The Cottages on the Key

03/26/2025

Soft sandy beaches and crystal clear waters of ANNA MARIA ISLAND are just a short stroll away from KAYS LANDING, located in the ❤ of Pine Avenue on AMI. Relax and enjoy!

Check availability here www.thecottagesonthekey.com/vacation-rentals/rental/kays-landing-423/

Welcome to Kay's Landing: A Breathtaking Retreat on Anna Maria IslandStep into paradise at Kay's Landing, a stunning 6-bedroom,...

03/26/2025

We loved assisting the Bradenton Area Convention & Visitors Bureau with a recent marketing photo shoot to capture Anna Maria Island’s low-rise coastline. They also captured our glorious vacation rental. The new campaign is set to launch in April.

Bradenton Gulf Islands

03/25/2025

Feel the ANNA MARIA ISLAND magic surround you! BEACH A LA MODE is your next AMI getaway. This five-bedroom canal-front home is just steps from the bustle of Pine Ave and a seven minute walk to the pristine shores of the Gulf of Mexico!

⭐Private heated pool & spa
⭐Multiple balconies - all with views and loungers
⭐Game room & private elevator

See for yourself why everyone loves BEACH A LA MODE....
www.thecottagesonthekey.com/vacation-rentals/rental/beach-a-la-mode-211/

03/24/2025

The stage is set at SHORE IS SOMETHING for your next perfect vacation on LIDO KEY! Luxury and coastal charm blend effortlessly in this HUGE stylish home with TEN bedrooms! Amazing home for large groups!
A short bike ride to St Armands shops, dining and cocktails, plus a short walk to the beautiful Lido Key beach - what's not to love?

⭐ Chefs Dream Kitchen
⭐ Private Elevator
⭐ Multiple Spacious Balconies
⭐ Heated Pool & Spa

Gather your family and friends and check availability @ https://www.thecottagesonthekey.com/vacation-rentals/rental/shore-is-something-129/

03/24/2025

The stage is set at SHORE IS SOMETHING for your next perfect vacation on LIDO KEY! Luxury and coastal charm blend effortlessly in this HUGE stylish home with TEN bedrooms!
A short bike ride to St Armands shops, dining and cocktails, plus a short walk to the beautiful Lido Key beach - what's not to love?

⭐ Chefs Dream Kitchen
⭐ Private Elevator
⭐ Multiple Spacious Balconies
⭐ Heated Pool & Spa

Gather your family and friends and check availability @ https://www.thecottagesonthekey.com/vacation-rentals/rental/shore-is-something-129/

03/23/2025

BOOK THE TRIP ✅
TAKE THE TRIP ✅
MAKE LASTING MEMORIES ✅

LUXURY VACATION RENTAL HOMES www.thecottagesonthekey.com

03/22/2025

Want to explore SIESTA KEY waterways by kayak? This is your ultimate, colorful, canal front home with a fishing dock and kayaks provided for outdoor adventures! LATITUDE ADJUSTMENT has 4 bedrooms and balconies for watching the local wildlife, plus only a few minutes from the fine white sand and crystal clear waters of SIESTA KEY BEACH.

Hit the link and watch the video/check availability www.thecottagesonthekey.com/vacation-rentals/rental/latitude-adjustment-461/

03/21/2025

THE ABALAONE is the PERFECT vacation home for large groups on SIESTA KEY! Enjoy time with friends and family at this luxury duplex offering everything you would need to relax and rejuvenate! Separate living spaces (if required) and TWO pools surrounded by lush landscaping...PLUS steps away from Crescent Beach...

Memories made together last a lifetime...so book now - www.thecottagesonthekey.com/vacation-rentals/rental/the-abalone

Watch the video here https://youtu.be/uBh2ckaXCwk

03/20/2025

Imagine a vacay home just a 5-minute walk to the emerald waters of SIESTA KEY BEACH. BEACH WALK COTTAGE is a charming coastal haven in an old Florida style setting made for a true escape from everyday life.
Dog friendly too, what's not to ❤🐾?

Take a closer look here @ www.thecottagesonthekey.com/vacation-rentals/rental/beach-walk-cottage-451/

03/19/2025

Just in case you hadn't heard....SIESTA KEY BEACH NAMED #1 BEACH
Here's more about what makes this place so incredibly special.... and why visitors ❤ to stay with us....

