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

Oct 20 – 27, 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)

$2,041.29 USD total for 7 nights

Oct 22 – 29, 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)

$2,233.00 USD total for 7 nights

Nov 13 – 20, 2026

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

Oct 20 – 27, 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

Oct 23 – 30, 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

Oct 23 – 30, 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

Oct 20 – 27, 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

Oct 25 – Nov 1, 2026

Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA

Beachfront Condo on Anna Maria Island, FL, USA

2 bedrooms·2 baths
Anna Maria • Florida

$3,870.00 USD total for 14 nights

Oct 20 – Nov 3, 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)

$2,508.57 USD total for 7 nights

Oct 24 – 31, 2026

Screened lanai with table and chairs
Our ground floor corner unit
Loungers in front of building
View down the beach
Aerial view of building from Gulf

Beachfront Condo in Bradenton Beach – Ground Floor

1 bedroom·1 bath
Bradenton Beach • Florida

$1,768.82 USD total for 3 nights

Dec 20 – 23, 2026

Beautiful sunset view from living room
New chairs that sit higher than railing to see over
Pathway to beach
Aerial view of building from Gulf
Loungers

Beachfront Condo in Bradenton Beach – Gulf Views

1 bedroom·1 bath
Bradenton Beach • Florida

$1,436.06 USD total for 3 nights

Nov 5 – 8, 2026

Making Waves
Making Waves
Making Waves
Making Waves
Making Waves

Making Waves

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

$4,194.00 USD total for 4 nights

Nov 14 – 18, 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(9 reviews)

$14,959.60 USD total for 28 nights

Oct 20 – Nov 17, 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)

$2,799.00 USD total for 5 nights

Oct 24 – 29, 2026

Tranquility on the bay. image 1
Tranquility on the bay. image 2
Tranquility on the bay. image 3
Tranquility on the bay. image 4
Tranquility on the bay. image 5

Tranquility on the bay.

2 bedrooms·2 baths
Bradenton • Florida
4.99(159 reviews)

$610.51 USD total for 3 nights

Oct 26 – 29, 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)

$3,083.82 USD total for 3 nights

Oct 25 – 28, 2026

My Sunny home on the Bay. image 1
My Sunny home on the Bay. image 2
My Sunny home on the Bay. image 4
My Sunny home on the Bay. image 5
My Sunny home on the Bay. image 6

My Sunny home on the Bay.

2 bedrooms·2 baths
Bradenton • Florida
4.98(273 reviews)

$576.61 USD total for 3 nights

Oct 26 – 29, 2026

My Peaceful place on the bay. image 1
My Peaceful place on the bay. image 2
My Peaceful place on the bay. image 3
My Peaceful place on the bay. image 4
My Peaceful place on the bay. image 5

My Peaceful place on the bay.

2 bedrooms·2 baths
Bradenton • Florida
4.99(187 reviews)

$549.49 USD total for 3 nights

Oct 28 – 31, 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

Oct 20 – 27, 2026

Stunning Gulf Views, Elevator to All Floors, Mini Golf, Heated Pool/Spa
Fun in the sun starts here - Hosted by RentAnnaMaria
Sunset Views from Shore to Please! - Hosted by RentAnnaMaria
Shore to Please - Hosted by RentAnnaMaria
Amazing Views! Main Living Space (3rd Floor) - Elevator to All Floors - Hosted by RentAnna Maria

Shore to Please

5 bedrooms·4½ baths
Anna Maria • Florida
5(13 reviews)

$3,035.32 USD total for 4 nights

Nov 8 – 12, 2026

Coastal Palm Hideaway
Coastal Palm Hideaway
Coastal Palm Hideaway
Coastal Palm Hideaway
Coastal Palm Hideaway

Coastal Palm Hideaway

4 bedrooms·2 baths
Bradenton • Florida
4.92(62 reviews)

$868.97 USD total for 3 nights

Oct 20 – 23, 2026

Gulf Access
Gulf Access
Gulf Access
Gulf Access
Gulf Access

Gulf Access

4 bedrooms·4½ baths
Longboat Key • Florida

$2,000.00 USD total for 3 nights

Oct 20 – 23, 2026

Guests love the outdoor space of this home, which includes a heated pool, covered seating area with a Roku TV, outdoor dining space and mural. Everything is screened so bugs and tropical wildl
The home has a large heated pool, with new paver deck and new pool cage!
The garage of the home has foosball, darts, and a pingpong table. There are beach chairs, toys, and umbrellas available for guests to use.
Enjoy a movie night after a day at the beach! The living room has a large cozy sectional, tv, and fireplace.
The primary bedroom flows right out to the pool!

Palma Rosa

3 bedrooms·2 baths
Bradenton • Florida
5(41 reviews)

$1,101.60 USD total for 3 nights

Nov 13 – 16, 2026