Location

Dates

Guests

Vacation rentals in Gulfport, Florida, United States

Pass a Grille Historic Cottage- Beach is across the street.

Beach. Steps from the cottage

Cozy Kitchen. Small but lots of space to cook

Pass a Grille Historic Cottage- Beach is across the street.

Pass a Grille Historic Cottage- Beach is across the street.

Pass a Grille Historic Cottage- Beach is across the street.

1 bedroom·1 bath

St. Pete Beach • Florida

4.85(27 reviews)

$175 – $261/ night(excl. fees & taxes)

Magnolia near the beach and downtown St. Pete image 1

Magnolia near the beach and downtown St. Pete image 2

Magnolia near the beach and downtown St. Pete image 3

Magnolia near the beach and downtown St. Pete image 4

Magnolia near the beach and downtown St. Pete image 5

Magnolia near the beach and downtown St. Pete

5 bedrooms·3 baths

St. Petersburg • Florida

4.85(150 reviews)

$135 – $1,091/ night(excl. fees & taxes)

Casa Noir by Perez Benitez image 1

Casa Noir by Perez Benitez image 2

Casa Noir by Perez Benitez image 3

Casa Noir by Perez Benitez image 4

Casa Noir by Perez Benitez image 5

Casa Noir by Perez Benitez

4 bedrooms·2 baths

St. Petersburg • Florida

5(6 reviews)

$240 – $250/ night(excl. fees & taxes)

Common Area: 🌳 Spacious Outdoor w/ table and chairs

Welcome to your perfect retreat—ideal for a solo traveler or couple.

St. Petersburg, Florida – a vibrant city bursting with sunshine, culture, and endless possibilities! Nestled on the Gulf Coast, St. Pete is a haven for art lovers, outdoor enthusiasts, and those seeking a laid-back coastal escape

A beautifully remodeled bathroom guests love.

Step outside to your private outdoor deck, complete with a dining table and chairs—perfect for morning coffee or alfresco meals in the fresh air.

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath

St. Petersburg • Florida

$426.01 USD total for 3 nights

Sep 7 – 10, 2026

Common Area: 🌳 Spacious Outdoor w/ table and chairs

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath

St. Petersburg • Florida

$448.61 USD total for 3 nights

Sep 7 – 10, 2026

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

7 bedrooms·7 baths

Madeira Beach • Florida

$4,220.55 USD total for 3 nights

Sep 12 – 15, 2026

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

1 bedroom·1 bath

Madeira Beach • Florida

$1,194.02 USD total for 3 nights

Sep 12 – 15, 2026

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

2 bedrooms·2 baths

Madeira Beach • Florida

$1,541.33 USD total for 3 nights

Sep 12 – 15, 2026

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,315.47 USD total for 3 nights

Sep 12 – 15, 2026

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,237.15 USD total for 3 nights

Sep 12 – 15, 2026

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,237.15 USD total for 3 nights

Sep 12 – 15, 2026

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

2 bedrooms·1 bath

St. Petersburg • Florida

5(26 reviews)

$106 – $569/ night(excl. fees & taxes)

The Bayou Breeze Cottage

The Bayou Breeze Cottage

The Bayou Breeze Cottage

The Bayou Breeze Cottage

The Bayou Breeze Cottage

The Bayou Breeze Cottage

1 bedroom·1 bath

St. Petersburg • Florida

5(28 reviews)

$596.41 USD $493.13 USD total for 4 nights

Oct 6 – 10, 2026

Free cancellation

The Parkside Retreat at 78th Street

3 bedrooms·2 baths

Pinellas Park • Florida

$611.95 USD total for 3 nights

Sep 8 – 11, 2026

Pond-side ART-home with private pool. DOGS WELCOME

5 bedrooms·3 baths

Pinellas Park • Florida

5(20 reviews)

$318/ night(excl. fees & taxes)

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

1 bedroom·1 bath

Madeira Beach • Florida

$567.00 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

1 bedroom·1 bath

Madeira Beach • Florida

$567.00 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

Kitchen and Dining Area

The Walters

3 bedrooms·2 baths

St. Petersburg • Florida

5(21 reviews)

$774.05 USD total for 3 nights

Sep 8 – 11, 2026

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

2 bedrooms·2 baths

Walton County • Florida

5(12 reviews)

$739.50 USD total for 3 nights

Sep 7 – 10, 2026

Welcome to Emperor Rentals!

Have a fun and great time during your stay while swimming in this stunning heated pool with family and friends! If you are interested in this property, send us a message!

Our beautiful living area has a smart TV and a comfortable and modern L-shaped couch! Never miss an episode of your favorite series while on vacation while relaxing.

Prepare and make great meals in our wonderful spacious and fully equipped kitchen. If you love cooking, this property is great for you! Book it now!

Our spacious and secured driveway so you don't have to worry about where to park your cars! If you think this property suits your needs, send us a message!

Paradise Cove House

4 bedrooms·1 bath

Pinellas Park • Florida

5(59 reviews)

$1,104.30 USD total for 3 nights

Oct 16 – 19, 2026

Free cancellation

Beach Living & Shuffleboard

16100 2nd St - Web Quality (4)

Full-Equipped Kitchen for making family meals

16100 2nd St - Web Quality (22)

She's A Shore Thing

3 bedrooms·2 baths

Redington Beach • Florida

$194 – $593/ night(excl. fees & taxes)

Pool home in Seminole Florida

Pool home in Seminole Florida

Pool home in Seminole Florida

Pool home in Seminole Florida

Pool home in Seminole Florida

Pool home in Seminole Florida

3 bedrooms·2 baths

Seminole • Florida

$855.19 USD total for 3 nights

Sep 7 – 10, 2026

Open concept floor plan makes sure no one misses out on the fun.

The living room is cozy and functional. A 65 inch smart TV will keep anyone entertained and a desk to make sure your "out of office" is turned on.

The owner's bath is spacious and luxurious!

You will enjoy the owner's suite with a king size bed and private access to the pool.

Twin Palms Oasis

3 bedrooms·2 baths

Pinellas County • Florida

4.79(33 reviews)

$670.06 USD $627.73 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

Welcome to the Lakeside Retreat -This tranquil estate awaits!

Nestled right on Lake Seminole, the backyard gazebo and pool area provide stunning views!

Our unique 4-plex floor plan gives your large group the ability to gather…

…while still having moments of privacy in their own suites.

Each suite is inspired by one of the 4 elements: Earth, Air, Fire, & Water

Lakeside Retreat-4plex Sleeps 20

9 bedrooms·5 baths

Largo • Florida

5(19 reviews)

$5,520.00 USD total for 3 nights

Sep 7 – 10, 2026