03/18/2025

Beautiful DOG FRIENDLY 4-bedroom home on SIESTA KEY! Minutes to SHELL BEACH and a short car ride to SIESTA KEY VILLAGE!

Old Florida style with space that seamlessly flows indoors and outdoors to the pool and putting green. Fun for everyone!

Check availability here www.thecottagesonthekey.com/vacation-rentals/rental/siesta-dolce-3750/

03/17/2025

In the ♥️ of SIESTA KEY village, CJ's is THE perfect spot for the best of both worlds— fine white sand and crystal clear waters of SIESTA BEACH and the fun village vibe.
Six units - rent together for large parties OR individually. You choose!

Check availability @ https://www.thecottagesonthekey.com/vacation-rentals/rental/cjs-on-siesta/

Watch the video here https://youtu.be/7FEOeQXcCBc

03/16/2025

Do you dream of sunshine, soft sandy beaches, and crystal-clear waters of ANNA MARIA ISLAND? Mornings on the beach, afternoons exploring local treasures on Pine Avenue, or evenings under stunning sunsets, with Gulf views!
BENNYS BUNGALOW is a large seven-bedroom, seven-bathroom property ready to welcome you and your family and friends to this slice of paradise's serene beauty and laid-back charm.

Watch the video here @ https://youtu.be/rJ4h6QjYejc

are calling, so book your stay www.thecottagesonthekey.com/vacation-rentals/rental/bennys-bungalow-2213/

03/16/2025

Dreaming of sunshine, soft sandy beaches, and the crystal-clear waters of ANNA MARIA ISLAND?
Your island getaway awaits at BENNY'S BUNGALOW! Mornings spent exploring local treasures on Pine Avenue, a little beach time in the afternoon or evenings under stunning sunsets, with Gulf views!

This large seven-bedroom, seven-bathroom property is ready to welcome you, your family and friends back to this slice of paradise's serene beauty and laid-back charm.

Watch the video here @ https://youtu.be/rJ4h6QjYejc

The sunshine, soft sandy beaches, and crystal-clear waters are calling, so book your stay www.thecottagesonthekey.com/vacation-rentals/rental/bennys-bungalow-2213/

03/15/2025

The 45th Annual SARASOTA JAZZ FESTIVAL starts Monday, March 17th.
This SIX-DAY event will feature a variety of jazz performances and activities across multiple venues in downtown Sarasota....."jazz is a conversation, a give and take"

www.sarasotajazzfestival.com gives you all the info on performances, so make sure you get involved for the very best in Gulf Coast live jazz!

March 17-22, 2025Sarasota, Florida Music DirectorTerell Stafford Emmet Cohen Trio ⭑ Tony Monaco and Eric Alexander ⭑ Marcus Miller ⭑ Emmet Cohen Trio ⭑ Tony Monaco and Eric Alexander ⭑ Marcus Miller ⭑ Gustav Viehmeyer Trio The Thomas CarAbasiQuintet Gabrielle Cavassa MJR Latin Project TE...

03/14/2025

Looking to vacation with friends and family, but still need privacy when you want it? Check out SOL Y MAR, these two cozy coastal homes are your unique combo of side-by-side 2-bedroom, 1-bath units just a stone's throw from CRESCENT BEACH on beautiful SIESTA KEY.

Enjoy the private hot tub and large, beautifully maintained community pool or just steps from the beach for your daily dose of vitamin sea!

Follow the link to learn more and check availability https://www.thecottagesonthekey.com/vacation-rentals/rental/sol-y-mar/

03/13/2025

Decided where to enjoy the craic, and sip on a pint of Guinness this St Patrick's Day?
Here's a reminder of some of the best Irish Bars in the area! Slainte!

Raise a pint! These 10 Irish pubs in Sarasota, Bradenton, and Punta Gorda are great for St. Patrick’s Day — or any day you’re feeling lucky.

03/12/2025

Big Pass Hideaway’s private outdoor space is the perfect lush space to lounge or swim laps in the pool! Just steps away from Shell Beach; so relax and enjoy this 4 bedroom home offering comfort and luxury. Just a short hop to SIESTA VILLAGE too!

Check availability for your next Siesta Key vacation here www.thecottagesonthekey.com/vacation-rentals/rental/big-pass-hideaway-157/

Watch the video here https://youtu.be/eCQDhdQ1Z0Q