Title: Legacy Trail Vacation Rentals from $212: Search Short-Term Rentals | Expedia.com

[Legacy Trail Travel Guide](https://expedia.com/Legacy-Trail.dx553248621532652531)[Hotels in Legacy Trail](https://expedia.com/Legacy-Trail-Hotels.d553248621532652531.Travel-Guide-Hotels)[Flights to Legacy Trail](https://expedia.com/Cheap-Flights-To-Legacy-Trail.d553248621532652531.Travel-Guide-Flights)[Car Rentals in Legacy Trail](https://expedia.com/Car-Rentals-In-Legacy-Trail.d553248621532652531.Car-Rental-Guide)[Legacy Trail Vacation Packages](https://expedia.com/Legacy-Trail.d553248621532652531.Destination-Travel-Guides)

![Legacy Trail showing a garden](https://images.trvl-media.com/place/553248635975846806/d70ae022-0498-403c-94d8-dc8f29b7750f.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248635975846806/d70ae022-0498-403c-94d8-dc8f29b7750f.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=553248621532652531&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=553248621532652531&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=553248621532652531&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=553248621532652531&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Legacy Trail vacation rentals

![Blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119180000/119174100/119174035/8c8bc2dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/120000000/119180000/119174100/119174035/ccb99030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119180000/119174100/119174035/3eac1be4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119180000/119174100/119174035/0f6f20f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Christian Retreat Conference Center 

[](https://www.expedia.com/Bradenton-Hotels-Christian-Retreat-Conference-Center.h119174035.Hotel-Information)

Bradenton

10/10

Exceptional

(2 reviews)

"The room was clean and comfortable. The staff was courteous. The amenities were fabulous! God bless!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Javier

$111 nightly

$125 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-Christian-Retreat-Conference-Center.h119174035.Hotel-Information)

![Cabin (Tiny House - Green Lifeguard Stand) | Living area | Flat-screen TV, Netflix, streaming services](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/c4c71831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/69212d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin (Tiny House - Seashell) | Individually decorated, individually furnished, soundproofing, free WiFi](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/564d78d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin (Tiny House - The Siesta) | Private kitchen | Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/aa92991f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tiny House Siesta

[](https://www.expedia.com/Sarasota-Hotels-Tiny-House-Siesta.h21430911.Hotel-Information)

Sarasota

8.4/10

Very Good

(351 reviews)

"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Justice

$188 nightly

$212 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Tiny-House-Siesta.h21430911.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/6bac86e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/75202b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/7ac2a9bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/8b673c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #3 Small house walking distance to Warm Mineral Spring

[](https://www.expedia.com/North-Port-Hotels-3-Small-House-Walking-Distance-To-Warm-Mineral-Spring.h112257831.Hotel-Information)

Warm Mineral Springs

9.0/10

Wonderful

(12 reviews)

"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jake R.

$150 nightly

$167 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/North-Port-Hotels-3-Small-House-Walking-Distance-To-Warm-Mineral-Spring.h112257831.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/101000000/100770000/100762400/100762365/d8fcba0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100770000/100762400/100762365/3b75902b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100770000/100762400/100762365/35e9b7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100770000/100762400/100762365/7beefd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The "Grouper"

[](https://www.expedia.com/Bradenton-Hotels-The-Grouper.h100762365.Hotel-Information)

Sunny Shores

9.4/10

Exceptional

(46 reviews)

"We really enjoyed our stay here. So close to AMI "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Taylor B.

$189 nightly

$211 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-The-Grouper.h100762365.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/ca9e4b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/2027abfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/0a86937c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/5a3a0e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming cottage for 2 across warm mineral springs park

[](https://www.expedia.com/North-Port-Hotels-Charming-Cottage-For-2-Across-Warm-Mineral-Springs-Park.h112257306.Hotel-Information)

Warm Mineral Springs

9.0/10

Wonderful

(14 reviews)

"Property was perfect for the price."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William M.

