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Price: high to low
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Price per night from
$234
Price per night from
$276
Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key
Osprey cottage
2 bedrooms / 1 bathroom / sleeps 2
Price per night from
$132
WATERFRONT SARASOTA COUNTY, CASEY KEY. 5 MILES TO SIESTA KEY BEACH. POOL HOT TUB
Osprey houseboat
3 bedrooms / 1 bathroom / sleeps 11
Price per night from
$435
PIRATE'S TREASURE WATERFRONT HOUSEBOAT/TINY HOUSE/FLOATING HOME
Osprey houseboat
1 bedroom / 1 bathroom / sleeps 7
Price per night from
$274
Price per night from
$630
Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key
Osprey condo
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$81
Gorgeous Updated Heated Saltwater Pool Home, WiFi, Dog Friendly, Kayak Launch &
Osprey house
3 bedrooms / 4 bathrooms / sleeps 8
Responds fast! avg. 3 minutes
Price per night from
$261
Great rentals within 20 miles that match your search
Siesta Key - 2bdrm on the beach - amazing views!!
Siesta Key condo
2 bedrooms / 2 bathrooms / sleeps 5
“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.
Responds fast! avg. 2 hours 16 minutes
Price per night from
$394
Responds fast! avg. 2 hours 47 minutes
Price per night from
$105
Responds fast! avg. 2 hours 14 minutes
Price per night from
$179
Price per night from
$85
“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.
Responds fast! avg. 2 hours 18 minutes
Price per night from
$188
“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.
Responds fast! avg. 3 hours 11 minutes
Price per night from
$386
Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck
Sarasota apartment
2 bedrooms / 2 bathrooms / sleeps 4
“Very comfortable lodgings” Loads of extras in this unit. Well cared for, updated very nicely. Disappointed that the large deck was taken out of service, possibly for a year! It seems to me that usage could have been sustained by posting signs that caution all users to wear appropriate foot-ware on the deck at all times, and to avoid running or playing on the deck. Also the deck restoration could be tackled section by section so as to retain the use by all tenants and owners.
Responds fast! avg. 3 hours 25 minutes
Price per night from
$269
Responds fast! avg. 2 hours 27 minutes
Price per night from
$342
“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!
Responds fast! avg. 1 hour 25 minutes
Price per night from
$220
Luxury Romantic Oceanfront Siesta Beach Condo #304
Siesta Key apartment
1 bedroom / 1 bathroom / sleeps 4
“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!
Responds fast! avg. 2 hours 9 minutes
Price per night from
$188
Responds fast! avg. 1 hour 13 minutes
Price per night from
$133
“beautiful, relaxing vacation!” Beautiful home with all the amenities a family would need. Enjoyed the open kitchen, dining area. The two bedrooms were very comfortable each with their own baths. So close to the beaches, canal and lovely town of Venice.
Price per night from
$100
2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!
Siesta Key apartment
2 bedrooms / 1 bathroom / sleeps 5
“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡
Responds fast! avg. 1 hour 34 minutes
Price per night from
$243
“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!
Price per night from
$772
Price per night from
$138
Responds fast! avg. 1 hour 23 minutes
Price per night from
$89
Grand accomdation on USA #1 Beach - Siesta Key Fl
Siesta Key apartment
2 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$121
Price per night from
$191
Responds fast! avg. 1 hour 51 minutes
Price per night from
$198
Price per night from
$315
Luxurious 2 BR Condo - Short Walk to Siesta Beach, #1 in The USA
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
$150
Beautiful Home Near Many Golf Courses in LWR/Sarasota, FL.
Lakewood Ranch apartment
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$96
Sarasota 2BR 2BTH Condo Close to Siesta Key Beach
Sarasota apartment
2 bedrooms / 2 bathrooms / sleeps 4
Responds fast! avg. 1 hour 17 minutes
Price per night from
$10
Private Heated Pool Home. Walk or bike to Shamrock Park and close to the beaches
Venice house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$254
Price per night from
$176
Charming Lido Key Beach House 5 min Walk to Beach!
Sarasota house
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$394
Secluded Cottage on 6 Acres IN TOWN 10min to Beach
Sarasota house
2 bedrooms / 1 bathroom / sleeps 5
Responds fast! avg. 2 hours 1 minutes
Price per night from
$171
~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO
Longboat Key studio
Studio / 1 bathroom / sleeps 3
“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.
Responds fast! avg. 2 hours 25 minutes
Price per night from
$154