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Check prices for these dates

Compare 38 Cottages in Legacy Trail with updated reviews, rates, and availability.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (170)
"We were happy with everything!"
The price is SAR 1,832
SAR 2,210 total
includes taxes & fees
28 Feb - 1 Mar
The Inn On Siesta Key

The "Grouper"

9.6 out of 10, Exceptional, (10)
"I was very pleased with the final results after unfortunately getting double booked . The host was able to get us in their other property. Even though we had to change all our plans. We still ended up having a very comfortable and relaxing time. And was able to check out a little later. Very pleased with how they handled everything!!"
The price is SAR 371
SAR 791 total
includes taxes & fees
27 Feb - 28 Feb
The "Grouper"

Country Cottage Home

9.6 out of 10, Exceptional, (124)
"The house was as described, very quiet area. It was clean, the beds were comfortable, I would highly recommend to friends and families looking for a place in the area."
Country Cottage Home

NEW REMODEL 5 Min walk to Bch & Village, Private Pool, On the Canal 502-639-4259

9.8 out of 10, Exceptional, (15)
"The house had just been completely renovated due to the recent hurricane damage. Jim did an excellent job with everything to make sure our stay was top-notch. All the furnishings and appliances were brand new. We took the bikes out every day to Siesta Key Beach, which was just down the street. Absolutely amazing, and it took under 5 minutes! The rental location is very close (less than 1 mile) to fun restaurants in Siesta Key Village, with lot's of great bars and shopping. This place has it...
NEW REMODEL 5 Min walk to Bch & Village, Private Pool, On the Canal 502-639-4259

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (80)
"Amazing location of property, right on the beautiful beach. Plenty of parking, good restaurants nearby. We will be back "
The price is SAR 2,243
SAR 3,580 total
includes taxes & fees
23 Mar - 24 Mar
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (254)
"Always wonder what the placees lookes like veerry small but cute places . My only sugggestion, whhsjcj make at mosdtcprlces ie stay is a ccoi"
Charming cottage in quiet area, close to beach & bay.

Villa Mojito Dazzles

9.8 out of 10, Exceptional, (136)
"Amy was a wonderful host. She found a lovely place for us when Manasota Key was devastated by the hurricane. She and her team were great to work with and our stay was wonderful!"
Villa Mojito Dazzles

Castaway Cottage

10.0 out of 10, Exceptional, (3)
"The property was very easy to find and was everything we expected and more.comfy beds and a really nice pool/hot tub combo. Being Very close to beach access was nice nothing beats a 5 minute stroll to the ocean."
Castaway Cottage

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (317)
"Cute beach cottage across street from beach access. It is a little noisy as is right on beach drive but traffic died down by 10-11 pm. Place is equipped well. Only thing it didn't have that we would have used is a toaster. "
Across The Street From #1 Beach

Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach

10.0 out of 10, Exceptional, (18)
"Clean, well equipped condo with the beach for the back yard. Great location, close to Publix and local shops, restaurants and beaches, Tammy was welcoming and responsive."
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (112)
"We enjoyed our stay. It is perfect for families and the location is perfect!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

10.0 out of 10, Exceptional, (1)
"Great Vacation! Very clean and everything you needed. Name “solitude” is appropriate. Nice quiet getaway from hustle and bustle of spring break crowd. Lisa the property manager was very nice and accommodating."
The price is SAR 1,313
SAR 2,127 total
includes taxes & fees
2 Mar - 3 Mar
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Cozy Cottage - Minutes from Beaches and Historic Dearborn St!

10.0 out of 10, Exceptional, (8)
"Well maintained, quiet, cute little place, comfortable. Hosts are very good communicators"
The price is SAR 476
SAR 975 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Cottage - Minutes from Beaches and Historic Dearborn St!

Cozy, family/pet friendly less than a block to white sandy beaches. Trolley stop

8.0 out of 10, Very Good, (1)
"Pros of this rental: the location to the beach which was less than 2 blocks away, easy off street parking, dog friendly, beach chairs, umbrella and toys for our use. The place is the right size for a couple or a small family. Cons: no dishwasher & the couch had a couple of large stains on them from previous renters, we covered them with sheets and notified the rental company"
Cozy, family/pet friendly less than a block to white sandy beaches. Trolley stop

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

9.6 out of 10, Exceptional, (109)
"Great little cottage with amazing views, warm and welcoming place to stay! Owner was responsive and wonderful to work with, super flexible letting us get a golf cart dropped off before checkin and was great to work with. Great vacation in the beautiful quiet part of AMI!"
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Bradenton Cottage w/ Screened Pool: 12 Mi to Beach

8.8 out of 10, Excellent, (10)
"Was down for National Soccer showcase at Lakewood Ranch. Good location close by and spacious "
Bradenton Cottage w/ Screened Pool: 12 Mi to Beach

Villa Margarita Sparkles

9.8 out of 10, Exceptional, (136)
"We loved this property/location. Unfortunately we had to leave a day early due to Helene. The owner was very concerned about this and offered to refund us the day we missed. I would definitely stay here again. "
Villa Margarita Sparkles

Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1

10.0 out of 10, Exceptional, (85)
"My wife and i had a great weekend in Alice's cottage..Pkace was clean and clearly well maintained. Oh and did i mention only a few steps to a white, soft sandy beach? Yes this was a great old Florida' experience. Not many of these gems left"
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1

Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...

9.6 out of 10, Exceptional, (40)
"The property was as described and absolutely amazing! It was beautiful inside, beds were comfortable, living area had comfortable furniture. Amenities were excellent. Not a bad thing to say about this place. Easy check in/out. Will definitely stay there again! "
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (50)
"This place was exactly as described. Cute little cottage with an ocean view. We loved waking up to hearing the ocean and watching the dolphins pass through every day. Beach is loaded with beautiful shells. We had a maintenance issue but the owner was extremely helpful had it taken care immediately "
The price is SAR 1,868
SAR 3,207 total
includes taxes & fees
26 Feb - 27 Feb
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Legacy Trail

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4559)
"property was well kept and room was clean"
The price is SAR 960
SAR 1,169 total
includes taxes & fees
24 Feb - 25 Feb
Tropical Beach Resorts

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (188)
"All stay was friendly, very clean. Rooms cleaned daily. Would rate 5 "
The price is SAR 2,673
SAR 3,382 total
includes taxes & fees
23 Feb - 24 Feb
Anna Maria Beach Resort

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (215)
"Nice little spot close to Siesta Key Beach.Even has an outdoor stage.I like entertaining and it looks like a perfect place to practice.i really did not mind being in the Tiny House it kind of felt like a Hollywood prop.Anyway this is Hollywood and you are in my world.Love is everything."
The price is SAR 495
SAR 771 total
includes taxes & fees
10 Mar - 11 Mar
Tiny House Siesta
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.