Siesta Key 2BR Duplex • 3 Beds • Heated Pool
Entire condo in Siesta Key, Florida
- 6 guests ·
- · 2 bedrooms ·
- · 3 beds ·
- · 2.5 baths
Hosted by Scott
- 9 years hosting
Listing highlights
Self check-in
Check yourself in with the smartlock.
Extra spacious
Guests love this home’s spaciousness for a comfortable stay.
Garden and lake views
Soak up the views during your stay.
*JUNE 2026 Update*
Spacious 2BR duplex condo with 3 beds, perfect for families or small groups. The open living area features comfortable seating and an 55" HDTV, while each bedroom also includes its own HDTV. Stay connected with ultra-fast 500 Mbps Wi-Fi.
The fully equipped kitchen includes modern appliances, cookware, and dining space. Sleeping arrangements include a king size bed and 2 full beds, accommodating up to 6 guests in a clean, relaxing space designed for comfort and convenience.
The space
*JUNE 2026 Update*
Video of unit can be found on Youtube searching with the following code: jKmsmzQWmd8
Siesta Beach is TripAdvisor's No. 1 U.S. beach for 2026!
Siesta Key Beach Retreat • 2BR (3 bed, 2 1/2 bathroom) Duplex Condo • Heated Pool
Welcome to your perfect Siesta Key island escape—a bright and comfortable 2-bedroom, 3-bed duplex condo located inside the beautiful Bay Oaks community, one of the most peaceful and scenic spots on the island. Surrounded by mature oak trees, tropical landscaping, and waterfront views, this relaxing retreat offers the perfect balance of resort amenities, quiet island living and beach proximity (the public beach access points are a short walk down the street).
Whether you're planning a family beach vacation, couples getaway, or relaxing winter retreat, this condo gives you everything you need to experience the laid-back charm that makes Siesta Key one of the most loved beach destinations in the United States.
🏡 Comfortable Coastal Living
Inside the condo you’ll find a bright and welcoming coastal space designed for comfort after long days in the sun.
The open living area features comfortable seating, a 55" smart TV for streaming your favorite shows, and plenty of natural light and pool view lanai. The space flows into a fully equipped kitchen and dining area, making it easy to gather for meals, games, or planning your next beach adventure.
The condo comfortably sleeps up to six guests with a practical layout perfect for families or small groups.
Sleeping arrangements include:
• Primary bedroom with a comfortable King Size bed
• Second bedroom with 2 full-sized beds
• Spacious living area for relaxing after beach days
Both bedrooms have bathrooms/showers inside of the room.
With three total beds, everyone has space to unwind and recharge for the next day’s island adventures.
This is a 2nd floor unit (with both bedrooms on the 3rd floor) so you'll need to walk up a flight of 15 steps to reach the front door of the unit.
🏝 Resort-Style Amenities
Guests enjoy access to the Bay Oaks community amenities, which offer a true resort-style experience in a quiet tropical setting.
Amenities include:
• Heated resort-style swimming pool
• Private bayfront fishing pier perfect for sunrise views and dolphin sightings
• Tennis and pickleball courts
• BBQ and picnic areas
• Clubhouse with billiards and lounge space
• Beautiful walking paths shaded by large oak trees
The bayfront pier is one of the hidden gems of the property—many guests start their mornings here watching dolphins, manatees, and boats glide along the Intracoastal Waterway.
🏖 Minutes to the Beach
One of the best parts of this location is how easy it is to enjoy the beach.
You’re just a short, 5 minute walk or bike ride to Crescent Beach, famous for its calm turquoise water and soft white quartz sand. Siesta Key Beach—often ranked among the best beaches in the world—is also only minutes away.
Even better, the free Siesta Key trolley stops right outside the community, giving you easy access to:
• Siesta Key Beach
• Siesta Key Village restaurants and nightlife
• Local shops and boutiques
• Waterfront dining spots
You can explore the entire island without needing to drive.
🌅 The Perfect Island Location
Bay Oaks is loved by visitors because it offers peaceful tropical surroundings while still being close to everything.
Within minutes you’ll find:
• Beachfront restaurants and tiki bars
• Fresh seafood dining
• Kayak and paddleboard rentals
• Sunset cruises and dolphin tours
• Snorkeling at Point of Rocks
• Shopping and nightlife in Siesta Key Village
After a full day of island adventures, return to your quiet retreat to relax by the pool or enjoy a peaceful evening under the palms.
