Location

Dates

Guests

Vacation rentals in Anna Maria, Florida, United States

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 28 – Nov 27, 2026

Entrance to Sunray

patio outside private to Sunray

The SunRay Tiny House

XLTwin bed with nested twin below

XLTwin bed with nested twin below

The SunRay Tiny House

1 bedroom·1 bath

St. Petersburg • Florida

4(6 reviews)

$282.47 USD total for 3 nights

Oct 7 – 10, 2026

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 28 – Oct 1, 2026

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 28 – Oct 1, 2026

Primary bedroom — king bed with coastal luxury bedding, wall-mounted smart TV, and direct sliding glass door access to the private screened pool.

Coastal dining room at Sun Oasis — a farmhouse-style table set for six with blue place settings and teal glassware, teal front door visible beyond, flowing into the living room.

Full living room — two plush sofas, striped armchair, coastal round ottoman, oversized Oasis on 40th turtle 70-inch TV art, guest book on the coffee table, and the game room archway beyond.

Screened private pool with string lights for relaxing evening swims

Pool, Game Room and Fire Pit Near Madeira Beach

3 bedrooms·2 baths

St. Petersburg • Florida

5(72 reviews)

$1,001.76 USD $919.58 USD total for 3 nights

Sep 28 – Oct 1, 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Villa Blanca | Luxury 5BR Pool Home on Siesta Key

5 bedrooms·4 baths

Sarasota • Florida

5(2 reviews)

$10,632.14 USD $10,136.19 USD total for 7 nights

Dec 19 – 26, 2026

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

3 bedrooms·2 baths

Sarasota • Florida

$500.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Palmetto House

3 bedrooms·3 baths

Sarasota • Florida

$2,369.29 USD $2,161.04 USD total for 7 nights

Sep 30 – Oct 7, 2026

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 1

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 2

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 4

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 5

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 6

1Bedroom/ 10 mins to Downtown Saint Peterburg

1 bedroom·1 bath

St. Petersburg • Florida

4.36(25 reviews)

$85 – $95/ night(excl. fees & taxes)

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

0 bedrooms·1 bath

St. Petersburg • Florida

4.32(19 reviews)

$316.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Living room from hallway

Seasonal Golf-Course Townhome in The Meadows – Fully Furnished

Fully equipped kitchen opens on courtyard

Patio with golf view

Seasonal Golf-Course Townhome in The Meadows – Fully Furnished

3 bedrooms·2 baths

Sarasota • Florida

4(1 review)

$14,362.15 USD total for 75 nights

Jan 2 – Mar 18, 2027

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 28 – Oct 1, 2026

FlipFlopsOn III Vacation Rental • 3 Blocks to the water • FL’s Gulf Coast • Sleeps 6

Your boutique Mediterranean-style 2BR bungalow (4 beds) — resort level comfort + coastal charm!

Your own private resort — located on a serene palm-lined lain in Sarasota’s coveted coastal district!

Half a mile to the Siesta Key, home of Siesta Key Beach — experience the sugar white sands of America’s #1 beach!

A Mediterranean-meets-California retreat where natural textures and curated details invite beautiful living

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bedrooms·1 bath

Sarasota • Florida

5(2 reviews)

$2,384.30 USD total for 7 nights

Oct 24 – 31, 2026

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)

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)

$746.11 USD total for 3 nights

Sep 28 – Oct 1, 2026

Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 1

Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 2

Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 3

Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 4

Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 5

Sunny Bradenton Double Queen: Breakfast, Pool &Gym

1 bedroom·1 bath

Bradenton • Florida

$586.50 USD total for 3 nights

Sep 28 – Oct 1, 2026

Sunny Bradenton King Studio: Breakfast, Pool & Gym image 1

Sunny Bradenton King Studio: Breakfast, Pool & Gym image 2

Sunny Bradenton King Studio: Breakfast, Pool & Gym image 3

Sunny Bradenton King Studio: Breakfast, Pool & Gym image 4

Sunny Bradenton King Studio: Breakfast, Pool & Gym image 5

Sunny Bradenton King Studio: Breakfast, Pool & Gym

1 bedroom·1 bath

Bradenton • Florida

$586.50 USD total for 3 nights

Sep 28 – Oct 1, 2026

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)

$675.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

3 bedrooms·2 baths

Siesta Key • Florida

5(26 reviews)

$14,950.00 USD total for 28 nights

Apr 15 – May 13, 2027

Kitchen and Dining Area

The Walters

3 bedrooms·2 baths

St. Petersburg • Florida

5(21 reviews)

$774.05 USD $737.61 USD total for 3 nights

Sep 28 – Oct 1, 2026

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

$430.53 USD total for 3 nights

Sep 28 – Oct 1, 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

$466.69 USD total for 3 nights

Sep 28 – Oct 1, 2026

Heated Saltwater Pool

The pool and surrounding area features enough lighting to enjoy the Florida evenings in style!

Catch the game on the 75" TV from the HOT TUB!

Newly remodeled kitchen with new stainless steel appliances (refrigerator, induction cook top, built in microwave/oven and dishwasher).

Living Room featuring a large sectional sofa and a 55" smart TV. Sit and enjoy the abundance of natural light.

The Funky Fish House

2 bedrooms·2 baths

Sarasota • Florida

4.99(156 reviews)

$1,657.39 USD total for 5 nights

Oct 28 – Nov 2, 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)

$701.16 USD $580.93 USD total for 4 nights

Oct 24 – 28, 2026