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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Browse Select Legacy Trail Apartments

The Ringling Beach House
Aerial view

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (300)
"We enjoyed our stay. The location was great. It was a 5 min walk to the beach, and a 5 minute walk to all the restaurants. Would definitely recommend. "
The Ringling Beach House
Pelican Post at Anna Maria Island Inn
Garden

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (267)
"Beautiful boutique resort. Clean rooms, great pool and hot tub. Walking distance around Anna Maria Island. Parking included. I highly recommend :)"
The price is CA $407
CA $515 total
includes taxes & fees
Apr 29 - Apr 30
Pelican Post at Anna Maria Island Inn
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, (302)
"I love that this property is right on the beach. We were there over Christmas. The property was not fully booked, so it was fairly quiet. The Gulf was too cold for us, but we enjoyed using the the provided lounge chairs to relax on the beach. Lots of shelling to do. Not a lot of people at this time. Pool was not a bad temperature and was clean. The property looks like an old motor lodge, but they have kept it nice. Our room did not have a lot of updates, but it was sufficient. A roll of paper...
Sea Club I Beach Resort
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!

9.2 out of 10, Wonderful, (44)
"Perfect spot and nice place! Very easy walk everywhere! No need for a car! Definitely would recommend to anyone!!!The only negative thing was how late check in was & how early checkout was. Just be prepared!"
Siesta Key Village-Suite #3: A Block to the Beach!
Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking
Beach nearby

Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking

8.6 out of 10, Excellent, (59)
"Perfect little place for a couple! "
Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking
Charming Studio Unit Across from Lido Key Beach
Beach nearby, sun loungers, beach towels

Charming Studio Unit Across from Lido Key Beach

9.0 out of 10, Wonderful, (14)
"The place was amazing!!! Clean,safe,comfortable great location!!! It had beach chairs and a cooler and umbrella towels!!! I had an amazing stay!!!! Thanks ago!!!"
Charming Studio Unit Across from Lido Key Beach
Beachside Studio Located Across from Main Beach and Half Mile to Village
Property grounds

Beachside Studio Located Across from Main Beach and Half Mile to Village

8.8 out of 10, Excellent, (149)
"Place was clean & comfortable, bathroom a little small"
The price is CA $157
CA $466 total
includes taxes & fees
Apr 30 - May 1
Beachside Studio Located Across from Main Beach and Half Mile to Village
COZY STUDIO APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! KING BED. SLEEPS 2.
Terrace/patio

COZY STUDIO APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! KING BED. SLEEPS 2.

10.0 out of 10, Exceptional, (135)
"Great location on AMI. We were in the studio unit 3 and loved being able to step outside our door to the pool. There are nice 4 person tables with umbrellas as well as lounge chairs. Pool was nice and warm. Nice beach towels provided and available chairs for the beach were no problem at all. Grill worked great and was fun to have by the pool. Loved being so close to the beach as well. The keypad for entry was nice and easy for coming and going, as well as check in and check out. Jill...
COZY STUDIO APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! KING BED. SLEEPS 2.
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
Outdoor dining

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

10.0 out of 10, Exceptional, (51)
"We enjoyed staying here. It was very clean and had everything you needed. It's close to the beach. I would recommend this place. "
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
Steps to Siesta Key BEACH! Pool, Tennis Court, Shuffle Board, Basketball!
Fridge, microwave, oven, stovetop

Steps to Siesta Key BEACH! Pool, Tennis Court, Shuffle Board, Basketball!

10.0 out of 10, Exceptional, (39)
"I had an absolutely incredible stay at this beachfront accomodation! The location couldn’t be more perfect—just steps away from the ocean.The home itself is packed with thoughtful features and amenities. The kitchen was fully stocked with everything we needed to cook (and then some!), including a blender, coffee maker, and spices. The living space was bright, airy, and tastefully decorated with beachy vibes throughout. The host was incredibly responsive and kind. We will definitely return"
Steps to Siesta Key BEACH! Pool, Tennis Court, Shuffle Board, Basketball!
Villa in Osprey that sleeps the whole family
Outdoor dining

Villa in Osprey that sleeps the whole family

9.8 out of 10, Exceptional, (30)
"Great stay! The place was clean and roomy. Tucked back in a quiet area and close to the beach. I would 100% come back!"
Villa in Osprey that sleeps the whole family
Siesta Cooler: Only Minutes Walk to Siesta Beach!
Beach nearby

Siesta Cooler: Only Minutes Walk to Siesta Beach!

