Legacy Trail Vacation Rentals

Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Legacy Trail vacation rentals

Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (266 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
$128 nightly
The price is $145
May 4 - May 5
Total with taxes and fees
Kon Tiki Inn
Interior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (21 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
$130 nightly
The price is $144
Apr 8 - Apr 9
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (618 reviews)
"Love this place"
United States
Marialis
$189 nightly
The price is $214
May 3 - May 4
Total with taxes and fees
A Beach Retreat
Interior

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (37 reviews)
"Me and my significant other took a little mini vacation wonderful house. It was very clean very beautiful inside, I like the beach vibes beautiful bedrooms. I recommend anybody to book this place. If I had to go back, I’ll book again. "
United States
Alexus
$291 nightly
The price is $325
Apr 8 - Apr 9
Total with taxes and fees
Mimosa Memories
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,398 reviews)
"Love the location, excellent service and place clean and quite "
United States
Dayami
$226 nightly
The price is $256
Apr 12 - Apr 13
Total with taxes and fees
Tropical Beach Resorts
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (245 reviews)
"Staff very accommodating."
United States
Genevieve
$204 nightly
The price is $230
Apr 22 - Apr 23
Total with taxes and fees
Tropical Villas of Venice Beach
Beach

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (57 reviews)
"I would recommend this place to anyone! It was extremely clean and neat, and we had a lovely time here! The host was very responsive and kind too. Overall, this place was above my expectations and a great place to stay."
United States
Lana
$189 nightly
The price is $211
Apr 13 - Apr 14
Total with taxes and fees
The "Grouper"
Beach nearby, beach towels

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
$251 nightly
The price is $280
May 1 - May 2
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
Lobby

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (478 reviews)
"Exceptional location both to the beach and restaurants. The facility has everything you need to augment your stay: bikes, beach chairs and umbrellas, coolers and pool floats. The room is immaculate too."
United States
Kathy
$143 nightly
The price is $162
Apr 27 - Apr 28
Total with taxes and fees
Venice Beach Villas
Beach nearby, sun loungers, beach towels

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Lido Key
9.8 out of 10, Exceptional, (122 reviews)
"Super clean, perfect location, and cool decor - and, most important, veeerry comfortable beds! We loved our stay! "
United States
Kevin L.
$261 nightly
The price is $292
Apr 23 - Apr 24
Total with taxes and fees
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,223 reviews)
"Clean and very close to beach. "
United States
Daniel
$251 nightly
The price is $281
Apr 12 - Apr 13
Total with taxes and fees
Captiva Beach Resort
Beach nearby

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Breathtaking view- super clean. Easy access. Perfect spot for a few days away with my husband."
United States
Ellen L.
$380 nightly
The price is $418
Apr 30 - May 1
Total with taxes and fees
Best views of the beach from your balcony Unit 301
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (105 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
$278 nightly
The price is $314
May 4 - May 5
Total with taxes and fees
SeaSpray Resort
Terrace/patio

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Bradenton
9.4 out of 10, Exceptional, (72 reviews)
"Great place to stay!"
United States
Wendi B.
$166 nightly
The price is $185
Apr 12 - Apr 13
Total with taxes and fees
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
1 bedroom, desk, iron/ironing board, WiFi

Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath
Bayou Oaks
9.4 out of 10, Exceptional, (52 reviews)
"This little getaway was an anniversary celebration and it felt like we were in the perfect place to celebrate 15 years of marriage .This beautiful little house was extra clean , cozy, well decorated and well equipped, with the strawberry on top being the peacefulness and tranquillity with a short 15 min ride to the nearest beach and city center. We highly recommend the place."
United States
Juan
$113 nightly
The price is $125
Apr 20 - Apr 21
Total with taxes and fees
Riverside Oasis 1Bed/1Bath
2 bedrooms, iron/ironing board, WiFi, bed sheets

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
$438 nightly
The price is $450
Apr 12 - Apr 13
Total with taxes and fees
[escape to paradise] siesta key beach getaway
Beach nearby

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Sarasota
9.8 out of 10, Exceptional, (16 reviews)
"Wonderful location Perfect for what we wanted in a quick escape. "
United States
Antonio
Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Property grounds

Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (118 reviews)
"Perfect spot and host "
United States
Dee B.
$271 nightly
The price is $303
May 3 - May 4
Total with taxes and fees
Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs
Property grounds

Updated bayside condo with heated pool - across the street from the beach

Updated bayside condo with heated pool - across the street from the beach
Anna Maria
9.2 out of 10, Wonderful, (102 reviews)
"What a great place! Trolly pickup was two blocks away Walking distance to shops, restaurants and the beach. Can’t wait to visit again soon "
United States
Rhonda k.
$255 nightly
The price is $286
Apr 29 - Apr 30
Total with taxes and fees
Updated bayside condo with heated pool - across the street from the beach
On the beach, beach umbrellas

Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA

Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA
Longboat Key
9.2 out of 10, Wonderful, (77 reviews)
"Property was as indicated. Office staff was very friendly and accommodating. Property was quiet.We were just steps from the direct beach access."
United States
Leen S.
$309 nightly
The price is $345
Apr 14 - Apr 15
Total with taxes and fees
Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA
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

Siesta Key Palms Resort

Siesta Key Palms Resort

10/10 Excellent
"Very nice, beachy vibe. Great location. Convenient to the beach."
Donna 3-night trip
Posted 1 hour ago
Siesta Key Palms Resort

Find out more about Legacy Trail

Everything you need to know about Legacy Trail vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Legacy Trail vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Legacy Trail vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Legacy Trail. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Legacy Trail in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Legacy Trail rentals

At Expedia, we put the best Legacy Trail vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Legacy Trail rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Legacy Trail vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Legacy Trail. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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