Family home on Golf Course image 1
Family home on Golf Course image 2
Pool
Family home on Golf Course image 4
Family home on Golf Course image 5

Family home on Golf Course

4 bedrooms·4 baths
Bradenton • Florida

$2,550.00 USD total for 5 nights

Oct 1 – 6, 2026

Free cancellation
Dans Florida Condos Ocean Pearl at Runaway Bay
Dans Florida Condos Ocean Pearl at Runaway Bay
Dans Florida Condos Ocean Pearl at Runaway Bay
Dans Florida Condos Ocean Pearl at Runaway Bay
Dans Florida Condos Ocean Pearl at Runaway Bay

Dans Florida Condos Ocean Pearl at Runaway Bay

2 bedrooms·2 baths
Bradenton Beach • Florida

$2,334.52 USD total for 7 nights

Sep 7 – 14, 2026

Dans Florida Condos Dolphin Bay at Runaway Bay
Dans Florida Condos Dolphin Bay at Runaway Bay
Dans Florida Condos Dolphin Bay at Runaway Bay
Dans Florida Condos Dolphin Bay at Runaway Bay
Dans Florida Condos Dolphin Bay at Runaway Bay

Dans Florida Condos Dolphin Bay at Runaway Bay

2 bedrooms·2 baths
Bradenton Beach • Florida

$2,353.00 USD total for 7 nights

Sep 7 – 14, 2026

Dans Florida Condos Sea Esta at Runaway Bay
Dans Florida Condos Sea Esta at Runaway Bay
Dans Florida Condos Sea Esta at Runaway Bay
Dans Florida Condos Sea Esta at Runaway Bay
Dans Florida Condos Sea Esta at Runaway Bay

Dans Florida Condos Sea Esta at Runaway Bay

1 bedroom·1 bath
Bradenton Beach • Florida

$1,777.76 USD total for 7 nights

Sep 12 – 19, 2026

Dans Florida Condos Sandy Slippers at Runaway Bay
Dans Florida Condos Sandy Slippers at Runaway Bay
Dans Florida Condos Sandy Slippers at Runaway Bay
Dans Florida Condos Sandy Slippers at Runaway Bay
Dans Florida Condos Sandy Slippers at Runaway Bay

Dans Florida Condos Sandy Slippers at Runaway Bay

2 bedrooms·2 baths
Bradenton Beach • Florida

$2,467.80 USD total for 7 nights

Sep 12 – 19, 2026

Dans Florida Condos Sea Dream at Runaway Bay
Dans Florida Condos Sea Dream at Runaway Bay
Dans Florida Condos Sea Dream at Runaway Bay
Dans Florida Condos Sea Dream at Runaway Bay
Dans Florida Condos Sea Dream at Runaway Bay

Dans Florida Condos Sea Dream at Runaway Bay

2 bedrooms·2 baths
Bradenton Beach • Florida

$2,169.88 USD total for 7 nights

Sep 7 – 14, 2026

Gulf Drive Living
Gulf Drive Living
Gulf Drive Living
Gulf Drive Living
Gulf Drive Living

Gulf Drive Living

2 bedrooms·1 bath
Holmes Beach • Florida

$3,150.00 USD total for 7 nights

Sep 7 – 14, 2026

Casa Bonita image 1
Casa Bonita image 2
Casa Bonita image 3
Casa Bonita image 4
Casa Bonita image 5

Casa Bonita

3 bedrooms·3½ baths
Bradenton Beach • Florida
5(13 reviews)

$2,674.00 USD total for 5 nights

Sep 12 – 17, 2026

DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!
DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!
DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!
DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!
3-story Townhouse (Living areas on 2nd and 3rd Floors)

DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!

3 bedrooms·2½ baths
Bradenton Beach • Florida
5(149 reviews)

$2,856.61 USD total for 7 nights

Sep 12 – 19, 2026

Making Waves
Making Waves
Making Waves
Making Waves
Making Waves

Making Waves

3 bedrooms·3 baths
Bradenton Beach • Florida
5(1 review)

$3,988.00 USD total for 4 nights

Sep 13 – 17, 2026

Golf Course Condo
Golf Course Condo
Golf Course Condo
Golf Course Condo
Golf Course Condo

Golf Course Condo

2 bedrooms·2 baths
Sarasota • Florida

$3,665.00 USD total for 30 nights

Sep 7 – Oct 7, 2026

View of condo from Sarasota Bay.
View of complex from public beach/Coquina Beach
Community pool
Sunrise over Sarasota Bay from condo decks/bedroom/living room
Sunset of the Gulf from condo and public beach/Coquina Beach