✨ Why Guests Love Staying Here
Guests consistently love this condo for its:
• Relaxing tropical atmosphere
• Spacious 2-bedroom layout with 3 beds
• Heated resort pool
• Beautiful bayfront fishing pier
• Walkable beach access
• Free island trolley convenience
Whether you're here to soak up the sun, explore the island, or simply relax in a tropical setting, this Siesta Key duplex condo offers the perfect home base for an unforgettable vacation.
Before booking, PLEASE ask me ANYTHING! I'm happy to address any questions and provide you a full list of my favorite things to do in and around Siesta Key so you can start planning your vacation immediately.
Guest access
Enjoy all of the following at the complex. A fishing pier, heated pool, waterfront grilling & picnic area, tennis & pickleball court, a bus stop for the free island shuttle, clubhouse with kitchen, pool table, lending library, assigned covered parking, covered bicycle parking, laundry facilities, 24hr video surveillance, and onsite property management. While we are directly across the street from Siesta Key Beach, unfortunately our condo does not have access to the private beach so you will need to enter through the public beach access points which are less than a 1/2 mile down the street in either direction. The free trolly stops right in front of our condo (tennis court) and will pick up/drop off throughout the day.
Other things to note
This property offers a higher quality than most rentals on Siesta Key. The kitchen is beautiful and the floor plan is very large. The location to the community pool and western views make this unit simply perfect.
Crib can be provided but request must be made during reservation process.
It is a duplex with the main (only) entrance up a flight of 15 steps. Once inside you'll be at the main living room/dining room/kitchen floor, both bedrooms are on the 2nd floor of the unit. Your private, covered parking spot is just a few feet from the front stairs.
All the beach essentials are available during your stay.
Tennis rackets/balls are also provided for use on the private court.
Pack 'n Play + High Chair are available for use in the closet.
3 HDTV's with YouTube TV (55" Living Room ; 43" in both bedrooms)
Upgraded to 500MB High Speed Internet
All Furnishings & Decor are New and Staged with a Bright and Fun Beach Vibe * Large Bedrooms and an Expansive Living Area Allow this Unit to Accommodate a Guest Count of 6 (Air mattress available in closet).
* Washer and Dryer Conveniently Located Inside the Unit * Wifi Available as Well for You and Your Family's Use * This Unit Has the Best Location of any in the Complex. Stepping Outside the Living Room and Master Suite onto the Lanai, You'll Love the Sweeping Views of the Siesta Key Sky and Full Views Looking Directly On top of the Community Pool * Nothing Could Be More Convenient and Valuable in Accommodating Your Stay in Paradise * This Property books Quickly!
The amazing amenities include access to a private fishing pier, private tennis court, billiard room, clubhouse, BBQ area, sauna, a heated swimming pool, plus it is a short distance from world-renowned Siesta Beach with its white, powder sand. Adorably furnished, 2nd floor unit centrally located overlooking the wonderful pool as you sit and relax on the 3 enclosed lanais.
Large Heated Pool (84 degrees) - Open 7am to 10pm.
Across the street from Siesta Beach with the public access points less than a 1/2 mile down the street. Free transportation with the free Siesta Key/Midnight Pass trolley stopping right in front of the condo complex by the tennis court.
This 2 Bedroom, 2.5 Bath Condo (1,200+ Sq Ft) Provides a Luxurious Environment for you and your family to enjoy while on Vacation.
It is a duplex with the main (only) entrance up a flight of stairs. Once inside, both bedrooms are on the 2nd floor of the unit. Your private, covered parking spot is just a few feet from the front stairs.
Exclusive Amenities Include:
• Lanai overlooking heated Community pool
• Fishing Pier and Dock
• Washer/Dryer
• Tennis Courts
• Clubhouse w/Barbecue Area
• Dining Table
• Secure Covered assigned parking space
• Fully-Stocked Kitchen
• Free Hi-Speed WIFI
• Free assigned covered parking space
Guest access
The pool has quiet hours - after 10PM which is a county rule. This complex closes the pool at that time. No motorcycles and trailers allowed on the complex grounds. One assigned parking space. There are some extra guest spots available with a required parking pass.
