are you traveling with groups, families, friends, or as a couple to Siesta Key? RBO vacation homes will give you maximum comfort and essential amenities such as full kitchens, Wi-Fi, hot tubs, outdoor pools, recreation and theater rooms, laundry facilities, and more for your comfort.

Looking for a beach or oceanfront rental in Siesta Key with a pool? Rent By Owner has a large selection of villas, condos, cabins, and cottages. There are rentals for both large and small travel groups. RBO vacation homes can assist you in finding the perfect accommodation in Siesta Key that meets your travel budget, giving you the option to find direct access to the stunning beaches and ocean views, Rent by Owner has plenty of room for an extended family or small family, whether you are looking for a luxury villa, resort, furnished home, cozy condo with breathtaking views with private bedrooms and baths near Siesta Key, find an oceanfront rental with an amazing view.

Amenities That Exceed Your Expectations

Relax and come join us on Siesta Keys 99% pure quartz sandy shores. Rent Siesta Key is the quick, easy, and worry-free way to book your next Siesta Key Florida Vacation Rentals. Our properties are privately owned condominiums and vacation houses for rent scattered across the key, placing them in different desirable locations but always within walking distance to the beach. All of our Siesta Key vacation rentals are turn-key furnished with amenities that will meet and exceed your expectation. With our online reservation capabilities and available travel insurance, booking one of our Siesta Key rentals with Rent Siesta Key Florida is just as easy as booking a hotel. We have one of the largest inventories of places to rent on Siesta Key Beach. Book our Siesta Key Luxury Rentals today!

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Siesta Key Luxury Rental Properties

One sunset walk on the beach with the sugary sand passing through your toes and the sound of steel drums playing off in the distance, and you will realize why thousands call Siesta Key home. The water is warm, the sand is soft, and a cocktail isnt too far away. Come swim with the dolphins, sail a boat into the open sea, ride a bike along the water, or enjoy a night out in the Siesta Village. Find paradise on Siesta Key.

Siesta Key is an exceptional destination and thats why your experience here should be unparalleled. Stay in a vacation rental that reflects your refined tastes and discerning eye. Whether youre interested in an opulent condo rental near the beach or an expansive vacation home with stunning views, well help you find exactly what youre looking for. Your needs and preferences are paramount when it comes to providing a complete vacation experience for you.

Family Activities Near Siesta Key Vacation Rentals

Tiny vacation rental home by Siesta Key FL beach

Siesta Key is filled with unique attractions for kids of all ages. Vacation rentals are available near places like South Lido County Park, a waterfront park with swimming, kayaking, bird watching, and trails, and Turtle Beach, a sandy beach with a native population of sea turtles. Youll also like Livingstons Amusement Center, a colossal family-friendly activity space with go-karts, billiards, and games, as well as a bar for adults.

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Cheap Vacation Rentals In Siesta Key

Studio | 1 BA | Sleeps 2 |

Distance to beach: 0.3 miles to Siesta Key Beach access 10

  • Rentals by owner

About this property

*Calendar month rentals only*May – November – $1750 per month plus utilities May – November – $2000 per month plus utilities December – $2900 per month plus utilities January, February, and March – $4900 per month plus utilities April – $3900 per month plus …

Siesta Key Studio

“Siesta Dream”

My husband and I stayed at the garden Terrace studio. We loved our ultra clean, cozy & romantic little bungalow. It was perfect for us and our little 6 pound Chihuahua! Rich was so accessible, personable …

1 BR | 1 BA | Sleeps 3 |

Distance to beach: 0.5 miles to Siesta Key Main Beach

  • Rentals by owner

About this property

Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building – Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools , Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo, …

Siesta Key Condo

“6 mos getaway on Siesta Key”

Great location and amenities. Condo complex beachside. Shuttle to village, walk to beach and eateries. Sit by waterway and enjoy a cocktail. Socialize in the gym or at the pool. Friendly getaway.

1 BR | 1 BA | Sleeps 2 |

Distance to beach: 0.5 miles to Siesta Key Beach

  • Rentals by owner

About this property

Siesta Key Cottage

“Excellent pet-friendly bungalow”

1 BR | 1 BA | Sleeps 4 |

  • Pool



What Weather Can You Expect On Your Siesta Key Vacation

Come to your Siesta Key vacation rental during the summer to enjoy Siesta Keys warm yet temperate climate. May through September are the warmest months of the year, while Siesta Keys cold season goes from December until February. So if you want to get some sunbathing in, plan to come during the early to mid-summer months.

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How Can I Find A Vacation Rental Manager In Siesta Key

Find Rentals is the premiere guide for Vacation Rental Managers. We work with management companies from all over the worldto provide you with the most robust selection of professionally managed rentals. Use the search to access the selectionof management companies and rentals available.

Siesta Key is known throughout the world as one of the very best beaches for travelers to visit. Not just for the rich and famous, but for everyone to enjoy the super clean, incredibly soft sands and typically calm gentle Gulf Coast waters. Travelers from around the world flock to visit this gem along the Florida Gulf Coast. There is plenty of parking with public facilities and lots of room on the beach for all sorts of fun activites.

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Connect with a Manager in Siesta Key


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