Cottages Siesta Key

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103 cottages

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$745

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Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$193

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$295

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

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$95

Beachfront view, toes in the sand and gulf. Simply paradise, book now your beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 16 minutes

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$275

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$229

Efficiency Unit for Snowbirds in Venice, Florida

Venice studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

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$103

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$409

Beautiful Home Near Many Golf Courses in LWR/Sarasota, FL.

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$100

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$716

Condo w/Private Beach, WiFi/Cable, Fishing Pier, W/D, Stairs to Unit

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 4 minutes

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$139

Responds fast! avg. 3 hours 41 minutes

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$161

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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$999

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$115

Perfect vacation spot

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Good location. Nice host.” Location to near by beaches and downtown were just perfect. It was comfortable and had all we needed for our visit with a lovely host. Definitely would stay here again if we visit Sarasota again.

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$155

Tara Golf & Country Club Condo

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

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$144

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

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$144

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$144

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$161

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$454

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$337

Five star Downtown Sarasota tropical garden Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Paradise Found in Downtown Sarasota” Absolutely charming, fully redone/ upgraded bungalow close to everything Sarasota has to offer. This was the third year running my wife & I have stayed at the wonderful home located minutes from Sarasota's best beaches, restaurants & shopping. We fully intend to return again next year! The two bedroom home is in pristine condition. Beautifully decorated, lovely hardwood flooring throughout with a fully stocked (appliances, crockery, pots/pans, cutlery, etc...) kitchen & renovated bathroom. Everything you need is provided, just arrive & settle-in. A huge projection screen in the living room, should you want to have an at-home movie night (rental Dvd's a 5-minute walk away @ Publix). There's also a regular flat-screen TV in the living room, as well as a wall-mounted TV in the bedroom. The backyard is, personally, my favourite part of the home. A screen-in lanai to eat in & a beautifully manicured backyard to relax in under the tiki hut or under the palm trees. There are a few seating areas throughout the backyard. Find the space you like the best, sit-back & relax with a cool cocktail- very civilized & very beautiful. You'll feel like you're in the Caribbean, not Florida in this backyard. Maureen & Pat, your hosts who, very conveniently, live right next door have provided everything you need, including all the beach chairs, umbrellas, beach towels, etc...to take along with you to Sarasota's beautiful beaches. Maureen has also provided tons of literature about the area in the house- restaurant menus, local mags, maps- everything. Maureen & Pat are always happy to suggest restaurants, beaches, shopping, golf, etc. They know Sarasota well, are friendly & happy to help in any way they can to ensure you have a wonderful stay. My wife & I can honestly say we love this property, have encountered no negatives about the place in three years of week-long stays & look-forward to our time there each year. We recommend this lovely home to everyone.

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$189

Excellent Location - Gulf/Beach View - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 38 minutes

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$344

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!

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$184

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♡

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$258

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 14 minutes

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$224

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 22 minutes

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$196

2 bdrm Condo Villa in Birds Bay venice, florida

Venice villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$161

Venice Island on BEACH 8th flr near Siesta Key

Venice apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$241

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

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$258

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.

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$165

Walk to Nokomis Beach

Nokomis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$148

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.

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$314

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

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$271

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$101

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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$401

Luxury accommodation in Venetia, 3 months stay

Venice house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$192

Lovely 3 BR Home with Office & Heated Pool at Tara

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$166

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