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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Condo Rentals in Legacy Trail and around

Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1122)
"Everything was perfect with our stay. We will be back soon."
Captiva Beach Resort
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (426)
"Everything was great. Great people to work with."
Venice Beach Villas
Anna Maria Sunsets - studio
Property grounds

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (213)
" Very clean great location and property owner very nice and understanding thank you for everything "
The price is €221
includes taxes & fees
10 Aug - 11 Aug
Anna Maria Sunsets - studio
Anna Maria Beach Condo 1/1
Beach

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (223)
"This is a great condo. Super clean, super spacious. Host was very responsive. It’s right across the street from the beach. I highly recommend and would stay again."
The price is €290
includes taxes & fees
14 Aug - 15 Aug
Anna Maria Beach Condo 1/1
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
On the beach

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

8.8 out of 10, Excellent, (21)
"Great view and nice place for a short stay. "
The price is €409
includes taxes & fees
7 Sept - 8 Sept
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Anna Maria Sunsets - studio
Sun-loungers, beach towels

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (231)
"Perfect retreat from the beach. Wonderful shower, all you need for a beach day staycation."
The price is €205
includes taxes & fees
17 Aug - 18 Aug
Anna Maria Sunsets - studio
~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ END OF SUMMER SPECIALS ~
On the beach, sun-loungers, beach towels

~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ END OF SUMMER SPECIALS ~

10.0 out of 10, Exceptional, (87)
"My husband and I celebrated our anniversary here for the week. If you enjoy staying right on the beach and walking to area shops and restaurants this is a great place! If you do not want to walk you can catch a ride on the trolley which takes you anywhere on the island. Very clean, fun location. It was small, but perfect for the two of us. Beautiful sunsets and lots of walks on the beach. Highly recommend! "
~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ END OF SUMMER SPECIALS ~
Palm Bay Club Private Balcony Beach Side
Pool

Palm Bay Club Private Balcony Beach Side

2.0 star property
8.8 out of 10, Excellent, (13)
"Nice location, clean place, great communication even when our family hit some bumps with our trip. Overall highly recommend and and plan to return. "
Palm Bay Club Private Balcony Beach Side
Beachfront condo with amazing views!
On the beach

Beachfront condo with amazing views!

10.0 out of 10, Exceptional, (37)
"Very nice view, nice location. Was super clean and had everything needed for our stay."
The price is €744
includes taxes & fees
14 Aug - 15 Aug
Beachfront condo with amazing views!
Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
9.8 out of 10, Exceptional, (9)
"Wonderful place to stay, quiet, close to the beach and wonderful restaurants within walking distance! Highly recommend!!!"
The price is €465
includes taxes & fees
11 Aug - 12 Aug
Chadwick Cove Resort & Marina
Anna Maria Island - 2/1
Property grounds

Anna Maria Island - 2/1

9.6 out of 10, Exceptional, (167)
"Property worked great for our family "
The price is €300
includes taxes & fees
10 Aug - 11 Aug
Anna Maria Island - 2/1
Spectacular Beach View! Right on Beach! Amazing views!!
On the beach, sun-loungers

Spectacular Beach View! Right on Beach! Amazing views!!

9.8 out of 10, Exceptional, (143)
"I really appreciated the owner and her interest in making sure everything was perfect during our stay! She was awesome!"
Spectacular Beach View! Right on Beach! Amazing views!!
Paradise 🏝Beach heaven 🌞condo 🦩<br>
Beach nearby, sun-loungers, beach towels

Paradise 🏝Beach heaven 🌞condo 🦩<br>

9.6 out of 10, Exceptional, (47)
"very convenient to shopping and touring the Englewood/ Venice/Punta Gorda area"
Paradise 🏝Beach heaven 🌞condo 🦩<br>
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
On the beach, sun-loungers

1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

9.6 out of 10, Exceptional, (157)
"We could not have been happier with this location and its proximity to the beach and the pools. It was also close to great restaurants by locals who proudly serve great food!! "
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
Beach nearby, beach umbrellas

2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

9.2 out of 10, Wonderful, (68)
"Nice location lots of hurricane damage"
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
Amazing beach getaway pool condo by the beach
Beach nearby

Amazing beach getaway pool condo by the beach

9.4 out of 10, Exceptional, (51)
"This spot was a perfect place for a family of four. The proximity to the beach and restaurants was excellent. Check in and check out were seamless and we had everything we needed. Great value. "
The price is €627
includes taxes & fees
10 Aug - 11 Aug
Amazing beach getaway pool condo by the beach
Amazing Condo! Restored from Hurricane!
On the beach, sun-loungers

Amazing Condo! Restored from Hurricane!

9.8 out of 10, Exceptional, (159)
"Quiet area with excellent beach access! Thank you"
Amazing Condo! Restored from Hurricane!
5 Minutes from Siesta Key!
Beach nearby, sun-loungers, beach towels

5 Minutes from Siesta Key!

9.6 out of 10, Exceptional, (33)
"Unit was clean, great location and comfortable. Communication was great. Would stay again. "
5 Minutes from Siesta Key!
Waterfront, Gulf Views,kayaks,SUP ,1 pet. Pool & tennis are closed at this time
Exterior

Waterfront, Gulf Views,kayaks,SUP ,1 pet. Pool & tennis are closed at this time

10.0 out of 10, Exceptional, (105)
"House was perfect for our family. Beach and pool are just a short walk and the dock was perfect."
Waterfront, Gulf Views,kayaks,SUP ,1 pet. Pool & tennis are closed at this time
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
On the beach

Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC

6.6 out of 10, (7)
"Great location and beach access- pool is awesome! Unit doesn’t face the ocean, but it’s right there! Very low key- place is very clean. WiFi is spotty and would not be good if you are planning to work while staying- that is an island wide issue I believe- No stove, but has everything else a kitchen needs and a grill- we would come back! "
The price is €411
includes taxes & fees
11 Aug - 12 Aug
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
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

Anna Maria Beach Resort

Anna Maria Beach Resort

10/10 Excellent
"I loved my view. "
phinlet 3-night trip
Posted 20 hours ago
Anna Maria Beach Resort