Siesta Key Vacation Rentals

Beachfront condo on Siesta Key
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
Updated beachfront condo directly on the sands of Turtle beach
From $1,195 /Week
SIESTA KEY CONDO-DIRECT OCEAN FRONT, 8TH FLOOR, LUXURY, SPACIOUS, BEST VIEW
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 4
2 bedroom, 2 bath, 8th floor, beautiful furniture and accessories, 30 foot lanai, condo directly overlooks/faces the ocean and beach. Min 2 weeks stay required.
From $1,350 /Week
Enjoy Stunning Sunsets at this Luxurious Gulf Front Condo on Siesta Key
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
Min - 2 Week Rentals - Crystal Sands Siesta Key Unit 502 - Song of the Sea, where Luxury meets Paradise
From $229 /Night
Tranquil Oasis Located on World Class Midnight Key
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
Enjoy the best of both worlds during your Florida vacation in this cozy, tranquil, affordable oasis located on beautiful Siesta Key.
From $905 /Week
Sarasota-Siesta Key Coastal Five Bedroom Home with Pool and Spa and steps to the beach.
South West FL > Siesta Key
Condo , Bedroom(s): 5 , Sleeps: 13
Sold, no longer available for rental, see 1046. 5 Bedroom Pool House Rental steps to Siesta Beach!
From $3,925 /Week
Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach
South West FL > Siesta Key
House , Bedroom(s): 4 , Sleeps: 12
4 Bedroom House Rental in Siesta Key
From $575 /Night
Couples and Family Friendly. Some pet friendly units are available too.
South West FL > Siesta Key
Condo , Bedroom(s): 1 , Sleeps: 4
siesta key condo rental
From $199 /Night
Siesta Key Beachfront 3 Bedroom Private Home
South West FL > Siesta Key
House , Bedroom(s): 3 , Sleeps: 7
Siesta Key House Rental
From $395 /Night
Comfortable, cozy home with spacious pool area in walking distance to the beach
South West FL > Siesta Key
House , Bedroom(s): 3 , Sleeps: 6
Siesta Key House With Dock!! 3 bedrooms, 3 bathrooms, heated pool, walking distance to Siesta Beach
From $1,700 /Week
Exclusive!  #1 USA Beach Siesta Key,.(HOUSE)
OFFER
Exclusive! #1 USA Beach Siesta Key,.(HOUSE)
South West FL > Siesta Key
House , Bedroom(s): 2 , Sleeps: 4
E-Z BEACH ACCESS, Top World Beach #1-USA BEACH SIESTA KEY, FL. 2-minutes from the Award-winning beach and village, and no parking-lot traffic getting there.
From $1,285 /Week

OFFER BOOK THESE DEALS IN ADVANCE 2021-22 Siesta Key Beach, FL. PRIVATE ISLAND HOUSE

Special offer period: Jan 4, 2021 - Mar 31, 2022

Extraordinary Key West style 3 Bedroom 3.5 Bath pool home on the Grand Canal!
South West FL > Siesta Key
House , Bedroom(s): 3 , Sleeps: 6
3 Bedroom 3.5 Bath Siesta Key Pool Home on the Grand Canal 1 bridge from Robert's Bay
From $400 /Night
Bellevue-Siesta
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 4
Spacious luxury end unit 2BD 2BA
From $1,098 /Week
Siesta Key with private beach with complimentary lounges and umbrellas!
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
2 BR, 2 Bath condominium in beautiful Siesta Key, a barrier island in Sarasota.
Sandy's Siesta Key Condo
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 4
We are located in Midnight Cove 1 in Siesta Key, Fl. Luxury accommodations at an affordable price!! Pay no service fees when booking directly with me!!
From $140 /Night
Luxury 2400 sq ft 6th floor condo with private access to Crescent Beach
OFFER
Luxury 2400 sq ft 6th floor condo with private access to Crescent Beach
South West FL > Siesta Key
Condo , Bedroom(s): 3 , Sleeps: 6
Large open floor plan is great for family vacations. Location...Location...Location !! Everything is within walking distance.
From $251 /Night

OFFER 10% DISCOUNT OFFERED FOR BOOKINGS MADE LESS THAN 30 DAYS PRIOR TO ARRIVAL.

