Cottages Siesta Key

Updating...

age 0-16
565 Results

Relevance

Price: low to high

Price: high to low

Reviews

565 cottages

Luxury Beach Cotttage

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“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.

Match: Rental types Toaster

All filters match

Price per night from

$532

“Charming studio in lovely quiet neighborhood with fenced in private outside area.” This studio has everything you'll need. It's located in a beautiful neighborhood, great for walking. There's a small park just down the road a couple of blocks where you can sit and watch the amazing sun sets or just enjoy watching the boats ride by. The owners are very nice and have a few fur babies of their own, so they may allow you to bring your doggie,too! Sue/Dawn......thank you!!!! I hope to return & stay again.

Match: Rental types Toaster

All filters match

Price per night from

$229

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

Match: Rental types Toaster

All filters match

Price per night from

$132

These homes match some but not all of your filters. Clear all filters

Tiny House - Green Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$464

Tiny House - Blue Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$422

Tiny House - Margarita

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$470

Tiny House - Seashell

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$314

Tiny House - Flamingo

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$399

Tiny House - The Siesta

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$374

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$95

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$163

Casey Key 1-Bed Villa #2

Nokomis villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$172

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 57 minutes

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$194

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$447

SunWay Suites Unit 2 Plover

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$23

SunWay Suites Unit 4 Pelican

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$138

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$46

New York Avenue Rancher

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$445

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$138

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$489

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$489

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$489

Coastal Tiki 4/2 with outdoor paradise

Sarasota house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$457

SunWay Suites Unit 1 Sandpiper

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$149

House of Blues - Lovely 2-Bedroom Condo with Pool, W&D and Patio

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$201

Just a mile to downtown Sarasota!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$98

SunWay Suites Unit 3 Seagull

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$149

A Comfortable getaway!

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$115

Stay near the heart of Sarasota

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$115

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$290

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$305

Live Like a Local in the Heart of Sarasota!

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$251

The cozy hideaway!

North Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$182

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$659

Sarasota Rambler | Downtown MidMod Stay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$315

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.

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$103

Fishermans Cove FC Unit 205B *

Gulf Gate Estates condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$266

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Experience” This condo is well kept, clean and looks directly onto the Gulf of Mexico. We liked it because the furniture is up to date and replaced when it becomes worn. We also love the fact it is within walking distance of a good restaurant. In fact there is nothing about this rental that we don't like and that is why we return there year after year. A great choice for you to start a great experience!

1 of 2 match: Rental types, Toaster

1 of 2 filters match

Price per night from

$266

Viewing 38 of 565
rentals in Siesta Key

×

Also consider