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Check prices for these dates

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Aug 29 - Aug 31
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Sep 5 - Sep 7
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Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Apartments in Legacy Trail

Seabreeze at Anna Maria Island Inn
Exterior

Seabreeze at Anna Maria Island Inn

3.0 star property
9.0 out of 10, Wonderful, (32)
"Awesome place to stay "
The price is ￥40,957
￥51,835 total
includes taxes & fees
Sep 1 - Sep 2
Seabreeze at Anna Maria Island Inn
Pelican Post at Anna Maria Island Inn
Exterior

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (294)
"Place was very clean and perfect location for the beach/surrounding restaurants."
The price is ￥28,102
￥35,566 total
includes taxes & fees
Sep 1 - Sep 2
Pelican Post at Anna Maria Island Inn
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (319)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort
THE BEACH #107 Summer special 210 nite+fees Beachfront Full View
On the beach, sun loungers, beach towels

THE BEACH #107 Summer special 210 nite+fees Beachfront Full View

10.0 out of 10, Exceptional, (73)
"Our second time here and it was wonderful again. Annette is very sweet and the place is perfect!"
The price is ￥30,952
￥60,076 total
includes taxes & fees
Sep 4 - Sep 5
THE BEACH #107 Summer special 210 nite+fees Beachfront Full View
Casey Key Resort - Gulf Shores
Deluxe Studio, Bay View | View from room

Casey Key Resort - Gulf Shores

3.0 star property
8.4 out of 10, Very Good, (261)
"Cute place and property! Cozy, quiet and clean. The property manager was very nice. We enjoyed the private beach on the property. It is walking distance to 2 restaurants. Would def go back, we had a nice relaxing weekend. "
Casey Key Resort - Gulf Shores
Haley's at The Anna Maria Island Inn
Beach nearby, white sand, sun loungers, beach towels

Haley's at The Anna Maria Island Inn

3.0 star property
8.6 out of 10, Excellent, (373)
"It was a great stay"
Haley's at The Anna Maria Island Inn
Siesta Key Village-Suite #3: A Block to the Beach!
Beach nearby, sun loungers, beach towels

Siesta Key Village-Suite #3: A Block to the Beach!

9.4 out of 10, Exceptional, (51)
"Great little place in the middle of everything in Siesta Key Village. Within walking distance of beach, restaurant, drinks, ice cream and much more. Definitely recommend and will stay again!!"
The price is ￥21,855
￥51,075 total
includes taxes & fees
Aug 26 - Aug 27
Siesta Key Village-Suite #3: A Block to the Beach!
Premier Waterfront Room, Tiki Bar & Grill, Live Music, Pool, Gym, Kitchenette
Marina

Premier Waterfront Room, Tiki Bar & Grill, Live Music, Pool, Gym, Kitchenette

9.6 out of 10, Exceptional, (19)
"Loved the amenities "
Premier Waterfront Room, Tiki Bar & Grill, Live Music, Pool, Gym, Kitchenette
Charming Studio Unit Across from Lido Key Beach
Beach nearby, sun loungers, beach towels

Charming Studio Unit Across from Lido Key Beach

9.2 out of 10, Wonderful, (25)
"Perfect location for what we wanted. Everything was walkable, the property was quaint, and provided all the essentials for walking to the beach. A wagon, umbrellas, coolers, and chairs. "
Charming Studio Unit Across from Lido Key Beach
Steps to Siesta Key Beach / Charming 2-Bedr + den apartment with Patio & Pool
Fridge, microwave, oven, stovetop

Steps to Siesta Key Beach / Charming 2-Bedr + den apartment with Patio & Pool

9.4 out of 10, Exceptional, (62)
"We loved our weekend. The place was super clean and comfortable. We loved how close it was to the beach! Would come back!"
The price is ￥45,241
￥84,867 total
includes taxes & fees
Sep 2 - Sep 3
Steps to Siesta Key Beach / Charming 2-Bedr + den apartment with Patio & Pool
The Pink House Unit B: A Cozy Retreat Steps from the Beach
Iron/ironing board, WiFi, bed sheets

The Pink House Unit B: A Cozy Retreat Steps from the Beach

9.8 out of 10, Exceptional, (89)
"We loved this property, it was cute, cozy & extremely clean. We will definitely be back!!!"
The Pink House Unit B: A Cozy Retreat Steps from the Beach
Water Lovers Dream-2-bedroom 2 bathroom apartment with POOL 2 blocks from BEACH
Outdoor pool