$145 nightly

$161 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/North-Port-Hotels-Charming-Cottage-For-2-Across-Warm-Mineral-Springs-Park.h112257306.Hotel-Information)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/c128477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/273cc0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/edfdd191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/edb5b449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Floridian cottage in Historic Gulf Village

[](https://www.expedia.com/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information)

Olde Englewood Village

9.8/10

Exceptional

(60 reviews)

"Very good, great location 👍👍"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James M.

$281 nightly

$313 total

Feb 20 - Feb 21

Total with taxes and fees

[](https://www.expedia.com/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/105c6d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/7dab4f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/08b5bced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/aa27a0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chadwick Cove Resort & Marina

[](https://www.expedia.com/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information)

Manasota Key

10/10

Exceptional

(16 reviews)

"Great place and location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cathy

$669 nightly

$725 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/4404083b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/5721262a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/5db57a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/9eb2951c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Myakka River

[](https://www.expedia.com/Venice-Hotels-Myakka-River.h75989217.Hotel-Information)

Venice

9.8/10

Exceptional

(19 reviews)

"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ty

$407 nightly

$454 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Venice-Hotels-Myakka-River.h75989217.Hotel-Information)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/96dfb133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/887af080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/6e62c16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/654d6bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Riverside Oasis 1Bed/1Bath

[](https://www.expedia.com/Sarasota-Hotels-Riverside-Oasis-1bed1bath.h62599089.Hotel-Information)

Bayou Oaks

9.2/10

Wonderful

(44 reviews)

"Excellent place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

garry s.

$117 nightly

$130 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Riverside-Oasis-1bed1bath.h62599089.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/68000000/67390000/67389100/67389007/912b5dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/68000000/67390000/67389100/67389007/b4af874f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67390000/67389100/67389007/c540f9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67390000/67389100/67389007/32ecfd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Key-Village-Suite-1-A-Block-To-The-Beach.h67389007.Hotel-Information)

Siesta Key Village

9.8/10

Exceptional

(45 reviews)

"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alex

$341 nightly

$370 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Key-Village-Suite-1-A-Block-To-The-Beach.h67389007.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/a513603c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/b7c41de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/6732718a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/fcf007c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nestled in North Port. Updated 2 Bed / 1 Bath.

[](https://www.expedia.com/North-Port-Hotels-Nestled-In-North-Port-Updated-2-Bed-1-Bath.h111593945.Hotel-Information)

North Port

10/10

Exceptional

(17 reviews)

"Great place loved how clean and put together everything was would definitely stay here again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacob

$237 nightly

$265 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/North-Port-Hotels-Nestled-In-North-Port-Updated-2-Bed-1-Bath.h111593945.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/1524b831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/54938b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/c390520c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/c4cc982d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hideaways at Point Pleasant (Palm Side)

[](https://www.expedia.com/Bradenton-Hotels-The-Hideaways-At-Point-Pleasant-Palm-Side-Downtown-Bradenton.h23089447.Hotel-Information)

Bradenton

10/10

Exceptional

(169 reviews)

"perfect location and size for what we were looking for"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

michael w.

$242 nightly

$249 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-The-Hideaways-At-Point-Pleasant-Palm-Side-Downtown-Bradenton.h23089447.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27170000/27168000/27167912/fc0f4673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/28000000/27170000/27168000/27167912/f4fd1be0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/28000000/27170000/27168000/27167912/90b817f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27170000/27168000/27167912/79b73f31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hideaways at Point Pleasant (Pine Side)

[](https://www.expedia.com/Bradenton-Hotels-The-Hideaways-At-Point-Pleasant.h27167912.Hotel-Information)

Bradenton

9.8/10

Exceptional

(175 reviews)

"The property is nice and comfortably equipped. The location is very good."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

carlos b.

$240 nightly

$247 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-The-Hideaways-At-Point-Pleasant.h27167912.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/9d6a1945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/6dfb61f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/88c51812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/f3fd974c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachfront Studio – Cabana #5B by RVA

[](https://www.expedia.com/Sarasota-Hotels-Cabana-Beach-Club-5b-Suite1-BA-Resort-On-Longboat-Key-By-Rva.h23291227.Hotel-Information)

Longboat Key

8.2/10

Very Good

(74 reviews)

"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

K M.