- This is an absolutely NO-pet property.
Approx drive times to airport and major attraction cities:
5 to 15 min - beaches, theater, restaurants, shopping, and more
20 min - SRQ Airport
30 min - Outlet mall
50 min - St Pete
60 min - TPA Airport/Port of Tampa
2hr - Disney World
Spacious 2BR duplex condo with 3 beds, perfect for families or small groups. The open living area features comfortable seating and an 55" HDTV, while each bedroom also includes its own HDTV. Stay connected with ultra-fast 500 Mbps Wi-Fi.
The fully equipped kitchen includes modern appliances, cookware, and dining space. Sleeping arrangements include a king size bed and 2 full beds, accommodating up to 6 guests in a clean, relaxing space designed for comfort and convenience.
The space
*JUNE 2026 Update*
Video of unit can be found on Youtube searching with the following code: jKmsmzQWmd8
Siesta Beach is TripAdvisor's No. 1 U.S. beach for 2026!
Siesta Key Beach Retreat • 2BR (3 bed, 2 1/2 bathroom) Duplex Condo • Heated Pool
Welcome to your perfect Siesta Key island escape—a bright and comfortable 2-bedroom, 3-bed duplex condo located inside the beautiful Bay Oaks community, one of the most peaceful and scenic spots on the island. Surrounded by mature oak trees, tropical landscaping, and waterfront views, this relaxing retreat offers the perfect balance of resort amenities, quiet island living and beach proximity (the public beach access points are a short walk down the street).
Whether you're planning a family beach vacation, couples getaway, or relaxing winter retreat, this condo gives you everything you need to experience the laid-back charm that makes Siesta Key one of the most loved beach destinations in the United States.
🏡 Comfortable Coastal Living
Inside the condo you’ll find a bright and welcoming coastal space designed for comfort after long days in the sun.
The open living area features comfortable seating, a 55" smart TV for streaming your favorite shows, and plenty of natural light and pool view lanai. The space flows into a fully equipped kitchen and dining area, making it easy to gather for meals, games, or planning your next beach adventure.
The condo comfortably sleeps up to six guests with a practical layout perfect for families or small groups.
Sleeping arrangements include:
• Primary bedroom with a comfortable King Size bed
• Second bedroom with 2 full-sized beds
• Spacious living area for relaxing after beach days
Both bedrooms have bathrooms/showers inside of the room.
With three total beds, everyone has space to unwind and recharge for the next day’s island adventures.
This is a 2nd floor unit (with both bedrooms on the 3rd floor) so you'll need to walk up a flight of 15 steps to reach the front door of the unit.
🏝 Resort-Style Amenities
Guests enjoy access to the Bay Oaks community amenities, which offer a true resort-style experience in a quiet tropical setting.
Amenities include:
• Heated resort-style swimming pool
• Private bayfront fishing pier perfect for sunrise views and dolphin sightings
• Tennis and pickleball courts
• BBQ and picnic areas
• Clubhouse with billiards and lounge space
• Beautiful walking paths shaded by large oak trees
The bayfront pier is one of the hidden gems of the property—many guests start their mornings here watching dolphins, manatees, and boats glide along the Intracoastal Waterway.
🏖 Minutes to the Beach
One of the best parts of this location is how easy it is to enjoy the beach.
You’re just a short, 5 minute walk or bike ride to Crescent Beach, famous for its calm turquoise water and soft white quartz sand. Siesta Key Beach—often ranked among the best beaches in the world—is also only minutes away.
Even better, the free Siesta Key trolley stops right outside the community, giving you easy access to:
• Siesta Key Beach
• Siesta Key Village restaurants and nightlife
• Local shops and boutiques
• Waterfront dining spots
You can explore the entire island without needing to drive.
🌅 The Perfect Island Location
Bay Oaks is loved by visitors because it offers peaceful tropical surroundings while still being close to everything.
Within minutes you’ll find:
• Beachfront restaurants and tiki bars
• Fresh seafood dining
• Kayak and paddleboard rentals
• Sunset cruises and dolphin tours
• Snorkeling at Point of Rocks
• Shopping and nightlife in Siesta Key Village
After a full day of island adventures, return to your quiet retreat to relax by the pool or enjoy a peaceful evening under the palms.