Water Lovers Dream-2-bedroom 2 bathroom apartment with POOL 2 blocks from BEACH

10.0 out of 10, Exceptional, (13)
"We enjoyed and loved our stay here! The host, Stephan, was very helpful in furnishing what was needed and what we couldn’t get, we found nearby at the stores. The place was perfect for our family weekend getaway and we will definitely return soon. It was minutes from the beach and close to many restaurants. We definitely recommend it. "
Water Lovers Dream-2-bedroom 2 bathroom apartment with POOL 2 blocks from BEACH
Siesta Key Village-Suite #4: A block to the Beach!
Beach nearby, sun loungers, beach towels

Siesta Key Village-Suite #4: A block to the Beach!

9.2 out of 10, Wonderful, (32)
"Great location for anything you want to do in Siesta Key."
The price is ￥21,855
￥51,668 total
includes taxes & fees
Aug 24 - Aug 25
Siesta Key Village-Suite #4: A block to the Beach!
Cozy & peaceful 1 bedroom condo with a balcony a block from Lido Beach
Pool

Cozy & peaceful 1 bedroom condo with a balcony a block from Lido Beach

10.0 out of 10, Exceptional, (6)
"My Mom and I stayed for the weekend and had a great time. It is a quick walk to the beach and St Armand’s circle so you can park your car and walk everywhere. The owners do a great job keeping the locations clean and adding small amenities to make your trip nicer. It’s a great location for 2 people to enjoy the beach, but would be cramped if you had anymore."
Cozy & peaceful 1 bedroom condo with a balcony a block from Lido Beach
Palm Tree Villas
Beach nearby, white sand, beach umbrellas, beach towels

Palm Tree Villas

3.0 star property
9.2 out of 10, Wonderful, (169)
"Lovely property, clean and so close to the beach! Do need a car, for food/dinning. We'll be back."
Palm Tree Villas
Walk to Siesta Key Beach & Village | Private Patio | Prime Location!
Beach nearby

Walk to Siesta Key Beach & Village | Private Patio | Prime Location!

9.4 out of 10, Exceptional, (197)
"Very nice place good location within walking distance to just about everything clean and comfortable"
Walk to Siesta Key Beach & Village | Private Patio | Prime Location!
Coastal Getaway Retreat –Steps to the Beach! 2BR/1BA. Sleeps 4. In 4-Plex. Pool
Beach nearby, sun loungers, beach towels

Coastal Getaway Retreat –Steps to the Beach! 2BR/1BA. Sleeps 4. In 4-Plex. Pool

10.0 out of 10, Exceptional, (133)
"This is our 4th year staying here and we always enjoy our stay. We love the location!"
Coastal Getaway Retreat –Steps to the Beach! 2BR/1BA. Sleeps 4. In 4-Plex. Pool
KING STUDIO Pool Walk to Siesta key beach King bed DAILY RENTALS SPECAILS
Beach

KING STUDIO Pool Walk to Siesta key beach King bed DAILY RENTALS SPECAILS

9.6 out of 10, Exceptional, (30)
"Its a beautiful area, we enjoyed staying!"
The price is ￥19,013
￥36,661 total
includes taxes & fees
Sep 4 - Sep 5
KING STUDIO Pool Walk to Siesta key beach King bed DAILY RENTALS SPECAILS
Spacious beach cottage steps from the beach on Anna Maria Island
Beach nearby

Spacious beach cottage steps from the beach on Anna Maria Island

9.2 out of 10, Wonderful, (11)
"Rented a golf cart drove to several beaches. Will defenitely come again."
Spacious beach cottage steps from the beach on Anna Maria Island
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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Top Legacy Trail Hotel Reviews

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"We stayed here for 6 nights from August 16-22. It was everything and more! Single mom traveling with 16 year old twin boys was a new experience. We were upgraded upon check-in to a larger space where I had my own room! Tropical Breeze Resort provided everything we needed! So convenient to walk to restaurants and shops. Best part was the short walk to the beach. Met so many great people! "
Jennifer 6-night trip
Posted 4 hours ago
Tropical Breeze Resort