Updating...
Responds fast! avg. 2 hours 3 minutes
Price per night from
$258
Great rentals within 20 miles that match your search
AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS
Bradenton Beach apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Responds fast! avg. 3 hours 22 minutes
Price per night from
$197
Responds fast! avg. 1 hour 15 minutes
Price per night from
$461
Price per night from
$173
Price per night from
$153
“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!
Responds fast! avg. 3 hours 50 minutes
Price per night from
$806
Price per night from
$161
Price per night from
$138
Grand accomdation on USA #1 Beach - Siesta Key Fl
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Price per night from
$206
Price per night from
$242
Responds fast! avg. 2 hours 40 minutes
Price per night from
$259
Price per night from
$411
Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.
Price per night from
$142
Vacation Home on Alligator Drive . Winter 2025 Special !
Venice house
- 3 bedrooms
- 2 bathrooms
- sleeps 5
Price per night from
$138
Siesta Tropical Retreat: Modern 3 Bedroom Pool Home in Siesta Key Village
Siesta Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 9
“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!
Price per night from
$402
4 Bedroom with Gulf View Siesta Key FL Beach Fun
Siesta Key apartment
- 4 bedrooms
- 4 bathrooms
- sleeps 10
“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.
Price per night from
$517
Responds fast! avg. 1 hour 0 minutes
Price per night from
$207
SNOWBIRDS 25 - 40% OFF 5* Waterfront Canal Pool Home-Dock/Kayak/Bikes/Family fun
Holmes Beach house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$230
“Home away From Home” I've been staying at the Graham's condo once or twice a year for the last 9 years or more. It's always been pristine clean. Accomodations are the best. Rooms large and bright and fully equipped. Decor is so welcoming. Location is the best. Only decisions to make are beach or pool, and where to eat tonight! I consider it my "home away from home." You won't be disappointed, and the value cannot be beat. Don't hesitate to book your reservation.
Price per night from
$173
Clean comfort in Sarasota-book now for comfort
Sarasota caravan/mobile home
- 1 bedroom
- 2 bathrooms
- sleeps 4
Price per night from
$135
Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.
Price per night from
$316
Responds fast! avg. 1 hour 37 minutes
Price per night from
$312
Price per night from
$143
Chinaberry 474 at Midnight Cove Siesta Key, FL.
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$266
Newly discounted rates! Gorgeous one bedroom across from beach, near village!
Siesta Key condo
- 1 bedroom
- 1 bathroom
- sleeps 3
“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA
Price per night from
$247
“Location location” Great house convincent , clean , close to everything
Price per night from
$129
“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...
Price per night from
$432
Price per night from
$228
Chinaberry 932 at Midnight Cove Siesta Key, FL.
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$172
Responds fast! avg. 2 hours 27 minutes
Price per night from
$140
Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.
Price per night from
$190
Steps to beach and bay on beautiful Anna Maria Island
Bradenton Beach apartment
- 2 bedrooms
- 1 bathroom
- sleeps 5
Price per night from
$102
STUNNING Direct Beach&Gulf Front 2 Bedroom Condo on Siesta Key, Amazing views!
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 46 minutes
Price per night from
$263
Price per night from
$365
BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY
Bradenton house
- 3 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$369
Pool & Hot Tub-Pine Bay Forest 3-Bedroom Condo, Near AMI Beaches 3 month min
Bradenton condo
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$107
Price per night from
$167
Price per night from
$190