Beach Rentals & Vacation Rentals in Siesta Key

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Wireless Internet
Air conditioning
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Private indoor pool
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DVD player
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Cot available
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Shared outdoor pool (heated)
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Shared indoor pool
Private outdoor pool (heated)
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Pool or snooker table
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Fax machine
Linen provided
Iron
Hair dryer
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Towels provided
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Bicycles available
Climbing frame
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Private fishing lake or river
Staffed property
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Housekeeping Included

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Parking
Car not required
Children under 5
Smoking allowed

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Beach or lakeside relaxation
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Golf course on site or within 15 min walk
Golf within 30mins drive
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37 beach rentals

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Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 1 minutes

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$266

Siesta Key private beach access

Siesta Key villa

3 bedrooms
3 bathrooms

sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

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$509

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.

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$514

Midnight Cove #532 in Siesta Key, FL- Sun, Sand & Save 7.5% to 22.5% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

“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

Midnight Cove #714 in Siesta Key, FL- Sun, Sand & Save 7.5% to 22.5% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

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$144

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & Save 10% to 25% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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$284

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.

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$602

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

2 bedrooms
4 bathrooms

sleeps 6

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$430

Great rentals within 20 miles that match your search

ZILLI VILLA

Longboat Key villa

2 bedrooms
2 bathrooms

sleeps 10

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$487

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

1 bedroom
1 bathroom

sleeps 4

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$482

Charming Private Studio in Historic Downtown Area

Sarasota studio

Studio
1 bathroom

sleeps 3

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$258

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

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 4

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$161

Great Location and Best Price in Sarasota

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

Responds fast! avg. 1 hour 46 minutes

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$92

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

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$234

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

Vacation Home on Alligator Drive . Winter 2025 Special !

Venice house

3 bedrooms
2 bathrooms

sleeps 5

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$149

Clean comfort in Sarasota-book now for comfort

Sarasota caravan/mobile home

1 bedroom
2 bathrooms

sleeps 4

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$134

Cute Efficiency Apartment - nice neighborhood

Sarasota apartment

1 bedroom
1 bathroom

sleeps 2

“Great place to stay in sarasota” Very nice one bedroom apartment with everything you need. Close to everything. Quiet neighborhood. Just a great piece of mind renting from Terry had no worries at all.

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$103