Special offer period: Jan 1, 2021 - Dec 31, 2021

House of the Sun Unit 402
OFFER
House of the Sun Unit 402
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
Beachfront Siesta Key, Florida Condo Rental- This is a 2 bedrooms, 2 baths beachfront unit on Crescent Beach.
From $179 /Night

OFFER Call for discount pricing.

Special offer period: Dec 1, 2020 - Dec 31, 2021

The Bella Siesta: Walking distance to Siesta Village; 5 minutes to Siesta Key Beach
South West FL > Siesta Key
House , Bedroom(s): 3 , Sleeps: 8
Renovated 3 bedroom, 2 bathroom home with new saltwater pool built in 2019.
From $450 /Night
Spacious waterfront Villa with gorgeous views, 1 mile to Siesta Beach
South West FL > Sarasota
House , Bedroom(s): 4 , Sleeps: 6
4 bedrooms, 3 baths, Pool, one mile to Siesta Beach, sleeps 6 pers.
From $1,800 /Week
Beautiful lake front home with Pool in close distance to Siesta Key Beach
South West FL > Sarasota
House , Bedroom(s): 2 , Sleeps: 4
2 Bedrooms, 2 Bathrooms, heated Pool, sleeps 4 Persons, 3 miles from Siesta Key
From $1,050 /Week
LOCATION SIESTA & DT SARASOTA Coastal Elegant House West of the Trail Family Fun
South West FL > Sarasota
House , Bedroom(s): 3 , Sleeps: 6
Spacious coastal/elegance Fully equipped a perfect place for you and your family. Southside Village, Siesta Key, Downtown, & St Armands Circle.
From $245 /Night
Sarasota Awaits You - Available Dec 15 - 31, 2021,  and  May & June 2022
OFFER
Sarasota Awaits You - Available Dec 15 - 31, 2021, and May & June 2022
South West FL > Bradenton
Mobile Home , Bedroom(s): 2 , Sleeps: 4
A newly renovated home awaits those who love resort life, want to explore Sarasota, and can chill out in their own private property. Budget Friendly!
From $100 /Night

OFFER Dec - $1,000.00 for Dec 15 to 31, 2021 May - $1,600.00 June- $1,600.00

Special offer period: Jun 12, 2021 - Mar 31, 2022

Fishermans Cove A102 - On Turtle Beach on Siesta Key
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
Fishermans Cove A102 - On Turtle Beach on Siesta Key
From $332 /Night
Fishermans Cove A302
South West FL > Siesta Key
Condo , Bedroom(s): 2 , Sleeps: 6
2 Bedroom condo rental in Siesta Key
From $1,150 /Week
Gorgeous newly remodeled pool home on St. Armand's Circle for 8
South West FL > Sarasota
House , Bedroom(s): 4 , Sleeps: 8
125S - 4 Bedrooms, 4.5 Baths (Sleeps 8)
From $650 /Night
Fabulous refurbished coastal pool home on Lido Key seconds from St. Armand's Circle
South West FL > Sarasota
House , Bedroom(s): 3 , Sleeps: 8
3 Bedroom 3.5 Bath, Sleeps 6 in beds, and 2 more on a pull-out sofa
From $695 /Night

Is Siesta Key, Florida a Good Place to Visit?  

About Siesta Key, Florida

Situated on the Southwest Gulf coast south of Clearwater Beach, Siesta Key is a barrier island just off the mainland city of Sarasota and attracts visitors to its world-class beach. 

Siesta Key Beach was twice named the nation's best beach with 8-miles of brilliant quartz sand and turquoise waterfront. For such a small area, this little Key is big on shopping, dining, and nightlife with waterfront amenities. Whether you're looking for a fun vacation with the kids or a romantic trip for two, Siesta Key offers something for everyone.

Siesta Key hosts a variety of festivals and events year-round like the unique Chalk Festival with 3D pavement artwork delighting visitors. There is also a Siesta Beach Seafood and Music Festival, Sand Sculpting Festival, and more that draw visitors to relax and enjoy the fun in spacious rentals. Siesta Key owners are proud of their waterfront homes and offer beautiful vacation rentals to visitors looking to enjoy what Siesta Key has to offer.

What Beaches are found on Siesta Key, Florida?  