$278 nightly

$310 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Cabana-Beach-Club-5b-Suite1-BA-Resort-On-Longboat-Key-By-Rva.h23291227.Hotel-Information)

![Sun loungers](https://images.trvl-media.com/lodging/32000000/31820000/31819900/31819843/80177dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31820000/31819900/31819843/a006d4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/32000000/31820000/31819900/31819843/322fc171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31820000/31819900/31819843/5977b0c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*Villa Bella\* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

[](https://www.expedia.com/Bradenton-Hotels-Villa-Bella-Executive-2BR-Condo-W2-Pools.h31819843.Hotel-Information)

Bradenton

9.8/10

Exceptional

(135 reviews)

"Only went to pool 1 day as spent most of the time at the beach its a nice area with lots to do and lots of nice walks and great beaches "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

David C.

$324 nightly

$363 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-Villa-Bella-Executive-2BR-Condo-W2-Pools.h31819843.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21680000/21678500/21678444/25cd6471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/22000000/21680000/21678500/21678444/ff579f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/22000000/21680000/21678500/21678444/af4423ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/22000000/21680000/21678500/21678444/4f166783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

[](https://www.expedia.com/Bradenton-Hotels-Kapok-In-Bradenton.h21678444.Hotel-Information)

Sunny Shores

9.4/10

Exceptional

(35 reviews)

"Excellent for a family trip."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

RHEA

$514 nightly

$549 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-Kapok-In-Bradenton.h21678444.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/68000000/67390000/67383400/67383396/73af8e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/68000000/67390000/67383400/67383396/19afa343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67390000/67383400/67383396/c5c78f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/68000000/67390000/67383400/67383396/855d1ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Siesta Cooler: Only Minutes Walk to Siesta Beach!

[](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Cooler-Only-Minutes-Walk-To-Siesta-Beach.h67383396.Hotel-Information)

Siesta Key Village

9.6/10

Exceptional

(63 reviews)

"Host was great, clean room, balcony was nice. It’s on the Main Street so not quite until the bars closed. Overall a great place to visit. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brandon N.

[](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Cooler-Only-Minutes-Walk-To-Siesta-Beach.h67383396.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/9a646a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/7542a46d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/9b700b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Pets Not Allowed | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/cc664fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kon Tiki Inn

[](https://www.expedia.com/Venice-Hotels-Kon-Tiki-Inn.h90021825.Hotel-Information)

Venice Island

10/10

Exceptional

(254 reviews)

"Great place! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle

$243 nightly

$275 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Venice-Hotels-Kon-Tiki-Inn.h90021825.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/a321ba46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/678ba916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/e1b5a198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/9b74f4a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \[escape to paradise\] siesta key beach getaway

[](https://www.expedia.com/Siesta-Key-Hotels-Modern-Beach-Bungalow-Garden-Views-Patio.h90765870.Hotel-Information)

Siesta Key

9.8/10

Exceptional

(26 reviews)

"Clean and comfortable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laney

$438 nightly

$450 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Siesta-Key-Hotels-Modern-Beach-Bungalow-Garden-Views-Patio.h90765870.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/63000000/62990000/62980700/62980630/bc837381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/63000000/62990000/62980700/62980630/41fadfc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/63000000/62990000/62980700/62980630/0215f6a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/63000000/62990000/62980700/62980630/47c8dd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Freshly Remodeled Island Suite w/ Pool & Pet Friendly

[](https://www.expedia.com/Sarasota-Hotels-Well-Furnished-Beach-Condo-Wshared-Swimming-Pool.h62980630.Hotel-Information)

Anna Maria

8.2/10

Very Good

(44 reviews)

"Nice warm pool, great they had some beach stuff to use, very quiet and nice stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Isaac L.