9.6 out of 10, Exceptional, (45)
"Nice property. In the middle of everything."
The price is CA $270
CA $585 total
includes taxes & fees
May 18 - May 19
Siesta Cooler: Only Minutes Walk to Siesta Beach!
Tiny House Calypso with 1st floor sleeping
2 bedrooms, WiFi, bed sheets

Tiny House Calypso with 1st floor sleeping

8.4 out of 10, Very good, (6)
"Perfect for a short weekend. The fact that it was a 3 mile drive to the beach was even better!"
The price is CA $123
CA $245 total
includes taxes & fees
May 5 - May 6
Tiny House Calypso with 1st floor sleeping
Casey Key Resort - Gulf Shores
Deluxe Studio, Bay View | View from room

Casey Key Resort - Gulf Shores

3.0 star property
8.2 out of 10, Very good, (254)
"Gracias por el servicio!! "
The price is CA $324
CA $385 total
includes taxes & fees
May 4 - May 5
Casey Key Resort - Gulf Shores
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, (7)
"This is decorated so cute. Very comfortable, nice location. The open living space is so comfortable. I think our rental rushed you a bit but we loved it! And appreciated it. Just remember the garbage disposal still needs a switch. The painters were very friendly and polite! "
Spacious beach cottage steps from the beach on Anna Maria Island
Studio Retreat Across the Street from Beautiful Siesta Key Beach
Property grounds

Studio Retreat Across the Street from Beautiful Siesta Key Beach

8.8 out of 10, Excellent, (149)
"We had the best getaway! Easy to walk to the town, right across the street from the beach, clean, plenty of room for two adults and two kids. We will be back!!"
The price is CA $179
CA $494 total
includes taxes & fees
Apr 28 - Apr 29
Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key Village-Suite #1: A block to the Beach!
Beach nearby, sun loungers, beach towels

Siesta Key Village-Suite #1: A block to the Beach!

9.8 out of 10, Exceptional, (37)
"We loved the property. Location is everything. Condo was clean and decorated super cute. The host was responsive to our requests alsoThe only negative is the loud air conditioning. "
Siesta Key Village-Suite #1: A block to the Beach!
Venice Beach Studio-centrally located-Great Price-Clean-Private
Beach nearby, sun loungers, beach towels

Venice Beach Studio-centrally located-Great Price-Clean-Private

10.0 out of 10, Exceptional, (9)
"We enjoyed our 4 nights here at Debbie's place.We had our privacy and never even met Debbie,we were able to say our goodbyes to her friend Barbie who was very nice. We cooked dinner one night, steak's on the grill and baked potatoes,it was perfect! Thank you Debbie for an amazing place to stay on our vacation,your studio was perfect for everything we needed. Oh and loved the high water pressure from the shower 😊"
Venice Beach Studio-centrally located-Great Price-Clean-Private
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Outdoor dining

Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

10.0 out of 10, Exceptional, (41)
"The place was very clean, well equipped outside garden is very cozy and relaxing. My son absolutely loved the hammock swings. There is also beach equipment available which was awesome. Very good communication with the host. "
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Beach nearby, sun loungers

Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

10.0 out of 10, Exceptional, (19)
"Perfect accommodations and location for family of four with two boys ages 5 7. Property was extremely clean and in a great location! Can't wait to come back."
The price is CA $276
CA $714 total
includes taxes & fees
May 14 - May 15
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
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
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4641)
"Beautiful resort. Spend a good time with my family. Definately will recommend to anyone as a great place to stay and spend a vacation."
The price is CA $219
CA $279 total
includes taxes & fees
May 4 - May 5
Tropical Beach Resorts
Anna Maria Beach Resort
On the beach, white sand, beach towels

Anna Maria Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (199)
"Highly recommend this property. Our unit was very updated and had a full kitchen with everything we needed for a comfortable stay. The beds were comfortable. The swimming pool was great and heated and the beach access was within a few steps. The location was quaint but easily accessible and lots of dining options near by. Would stay here again. "
The price is CA $538
CA $681 total
includes taxes & fees
Apr 27 - Apr 28
Anna Maria Beach Resort
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2117)
"Lovely well-appointed apartment with separate bedroom and a sitting room/kitchen. Everything you needed to cook your own food (small induction hob and a combination oven/microwave, pots etc). We only had 3 forks on arrival but quickly rectified. Despite being situated on a main road and our room being roadside, it was nice and quiet inside. Only downside was the pool being situated right next to the road - though it does get the sun for the longest there. "
The price is CA $209
CA $236 total
includes taxes & fees
May 12 - May 13
Hibiscus Suites - Gateway to Siesta Key
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.