✨ Why Guests Love Staying Here
Guests consistently love this condo for its:
• Relaxing tropical atmosphere
• Spacious 2-bedroom layout with 3 beds
• Heated resort pool
• Beautiful bayfront fishing pier
• Walkable beach access
• Free island trolley convenience
Whether you're here to soak up the sun, explore the island, or simply relax in a tropical setting, this Siesta Key duplex condo offers the perfect home base for an unforgettable vacation.
Before booking, PLEASE ask me ANYTHING! I'm happy to address any questions and provide you a full list of my favorite things to do in and around Siesta Key so you can start planning your vacation immediately.
Guest access
Enjoy all of the following at the complex. A fishing pier, heated pool, waterfront grilling & picnic area, tennis & pickleball court, a bus stop for the free island shuttle, clubhouse with kitchen, pool table, lending library, assigned covered parking, covered bicycle parking, laundry facilities, 24hr video surveillance, and onsite property management. While we are directly across the street from Siesta Key Beach, unfortunately our condo does not have access to the private beach so you will need to enter through the public beach access points which are less than a 1/2 mile down the street in either direction. The free trolly stops right in front of our condo (tennis court) and will pick up/drop off throughout the day.
Other things to note
This property offers a higher quality than most rentals on Siesta Key. The kitchen is beautiful and the floor plan is very large. The location to the community pool and western views make this unit simply perfect.
Crib can be provided but request must be made during reservation process.
It is a duplex with the main (only) entrance up a flight of 15 steps. Once inside you'll be at the main living room/dining room/kitchen floor, both bedrooms are on the 2nd floor of the unit. Your private, covered parking spot is just a few feet from the front stairs.
All the beach essentials are available during your stay.
Tennis rackets/balls are also provided for use on the private court.
Pack 'n Play + High Chair are available for use in the closet.
3 HDTV's with YouTube TV (55" Living Room ; 43" in both bedrooms)
Upgraded to 500MB High Speed Internet
All Furnishings & Decor are New and Staged with a Bright and Fun Beach Vibe * Large Bedrooms and an Expansive Living Area Allow this Unit to Accommodate a Guest Count of 6 (Air mattress available in closet).
* Washer and Dryer Conveniently Located Inside the Unit * Wifi Available as Well for You and Your Family's Use * This Unit Has the Best Location of any in the Complex. Stepping Outside the Living Room and Master Suite onto the Lanai, You'll Love the Sweeping Views of the Siesta Key Sky and Full Views Looking Directly On top of the Community Pool * Nothing Could Be More Convenient and Valuable in Accommodating Your Stay in Paradise * This Property books Quickly!
The amazing amenities include access to a private fishing pier, private tennis court, billiard room, clubhouse, BBQ area, sauna, a heated swimming pool, plus it is a short distance from world-renowned Siesta Beach with its white, powder sand. Adorably furnished, 2nd floor unit centrally located overlooking the wonderful pool as you sit and relax on the 3 enclosed lanais.
Large Heated Pool (84 degrees) - Open 7am to 10pm.
Across the street from Siesta Beach with the public access points less than a 1/2 mile down the street. Free transportation with the free Siesta Key/Midnight Pass trolley stopping right in front of the condo complex by the tennis court.
This 2 Bedroom, 2.5 Bath Condo (1,200+ Sq Ft) Provides a Luxurious Environment for you and your family to enjoy while on Vacation.
It is a duplex with the main (only) entrance up a flight of stairs. Once inside, both bedrooms are on the 2nd floor of the unit. Your private, covered parking spot is just a few feet from the front stairs.
Exclusive Amenities Include:
• Lanai overlooking heated Community pool
• Fishing Pier and Dock
• Washer/Dryer
• Tennis Courts
• Clubhouse w/Barbecue Area
• Dining Table
• Secure Covered assigned parking space
• Fully-Stocked Kitchen
• Free Hi-Speed WIFI
• Free assigned covered parking space
Guest access
The pool has quiet hours - after 10PM which is a county rule. This complex closes the pool at that time. No motorcycles and trailers allowed on the complex grounds. One assigned parking space. There are some extra guest spots available with a required parking pass.
- This is an absolutely NO-pet property.