$312 nightly

$348 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Well-Furnished-Beach-Condo-Wshared-Swimming-Pool.h62980630.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-05&endDate=2026-03-06&regionId=553248621532652531&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

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Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Legacy+Trail%2C+Florida%2C+United+States+of+America&regionId=553248621532652531&latLong=27.230443%2C-82.473488&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=APART_HOTEL)

Apartments

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Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Legacy+Trail%2C+Florida%2C+United+States+of+America&regionId=553248621532652531&latLong=27.230443%2C-82.473488&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=VACATION_HOME)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Legacy+Trail%2C+Florida%2C+United+States+of+America&regionId=553248621532652531&latLong=27.230443%2C-82.473488&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=VILLA)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Legacy+Trail%2C+Florida%2C+United+States+of+America&regionId=553248621532652531&latLong=27.230443%2C-82.473488&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Legacy+Trail%2C+Florida%2C+United+States+of+America&regionId=553248621532652531&latLong=27.230443%2C-82.473488&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=COTTAGE)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Legacy+Trail%2C+Florida%2C+United+States+of+America&regionId=553248621532652531&latLong=27.230443%2C-82.473488&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=HOUSE_BOAT)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Legacy+Trail%2C+Florida%2C+United+States+of+America&regionId=553248621532652531&latLong=27.230443%2C-82.473488&adults=2&startDate=2026-05-20&d1=2026-05-20&endDate=2026-05-23&d2=2026-05-23&lodging=RESIDENCE)

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## Top Legacy Trail Hotel Reviews

![Compass Hotel by Margaritaville Anna Maria Sound](https://images.trvl-media.com/lodging/42000000/41970000/41961400/41961327/8b0dc5d5_y.jpg)

### Compass Hotel by Margaritaville Anna Maria Sound

10/10 Excellent

"Everything seemed right. The location close to beaches, preserves and not far from Sarasota."

[](https://expedia.com/Sarasota-Hotels-Compass-Hotel-By-Margaritaville.h41961327.Hotel-Information)

![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg)

### Carlisle Inn

10/10 Excellent

"Great room and very helpful,friendly staff at checkin. "

[](https://expedia.com/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information)

![Hyatt Place Sarasota/Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg)

### Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent

"Staff was great, room was clean will stay again "

[](https://expedia.com/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information)

![Siesta Key Palms Resort](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/86bd1cda_y.jpg)

### Siesta Key Palms Resort

10/10 Excellent

"This was a excellent get away for valentines weekend"

[](https://expedia.com/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information)

![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg)

### Golden Host Resort - Sarasota

10/10 Excellent

"It was all great. We enjoyed"

[](https://expedia.com/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information)

![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg)

### Kompose Boutique Hotel

10/10 Excellent

"Very modern room, exceptionally clean. Really nice breakfast. Staff is very friendly. "

[](https://expedia.com/Sarasota-Hotels-Kompose-Boutique-Hotel.h38215316.Hotel-Information)

![Zota Beach Resort](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/277458de_y.jpg)

### Zota Beach Resort

10/10 Excellent

"Great atmosphere and good! Rooms were very nice and clean. Staff was super friendly. I loved the valet parking. Free beach chairs included in the resort fee was a great benefit. The pool was nice and heated for a February stay. I highly recommend. "

[](https://expedia.com/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information)

![Spark by Hilton Sarasota Siesta Key Gateway](https://images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg)

### Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"Very nice place"

[](https://expedia.com/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information)

![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg)

### Tropical Beach Resorts

10/10 Excellent

"Room was clean and was walking distance to plenty of amenities. Had a great time."

[](https://expedia.com/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information)

## 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 $212 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.

## Explore a world of travel with Expedia

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- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
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- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Legacy Trail ](https://expedia.com/Legacy-Trail-Private-Vacation-Homes.d553248621532652531-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Legacy Trail ](https://expedia.com/Legacy-Trail-Condos.d553248621532652531-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Legacy Trail ](https://expedia.com/Legacy-Trail-Apartments.d553248621532652531-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Legacy Trail ](https://expedia.com/Legacy-Trail-Cottages.d553248621532652531-aaCottages.Travel-Guide-Accommodation)
- [Villas in Legacy Trail ](https://expedia.com/Legacy-Trail-Villas.d553248621532652531-aaVillas.Travel-Guide-Accommodation)
- [Motels in Legacy Trail ](https://expedia.com/Legacy-Trail-Motels.d553248621532652531-aaMotels.Travel-Guide-Accommodation)
- [Aparthotels in Legacy Trail ](https://expedia.com/Legacy-Trail-Apart-Hotels.d553248621532652531-aaApartHotels.Travel-Guide-Accommodation)
- [Resorts in Legacy Trail ](https://expedia.com/Legacy-Trail-Resorts.d553248621532652531-aaResorts.Travel-Guide-Accommodation)
- [Houseboats in Legacy Trail ](https://expedia.com/Legacy-Trail-Houseboats.d553248621532652531-aaHouseboats.Travel-Guide-Accommodation)
- [B&B in Legacy Trail ](https://expedia.com/Legacy-Trail-Bed-And-Breakfast.d553248621532652531-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [RV Parks in Legacy Trail ](https://expedia.com/Legacy-Trail-RV-Parks.d553248621532652531-aaRVParks.Travel-Guide-Accommodation)
- [Guest Houses in Legacy Trail ](https://expedia.com/Legacy-Trail-Guest-Houses.d553248621532652531-aaGuestHouses.Travel-Guide-Accommodation)

