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

Nov 18, 2026 – Jan 17, 2027

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)

$438.78 USD total for 3 nights

Nov 22 – 25, 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

$587.00 USD total for 3 nights

Nov 18 – 21, 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

$587.00 USD total for 3 nights

Nov 18 – 21, 2026

Your own private tropical escape, made for slowing down and soaking it all in. Lounge beneath the palms, gather around the fire pit, and watch the Florida sky light up at sunset. Relax, reconnect, and let vacation mode take over.

Screened-in private pool at Sun Oasis, a vacation rental in St. Petersburg, FL — crystal-clear water, lounge chairs, and lush tropical landscaping in a fully fenced backyard.

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.

Private screened pool with lounge chairs and easy indoor-outdoor access

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

Sun Oasis Heated Pool Game Room and Wood Fire Pit Near St Pete Beaches

3 bedrooms·2 baths

St. Petersburg • Florida

5(72 reviews)

$1,112.42 USD total for 3 nights

Dec 8 – 11, 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(4 reviews)

$10,481.85 USD $9,993.42 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

Nov 18 – 21, 2026

Palmetto House

3 bedrooms·3 baths

Sarasota • Florida

$2,593.12 USD total for 7 nights

Nov 29 – Dec 6, 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)

$365.00 USD total for 3 nights

Nov 18 – 21, 2026

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

Nov 18 – 21, 2026

Property grounds

Private kitchen

Beachfront Condo at La Contessa!, 3BD/3BA, Poolside Cabana, Private Fishing Pier

3 bedrooms·3 baths

Redington Beach • Florida

5(12 reviews)

$11,215.25 USD total for 30 nights

Nov 18 – Dec 18, 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

Nov 18 – 21, 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)

$2,178.64 USD total for 7 nights

Nov 28 – Dec 5, 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

$1,568.58 USD total for 3 nights

Nov 21 – 24, 2026

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)

$1,022.96 USD total for 3 nights

Nov 23 – 26, 2026

Dive into vacation mode with a sunny pool and playful float.

Resort-style St. Pete retreat with pool, game room & outdoor dining

Gather around the waterfront fire-pit seating area.

Tiki-style backyard bar with TV, ambient lighting, and private patio seating

Make game night a highlight of your stay with the foosball table.

2 Homes - 4 MN to Madiera BCH - Hottub - HTD Pool

7 bedrooms·6 baths

St. Petersburg • Florida

$2,335.00 USD total for 3 nights

Nov 18 – 21, 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)

$300/ night(excl. fees & taxes)

Living room with pullout couch

Siesta Key beach

Dusk view of front of building

Front door and porch area

Siesta Key Village Vacation Rental – Walk to Beach

2 bedrooms·1 bath

Sarasota • Florida

$745.76 USD total for 3 nights

Nov 29 – Dec 2, 2026

Treasure Boat

3 bedrooms·2 baths

Siesta Key • Florida

$1,065.75 USD total for 3 nights

Nov 28 – Dec 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)

$785.35 USD $748.35 USD total for 3 nights

Nov 18 – 21, 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

$450.87 USD total for 3 nights

Nov 18 – 21, 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

$476.86 USD total for 3 nights

Nov 18 – 21, 2026