Approx drive times to airport and major attraction cities:
5 to 15 min - beaches, theater, restaurants, shopping, and more
20 min - SRQ Airport
30 min - Outlet mall
50 min - St Pete
60 min - TPA Airport/Port of Tampa
2hr - Disney World
Where you’ll sleep
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What this place offers
Courtyard view
Lake view
Waterfront
Kitchen
Fast wifi – 449 Mbps
Accessibility features
This info was provided by the Host and reviewed by Airbnb.
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4.62 out of 5 stars from 110 reviews4.62 · 110 reviews
Guest reviews mention
Where you’ll be
Siesta Key, Florida, United States
This listing's location is verified.
Neighborhood highlights
Across the street from the #1 Beach in the U.S.
Siesta Key Beach is commonly rated the # 1 beach in the United States for good reason! With its soft, powdery white sand, huge 8-mile stretch of beach, and constant activity in and around Siesta Key itself, there are many reasons to fall in love with Siesta Key.
Things to do "in and around" Siesta Key:
Siesta Key Family Vacation: Best Time to Visit
The beauty of Siesta Key is that it can be enjoyed year-round and is visited by thousands of vacation-goers throughout every season.
With temperatures averaging around 70 degrees, many people love to visit Siesta Key in the fall, winter, and spring months. The mild, comfortable temperatures and predictable weather make this a great time to enjoy the beaches, watersports, and other Siesta Key activities.
For those looking to get away during the summer months, Siesta Key offers the same great attractions but with higher temperatures and humidity levels.
Temperatures range in the 80s and 90s from June – September, making these both the hottest months, as well as the most ideal months to swim in the gulf.
The following Siesta Key family vacation itinerary can be executed and enjoyed regardless of what month you plan to visit!
Siesta Key Family Vacation: Day 1
Arrive in Siesta Key, Florida
Check-in to your Siesta Key unit and
head to Siesta Key Village and explore options on where to reserve your weekly beach rentals
Walk down Ocean Boulevard to window shop and find stores or boutiques that pique your interest
Have dinner at The Old Salty Dog in Siesta Key Village
Arrival
We never recommend planning too much to do on the first day of a family vacation. Arrival day (Day 1) should consist of checking-in to the unit and getting acquainted with your immediate surroundings.
Get to know the local area before venturing out to explore and experience the sights and attractions that draw you away from your overnight accommodations.
Determine where you will get your morning breakfast and coffee. Are there late-night bars and restaurants nearby? Do you have access to the amenities that you’ll need throughout the week?
Finally, check out the onsite pool, bayside pier, or nearby beach and park trails in order to establish what to do during your downtime, and where to get in your daily exercise.
Siesta Key Village
In addition to its famous beaches, Siesta Key Village is the heart of any Siesta Key family vacation! For this reason, getting to know your way around Siesta Key Village is recommended on the first day of your Siesta Key itinerary.
Siesta Key Village is a hub of beachy bars, restaurants, shops, as well as (beach and land) sport rental outfitters located in the center of the island, only a few blocks away from the ocean.
Apart from the condo and beautiful surroundings, the majority of your vacation will be spent in Siesta Key Village when not at the beach.
Additional planning tip: The main street in Siesta Key Village is Ocean Boulevard.
All of the restaurants and bars mentioned in this Siesta Key itinerary are located within the city blocks of Siesta Key Village on or around the main street.
Siesta Key Family Vacation: Day 2
Take a morning walk to Meaney’s Mini Donuts in Siesta Key Village
Check out week-long bike, beach chair, and beach umbrella rentals from Robinhood Rentals (or the business of your choice)
Grab your beach essentials and spend the day at Siesta Key Beach
Enjoy “Big G’s Happy Hour”, live music, and dinner at Siesta Key Oyster Bar
Watch the sunset at Sunset Point (Siesta Key Beach Access #2)
Siesta Key Beach
The highlight of Day 2 of your Siesta Key family vacation is spending the day at world-famous Siesta Key Beach!
Siesta Key Beach, also known as Siesta Beach, is the most popular beach in Siesta Key, Florida. Likewise, it was rated the #1 beach in America by TripAdvisor users in 2015, 2017 and 2020.
The sugary-white sand found here is literally out-of-this-world amazing and is what draws families and vacation-goers here year-after-year.
The full line-up of amenities offered at Siesta Key Public Beach include:
First aid center with lifeguards on duty year-round
Public restrooms and showers
800 car public parking lot
Full-service snack bar and gift shop
Picnic areas with and without cover
Gazebos and shelters that can accommodate 60-120 people.
