Houses Longboat Key

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1,905 houses

BEACHFRONT 2BD / 2BA CONDO -- OVER 1,225 sq.ft. in heart of Paradise!

Redington Shores house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 17 minutes

Match: Rental types Staffed property Golf course on site or within 15 min walk

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Price per night from

$344

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Northeast St Petersburg 1950's Cottage 3701

St. Petersburg house

2 bedrooms / 1 bathroom / sleeps 8

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$131

Pass-A-Grille Key West Style Main House 108-18

St. Pete Beach house

2 bedrooms / 2 bathrooms / sleeps 4

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$362

Bradenton Retreat

Bradenton house

2 bedrooms / 1 bathroom / sleeps 4

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$144

Tranquility at the Preserve

Sarasota house

4 bedrooms / 5 bathrooms / sleeps 10

“very nice and clean” everything worked out great!!! we would stay and recommend this house to anyone coming into town or just get a way.

Responds fast! avg. 1 hour 19 minutes

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$275

Rock Lobster Cottage 2

Treasure Island house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 58 minutes

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$92

Rock Lobster 1

Treasure Island house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 58 minutes

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$86

Pass-A-Grille Key West Style Compound 108-18

Tierra Verde house

4 bedrooms / 4 bathrooms / sleeps 8

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$539

Jacaranda (ANN775)

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 28 minutes

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$385

Bay Boulevard (ANN765)

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 28 minutes

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$385

St Pete Haven

Bay Pines house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 58 minutes

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$144

Sarasota Pinecraft Cottage 2

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 16 minutes

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$149

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$144

A Paradise for Golfers and Tennis players

Bradenton apartment

3 bedrooms / 2 bathrooms / sleeps 6

“River strand condo” Been here 1 week and everything has been great. Owners are very helpful. River Strand has great golf, tennis, pools.

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$139

Siesta Key Public Beach

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 6

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$161

Pass-A-Grille Key West Style Guest House 108-18

St. Pete Beach house

2 bedrooms / 2 bathrooms / sleeps 4

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$243

St. Pete Beach Belle Vista Bungalow 154

Tierra Verde house

2 bedrooms / 2 bathrooms / sleeps 4

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$126

Pass-A-Grille Way Gulfway Tucked Away102-22

Tierra Verde house

6 bedrooms / 3 bathrooms / sleeps 13

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$911

Beautiful and luxurious home located in Venice, Florida

Venice house

4 bedrooms / 2 bathrooms / sleeps 8

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$95

Jungle Terrace 3 Acre Mediterranean Home Pool 3401

Kenneth City house

3 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$252

NEW LISTING! Welcoming retreat w/shared pool, nearby golf, shops & restaurants

Bradenton house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 20 minutes

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$122

Lakefront condo w/ shared pool, tennis, on-site golf & scenic views

Fruitville house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 19 minutes

2 of 3 match: Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$90

BEACH ESCAPE, FAMILY FRIENDLY 2BR/2BA APARTMENT, POOL, TIKI BAR, FREE PARKING

Treasure Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$227

NEW LISTING! GULF VIEW 2BR/2BA GEM FOR 6 GUESTS, 2 POOLS, HOT TUB, PARKING

Treasure Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$227

INCREDIBLE 2BR/2BA WITH GULF VIEW, POOL, HOT TUB, BAR, RIGHT ON THE BEACH

Treasure Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$227

Incredible 2BR/2BA with Gulf View, Direct Beach Access, Pool, Parking, Balcony

Treasure Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$227

BEACH ESCAPE, 3 x 2BR/2BA FOR 18 GUESTS, TIKI BAR, 2 POOLS, PARKING, BALCONY

Treasure Island apartment

6 bedrooms / 6 bathrooms / sleeps 18

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$666

BEACH VACAY, FOUR x 2BR/2BAs APTs FOR 24 GUESTS, 2 POOLS, PARKING, HOT TUB

Treasure Island apartment

8 bedrooms / 8 bathrooms / sleeps 24

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$835

FAMILY BEACH VACATION! FANTASTIC 2BR/2BA, POOL, PARKING, HOT TUB, BALCONY

Treasure Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$227

BEACH GETAWAY, TWO 2BR/2BA APARTMENTS, POOL, PARKING, HOT TUB, BALCONY

Treasure Island apartment

4 bedrooms / 4 bathrooms / sleeps 12

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$455

4 Amazing 2BRs For 24 Guests! Gulf and Beach View, 2 Pools, Hot Tub, Parking!

Treasure Island apartment

8 bedrooms / 8 bathrooms / sleeps 24

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$887

BEACH STAY! FANTASTIC 2BR APARTMENT, POOL, PARKING, GYM, HOT TUB

Treasure Island apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$227

NEW LISTING! Three x 2BR/2BA Apartments For 18. Right On The Beach, Two Pools

Treasure Island apartment

6 bedrooms / 6 bathrooms / sleeps 18

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$666

GULF ESCAPE, FOUR x 2BR APTS FOR 24 GUESTS, POOL, PARKING, FAMILY FRIENDLY

Treasure Island apartment

8 bedrooms / 8 bathrooms / sleeps 24

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$887

BEACH PARADISE, THREE X 2BR/2BA APTs 2 POOLS, PARKING, HOT TUB, BALCONY

Treasure Island apartment

6 bedrooms / 6 bathrooms / sleeps 18

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$629

RIGHT ON THE BEACH, 2 x 2BR/2BA APTSs, FAMILY FRIENDLY, 2 POOLS, PARKING

Treasure Island apartment

4 bedrooms / 4 bathrooms / sleeps 12

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$455

NEW LISTING, Two Comfy 2BR/2BA Apartments with Balcony, Right On The Beach, Pool

Treasure Island apartment

4 bedrooms / 4 bathrooms / sleeps 12

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$411

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Rental types, Golf course on site or within 15 min walk, Staffed property

2 of 3 filters match

Price per night from

$117

Viewing 38 of 1,905
rentals in Longboat Key

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