Siesta Key

Siesta Key is a barrier island located in Sarasota County, Florida with a population hovering around 6,500 people, although many “snowbirds” come to escape the winter months and create a spike in seasonal population. Famous for its white sandy beaches that stay cool to the touch, Siesta Key is also home to water recreation like kayaking and boating and attracts relaxation and adventure seekers alike. And after $21 million in renovations to public facilities including a pedestrian esplanade, lounging at Siesta Key feels like relaxing at a resort.  

Siesta Key Beach

The main draw to Siesta Key is Siesta Key Beach with its dazzling white, quartz sand, and beachfront amenities. Come and lounge or spend the day strolling along the barrier island. Award winner for many years in a row as one of America's best beaches to experience, with that many awards you know it has to be great.

Crescent Beach

Located south of Sarasota Beach, Crescent Beach provides a sense of privacy and seclusion among its waterfront condos and hotels. Crescent Beach has more limited access than Siesta Key Beach but also tends to draw fewer crowds. Much of Crescent Beach is private, though there is a tranquil strip of beachfront accessible by a small parking area for visitors.

Turtle Beach

Animal lovers hoping to get a glimpse of Florida's migrating sea turtles head to Turtle Beach to see its thriving population nesting on the shore. From May 1 to October 31, the sea turtles flock to Florida's Gulf Coast to nest and make their home right on Siesta Key. With 2,6000 feet of beachfront, visitors can come to Turtle Beach to play, have a picnic, or enjoy the children's play area.

What are Popular Things to Do at Siesta Key, Florida?

Highlights of Siesta Key, Florida

  • There are three powdery white beaches on Siesta Key made from quartz white sand that stays cool to the touch. There’s something for everyone whether you want to relax or go kayaking in the Gulf of Mexico.
  • The Siesta Key Beach area recently underwent a $21 million renovation including an esplanade to stroll.
  • Hundreds of sea turtles return to nest each year at Turtle Beach
  • Best Suited for beach lovers and anyone looking for a relaxing vacation whether families or couples on a romantic getaway.

Things to do in Siesta Key, Florida

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.

  • Three major breathtaking beaches - Siesta Key Beach, Crescent 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
  • Kayaking
  • Fishing
  • SUP boarding
  • Kiteboarding
  • Jet-skiing
  • Biking
  • Parasailing
  • Scuba diving
  • Skimboarding
  • Bodyboarding
  • Eco-Tours
  • Boutique shopping
  • Fine dining and casual restaurants

Siesta Key, Florida FAQ's

What types of property can I rent on Siesta Key, Florida?

Florida Rental By Owners (FLARBO) is full of a wide variety of vacation rentals in Siesta Key, Florida including condos, cottages, town-homes, duplexes, villas, holiday, and private homes. Our 2019 property selection features several homes and condos in Siesta Key. We recommend selecting a property based on your needs such as proximity to beach areas, waterfront docks, parking, wheelchair accessible, nearby attractions, and whether or not the property is pet-friendly or boat-friendly.

Should I rent a Cottage on Siesta Key?

Yes, if a cottage is right for you! Most cottages in Siesta Key offer amazing beachfront views! Some include free beach gear and many amenities such as pools, hot tubs, backyard beaches, tiki huts, fitness rooms, and ping pong tables. If this is what you are looking for, then you should rent a cottage in Siesta Key.

Should I rent a Condo on Siesta Key?

Absolutely! Siesta Key accommodations include condos which often offer unique amenities and the perfect space rather than a Siesta Key cottage or sizeable private home for example. House rentals are usually great for family vacations, larger groups or those who prefer having an entire house and outdoor property to themselves.

Can I rent a pet-friendly rental on Siesta Key?

Yes, we have a lovely selection of pet-friendly rentals in our Siesta Key inventory of homes.  We love our pets, and we are sure you do too! FLARBO.com has many pet-friendly rentals on Siesta Key. You can use our search feature to narrow down our Siesta Key rental properties to show those that are pet-friendly.

Can I rent a boat-friendly rental on Siesta Key?

Siesta Key is the perfect place to bring your boat or rent one from a local vendor! FLARBO.com (Florida Rental By Owners) has many boat-friendly vacation rentals with docks on Siesta Key. Use our search filters to narrow down our Siesta Key rental properties to show those that are boat-friendly .

Is Siesta Key a good place for Snowbirds looking for monthly rentals?

Yes, there are many homes and condos that rent on a monthly basis on and near Siesta Key, Florida that are perfect for longer stay guests. Don't forget to search for more options just off the island in nearby culture-rich Sarasota.


Read more