Families can also enjoy all the following sporting activities at Siesta Key Beach:
Playground equipment
A tennis court complex
Volleyball courts
A 20 station fitness trail
Sunset Point
Another one of the most popular things to do on the island of Siesta Key is to watch the sunset!
Since the island of Siesta Key faces West out into the Gulf of Mexico, you’re always guaranteed a front-row seat to watch the sun sink below the horizon.
Though there are many places to catch a sunset on Siesta Key, the best lookout point is at Sunset Point.
Located at the north end of Siesta Key Public Beach, this jut of land offers one of the best views of the magnificently lit evening skies.
Though you can see gorgeous sunsets anywhere along Crescent and Siesta Key Beach, Sunset Point is a fun gathering spot where many other tourists come together each evening.
In fact, you may find yourself returning here every night of your Siesta Key family vacation!
Additional planning tip: Keep a close eye out, for there’s a possibility that you’ll catch a rare sight known as a “green flash”. The green flash is a quick spot of green seen at the top of the sinking sun.
Siesta Key Family Vacation: Day 3
Take a morning beach walk and collect shells
Head to Siesta Key Watersports and grab a half-day (4 hr.) boat rental; Cruise around the Gulf of Mexico and hang out at Big Pass Sandbar
Stick around Siesta Key Watersports and take guided parasailing adventure ($85 per person)
Get freshened up and head into Siesta Key Village for dinner and drinks on the patio at The Hub Baja Grill
Siesta Key Water Rentals
Day 3 of this Siesta Key family vacation itinerary involves getting out to enjoy and explore the Gulf of Mexico via watersport rentals.
Popular watersport activities in Siesta Key include kayaking, parasailing, jet-skiing, and boating.
No need to look too far, because Siesta Key is home to several watersport outfitters that have ample equipment and guides to make for the perfect ocean outing!
Because Siesta Key Watersports (outfitters) offers both boat rentals and parasailing, we recommend using their combined services on this day during your Siesta Key family vacation.
Other Siesta Key water sport rentals are listed here:
Siesta Key Aqua Adventures – Banana boat and aqua spinner rides
Parasail Siesta – Parasailing ($90/flyer) and boat rentals
CB’s Saltwater Outfitters – Jet ski and boat rentals
Siesta Key Jet Ski – Jet ski rentals
Robinhood Rentals – Paddleboard and kayak rentals
Siesta Paddlesports – Paddleboard and kayak rentals
Siesta Key Paddleboards – Paddleboard rentals
Siesta Key Family Vacation: Day 4
Enjoy breakfast and coffee at Another Broken Egg restaurant
Relax on Crescent Beach and go snorkeling at Point of Rocks
Return to your beach-side accommodations to freshen up
Rent an electric scooter or scooter car from Ride & Paddle and cruise around the island
Have dinner at the Lobster Pot Restaurant
End the day with drinks and live music on the Daiquiri Deck
Crescent Beach at Siesta Key
After dinings at Siesta Key’s most popular breakfast hang out, Another Broken Egg, get ready for an ultra-relaxing day by heading to Crescent Beach.
Crescent Beach is the most private, non-private beach in Siesta Key and is quieter and more secluded than its counterpart, Siesta Key Beach.
This part of the Siesta Key is an enclave where the beach is densely lined with condos, villas, and vacation rentals that provide direct access to the waterfront.
Midnight Pass Road provides the only (easy to miss) public access to enter Crescent Beach. From there, there’s a 25-space parking lot and walking pathway that leads out onto the beach.
Though it doesn’t have the same amenities as Siesta Beach, you can still go shelling, build sandcastles, and enjoy the ocean with a bit more privacy.
In addition, Siesta Key’s diving and snorkeling hotspot called Point of Rocks is located at the southern tip of Crescent Beach. This is where you’ll spend the next hour or so during this itinerary.
Siesta Key’s Point of Rocks
Though a bit difficult to get to, the Point of Rocks is known as the best place to snorkel in Siesta Key. It is also one of the best family activities in Siesta Key.
The easiest way to find Point of Rocks is to walk to the southern-most end of Crescent Beach until you reach a gigantic sea wall. You must then climb along the sea wall, turn a corner, and walk down 3 steps into the water.