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- [Hotel Rooms in Clearwater](https://expedia.com/Clearwater-Hotels.d6033.Travel-Guide-Hotels)
- [Hotel Rooms in Clearwater Beach](https://expedia.com/Clearwater-Beach-Hotels.d10759.Travel-Guide-Hotels)
- [Hotel Rooms in Miami Beach](https://expedia.com/Miami-Beach-Hotels.d8833.Travel-Guide-Hotels)
- [Disney SpringsTM hotels](https://expedia.com/Disney-SpringsTM-Hotels.0-l502131-0.Travel-Guide-Filter-Hotels)
- [Clearwater Beach Oceanfront Hotels](https://expedia.com/Clearwater-Beach-Hotels-Oceanfront-Hotels.0-0-d10759-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Jacksonville Beach](https://expedia.com/Jacksonville-Beach-Hotels.d8196.Travel-Guide-Hotels)
- [Walt Disney World® Resort hotels](https://expedia.com/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels)
- [Port Everglades hotels](https://expedia.com/Port-Everglades-Hotels.0-l6124927-0.Travel-Guide-Filter-Hotels)

Flights

- [Flights to TPA](https://expedia.com/Cheap-Flights-To-Clearwater-Beach.d10759.Travel-Guide-Flights)

Cars

- [Car rental Miami Airport (MIA)](https://expedia.com/Car-Rentals-In-Miami-Intl.d4278605.Car-Rental-Guide)
- [Car rental Jacksonville Airport (JAX)](https://expedia.com/Car-Rentals-In-Jacksonville-Intl.d5783882.Car-Rental-Guide)
- [Car rental Fort Myers Airport (RSW)](https://expedia.com/Car-Rentals-In-Southwest-Florida-Intl.d5722962.Car-Rental-Guide)
- [Car rental Fort Lauderdale Airport (FLL)](https://expedia.com/Car-Rentals-In-Fort-Lauderdale-Hollywood-Intl.d5000262.Car-Rental-Guide)
- [Car rental Tampa Airport (TPA)](https://expedia.com/Car-Rentals-In-Tampa-Intl.d4280404.Car-Rental-Guide)
- [Car rental Sarasota Airport (SRQ)](https://expedia.com/Car-Rentals-In-Sarasota-Bradenton-Intl.d6032075.Car-Rental-Guide)
- [Car rental Orlando Airport (MCO)](https://expedia.com/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide)
- [Car rental Sanford Airport (SFB)](https://expedia.com/Car-Rentals-In-Orlando-Sanford-Intl.d6031813.Car-Rental-Guide)
- [Car rental West Palm Beach Airport (PBI)](https://expedia.com/Car-Rentals-In-Palm-Beach-Intl.d4801104.Car-Rental-Guide)

Cruises

- [Cruises from Port Canaveral](https://expedia.com/Cruises-from-Port-Canaveral.d6127851.Cruise-Departure-Port)

Packages

- [Walt Disney World® Resort](https://expedia.com/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction)
- [Holiday in Clearwater Beach](https://expedia.com/Clearwater-Beach.d10759.Destination-Travel-Guides)

General

- [Visit Downtown Miami](https://expedia.com/Miami-Downtown-Miami.dx800070)

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