Secluded backyard
Private saltwater pool
So close to the beach!
Bliss by the Beach- Beach Boutique Rentals
Beautiful and open kitchen

Bliss by the Beach

2 bedrooms·2 baths
Anna Maria • Florida

$3,787.95 USD total for 5 nights

Jun 5 – 10, 2027

A pool unlike any other
Fun beyond the beach awaits
Welcome to Beachfront Bliss
Welcome to unforgettable island living
Open living area made for gathering

Beachfront Bliss

5 bedrooms·5½ baths
Anna Maria • Florida

$11,411.84 USD total for 7 nights

Nov 13 – 20, 2026

Experience luxury!
Beautiful backyard at any time of the day
Amazing views from the top deck
Almost bay front location

Pier to Pier Paradise

4 bedrooms·4½ baths
Anna Maria • Florida

$4,973.26 USD total for 7 nights

Nov 16 – 23, 2026

Sunny Limelight pool
See how close you are to the beach
Welcome to Limelight!
Bright open living space

Limelight

3 bedrooms·2 baths
Anna Maria • Florida

$3,055.60 USD total for 7 nights

Nov 12 – 19, 2026

Poolside backyard retreat
Kick back and relax poolside
Welcome to Bay Bungalow
Step inside the open living space
Recently updated interior with new furniture

Bay Bungalow

3 bedrooms·2 baths
Anna Maria • Florida

$3,046.98 USD total for 7 nights

Nov 29 – Dec 6, 2026

Huge pool with attached spa
Welcome to Paradise Blu!
Huge tropical yard and pool
Grand living room with views

Paradise Blu

4 bedrooms·4½ baths
Anna Maria • Florida
5(2 reviews)

$5,719.15 USD total for 7 nights

Nov 15 – 22, 2026

Welcome to Luxe Island Escape
Multi-level decks overlooking the pool
Main foyer
Amazing views from every room

Luxe Island Escape

4 bedrooms·4½ baths
Anna Maria • Florida
5(1 review)

$6,088.41 USD total for 7 nights

Nov 10 – 17, 2026

Blissful pool and spa
Huge backyard paradise
Welcome to adorable Anna Margaritas
Come on in!
Welcoming open floor plan

Anna Margaritas

2 bedrooms·2 baths
Anna Maria • Florida

$3,096.21 USD total for 7 nights

Dec 8 – 15, 2026

Resort-style backyard retreat
Welcome to the Veranda on Jacaranda
Tropical vacation begins here

The Veranda on Jacaranda

4 bedrooms·3½ baths
Anna Maria • Florida

$4,295.06 USD total for 7 nights

Dec 4 – 11, 2026

Where the view becomes your backdrop
Your waterfront pool retreat awaits
Welcome to The Lookout
Your beach escape begins inside

The Lookout

3 bedrooms·2 baths
Anna Maria • Florida
5(2 reviews)

$5,229.28 USD total for 7 nights

Nov 30 – Dec 7, 2026

2 Homes, 1 Private Pool | Near IMG & AMI
2 Homes, 1 Private Pool | Near IMG & AMI
Jenga and the Washer game help let non-pool lovers still be part of the action.
The twilight is beautiful with no bugs and lots of time to have a night swim.
2 Homes, 1 Private Pool | Near IMG & AMI

2 Homes, 1 Private Pool | Near IMG & AMI

4 bedrooms·3 baths
Bradenton • Florida

$1,053.25 USD total for 3 nights

Nov 9 – 12, 2026

Brand new king bed
Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 2
Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 3
Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 4
Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 5

Luxury 2BR/2BA Condo Minutes from Beaches & IMG

2 bedrooms·2 baths
Bradenton • Florida
5(37 reviews)

$515.24 USD total for 3 nights

Nov 9 – 12, 2026

Welcome to Paradise
Welcome to Paradise
Welcome to Paradise
Welcome to Paradise
Welcome to Paradise

Welcome to Paradise

3 bedrooms·2 baths
Bradenton • Florida

$718.65 USD total for 3 nights

Nov 9 – 12, 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

Nov 9, 2026 – Mar 9, 2027

Screened heated salt pool, hot tub and patio. Includes new smart TV, patio furniture, picnic table and chaise lounge chairs.
Relax in our bubbling, heated salt hot tub!
Beaches + Htd Pool/Spa + Fenced Yard + Game Room! image 3
Master bedroom with new king bed, smart TV, private attached bathroom, ceiling fan and double closets.
Bedroom offers 2 new twin beds and 1 new full bed. Also includes new smart TV and ceiling fan.

AMI Beaches + Heated Salt Pool + Spa + Large Yard

3 bedrooms·2 baths
Bradenton • Florida
5(49 reviews)

$1,650.00 USD total for 3 nights

Nov 15 – 18, 2026

Boutique Style:Hot Tub*Heated Pool*Game Rm*2 Kings
Magical screened in pool surrounded by twinkling lights and multiple seating options
Bright chef’s galley kitchen with stainless appliances & ample workspace.
King bed with supportive comfortable mattress, high end cotton sheets, dedicated workspace, dresser and TV, yoga mats, 2 robes and standing mirror
Stylish lounge with sectional, big TV & chic wallpaper accent

Boutique Style:Hot Tub*Heated Pool*Game Rm*2 Kings

3 bedrooms·2 baths
Bradenton • Florida
5(44 reviews)

$937.95 USD total for 3 nights

Nov 16 – 19, 2026

Sitting Area w/fireplace and desk
Floorplan layout
Workspace w/2GB Fiber Internet
Full kitchen w/new appliances
Coffee Bar w/K-cups, tea, sugar

Bradenton Boho Bungalow

3 bedrooms·2 baths
Bradenton • Florida

$1,008.00 USD total for 3 nights

Nov 9 – 12, 2026

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)

$1,227.18 USD total for 3 nights

Nov 29 – Dec 2, 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

Nov 9 – 12, 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)

$815.86 USD total for 3 nights

Nov 9 – 12, 2026

IMG Academy, Heated Pool, Huge Game Room & Golf! image 1
IMG Academy, Heated Pool, Huge Game Room & Golf! image 2
IMG Academy, Heated Pool, Huge Game Room & Golf! image 3
IMG Academy, Heated Pool, Huge Game Room & Golf! image 4
IMG Academy, Heated Pool, Huge Game Room & Golf! image 5

Sunny Bradenton Oasis, Pool/ Near Beaches & Golf!

4 bedrooms·2 baths
Bradenton • Florida

$945.81 USD $909.82 USD total for 3 nights

Nov 9 – 12, 2026

Pompano Palms
Pompano Palms
Pompano Palms
Pompano Palms
Pompano Palms

Pompano Palms

3 bedrooms·3½ baths
Palmetto • Florida
$71/ night(excl. fees & taxes)
Float the day away!
View from our lanai - straight on out!
The sweet life!
Nice and airy!
Relax!

Condo with a View on Longboat Key

0 bedrooms·1 bath
Longboat Key • Florida
4.98(122 reviews)

$971.80 USD total for 3 nights

Nov 20 – 23, 2026

Ground Floor, Direct Oceanview on LBK!
Ground Floor, Direct Oceanview on LBK!
Ground Floor, Direct Oceanview on LBK!
Ground Floor, Direct Oceanview on LBK!
Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

0 bedrooms·1 bath
Longboat Key • Florida
5(28 reviews)

$971.80 USD total for 3 nights

Nov 9 – 12, 2026