Sunrise/Sunset

2 bedrooms·2 baths
Bradenton Beach • Florida

$2,815.25 USD total for 7 nights

Sep 7 – 14, 2026

The Surof House
The Surof House
The Surof House
The Surof House
The Surof House

The Surof House

2 bedrooms·1 bath
Bradenton Beach • Florida
5(2 reviews)

$1,869.45 USD total for 3 nights

Sep 7 – 10, 2026

Freshly harvested coconuts await your arrival for every person in your booking. (No additional charge). So plan to grab a coconut, set up your beach chair and put your feet in the white sands of Anna Maria Island. Cheers to a relaxing getaway!
Cozy but comfortable living room area.
Main bedroom with queen bed with calm blue accents and comfortable bedding.
2nd bedroom with a twin bed over full bunkbed. Closet space for storage.
Back patio sitting area with comfortable plush sectional sofa and arm chairs facing park and small mangrove preserve.

Coconuts included!+Family Friendly!+Close to Beach

2 bedrooms·2 baths
Holmes Beach • Florida
5(1 review)

$1,696.08 USD total for 7 nights

Sep 9 – 16, 2026

the Seaside 21 image 1
the Seaside 21 image 2
the Seaside 21 image 3
the Seaside 21 image 4
the Seaside 21 image 5

the Seaside 21

2 bedrooms·2 baths
Holmes Beach • Florida
4.77(22 reviews)
$280 – $750/ night(excl. fees & taxes)
Gulf Access
Gulf Access
Gulf Access
Gulf Access
Gulf Access

Gulf Access

4 bedrooms·4½ baths
Longboat Key • Florida

$60,500.00 USD total for 30 nights

Sep 7 – Oct 7, 2026

Just at the bottom of the stairs! The beach awaits...!
Welcome to Silver Sands, Unit 256 on Longboat Key!
We're right on the Gulf! No need to cross a busy street to get to the beach!
A bird's eye view!
Silver Sands Gulf Beach Resort -- iconic, well-known (and loved!), old Florida charm, located on Gulf of Mexico Dr., beach side, just 35 units!

Tropical Beach Condo!

1 bedroom·1 bath
Longboat Key • Florida
5(11 reviews)

$1,153.60 USD total for 3 nights

Sep 21 – 24, 2026

Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views

Golf Course and Private Pool Views

2 bedrooms·2 baths
Manatee County • Florida

$13,700.00 USD total for 60 nights

Sep 7 – Nov 6, 2026

Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

3 bedrooms·3 baths
Holmes Beach • Florida
5(7 reviews)

$1,529.61 USD total for 3 nights

Sep 7 – 10, 2026

Gulf-to-Bay Living on Longboat Key
Gulf-to-Bay Living on Longboat Key
Gulf-to-Bay Living on Longboat Key
Gulf-to-Bay Living on Longboat Key
Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

2 bedrooms·2 baths
Longboat Key • Florida

$25,878.00 USD total for 120 nights

Sep 7, 2026 – Jan 5, 2027

balcony + Gulf view
Living room with Gulf view
059-Unit 401-5
060-Unit 401-6
Beachfront Escape – Private Balcony, Gulf Views image 5

Panoramic Gulf View with Amazing Sunset.

1 bedroom·1 bath
Longboat Key • Florida
4.87(223 reviews)

$1,266.73 USD total for 3 nights

Sep 23 – 26, 2026

Renovated Beach Paradise. Ground Floor unit 64 image 1
052-Unit 64-2
059-Unit 64-9
058-Unit 64-8
060-Unit 64-10

Turtle Crawl Inn 64

1 bedroom·1 bath
Longboat Key • Florida
4.88(73 reviews)

$932.25 USD total for 3 nights

Sep 22 – 25, 2026

Right on the beach.Renovated ground Floor unit 63. image 1
020-Unit 63-4
023-Unit 63-7
024-Unit 63-8
Right on the beach.Renovated ground Floor unit 63. image 5

Turtle Crawl Inn 63

0 bedrooms·1 bath
Longboat Key • Florida
4.74(88 reviews)

$781.96 USD total for 3 nights

Sep 7 – 10, 2026

Private pool
Dinning room and kitchen
Fully stocked kitchen
Full stocked kitchen
Full stocked kitchen

Tropical Escape Sarasota

3 bedrooms·2 baths
Sarasota • Florida

$2,130.00 USD total for 7 nights

Sep 7 – 14, 2026