By now you will see the amazing tide pools and snorkeling area complete with an array of gigantic moss-covered rocks that protrude from the ocean.
The water is no more than 5 feet deep here, and there is a vast amount of and marine life that includes fish, crabs, and red sponge.
The shallow water makes this a perfect place for kids/beginners to snorkel with a basic retail store snorkeling set.
There are also large distributions of seashells, making this a perfect spot for shell picking.
Additional planning tips: Wear water shoes when visiting Point of Rocks as the terrain is made up of crushed shells and coral. Also, the rocks can get quite slippery.
There are only 10 – 12 parking spots at the alley access for Point of Rocks. This is why it is best to park at Crescent Beach and walk from there.
Siesta Key Family Vacation: Day 5
Get coffee and crepes at Bonjour French Cafe’
Take a 2 hour Dolphin and Sea Life Tour from Siesta Key Marina
Drive 15 miles South to visit the “Shark Tooth Capital of the World”, Venice Beach, Florida
Shop through downtown Venice. Spend time at Venice Beach and end your day with dinner and drinks at Sharky’s On The Pier
Siesta Key Dolphin Cruise
Start the day off with delicious croissants, homemade crepes, fresh-squeezed orange juice and specialty coffees at Siesta Key Village’s Boujour French Cafe!
Next, spend the morning of Day 5 taking an unforgettable guided dolphin cruise!
By far one of the best things to do in Siesta Key is to watch dolphins jump and play in their natural environment on a guided dolphin cruise!
Siesta Key waters are home to one of the largest populations of wild bottlenose dolphins. Seeing dolphins in their natural habitat is both thrilling and serene, as well as something that you will never forget.
The beauty of taking a guided dolphin cruise is that the captain of the boat knows where to find them and will provide you with a relaxing experience to get a first-hand view.
Siesta Key dolphin cruises vary in length, time of day, and overall experience. We chose Siesta Key Marina for their wide variety of dolphin cruises available, as well as their family-friendly atmosphere.
Venice Beach
We absolutely loved our afternoon trip to Venice Beach in Venice Beach, FL! This is why we recommend that you include a stop here in your Siesta Key family vacation!
Venice Beach is unique in that is has a high density of fossilized shark teeth that can be found ashore. There are also many opportunities to see wild dolphins here.
In addition, the beaches along Venice are home to a large number of marine turtle nests. These can be found between the months of May and October.
Last, the perfect place to enjoy appetizers, dinner, and a drink is at tourist hotspot, Sharky’s on the Pier!
Sharky’s is located right on Venice Beach with direct views of both the beach and fishing pier. There is indoor and outdoor seating, a gift shop, and a super fun and laid back tropical vibe.
Siesta Key Family Vacation: Day 6
Drive 7 miles North to Sarasota, Florida
Stop to take photos at the Unconditional Surrender Sculpture
Visit the Circus Museum at The Ringling
Take a 2 hour guided kayak tour through the Sarasota mangroves with I Kayak Sarasota
Spend time at Lido Beach
Browse, shop, and dine at Lido Key’s St. Armands Circle
To cap off your amazing Siesta Key family vacation, considering venturing out a bit more to explore the surrounding communities of Sarasota and Lido Key, Florida.
Along with soaking up the sun along additional white-sand beaches, treat yourself to diverse dining, museums and culture, and various shopping districts found in these awesome Florida communities.
Siesta Key Family Vacation: Getting There
Siesta Key is an 8-mile barrier island. The island is 11 miles (a 20-minute drive) from Sarasota-Bradenton International Airport and 71 miles (a 90-minute drive) from Tampa International Airport.
Siesta Key Beach is commonly rated the # 1 beach in the United States for good reason! With its soft, powdery white sand, huge 8-mile stretch of beach, and constant activity in and around Siesta Key itself, there are many reasons to fall in love with Siesta Key.
Things to do "in and around" Siesta Key:
Siesta Key Family Vacation: Best Time to Visit
The beauty of Siesta Key is that it can be enjoyed year-round and is visited by thousands of vacation-goers throughout every season.
With temperatures averaging around 70 degrees, many people love to visit Siesta Key in the fall, winter, and spring months. The mild, comfortable temperatures and predictable weather make this a great time to enjoy the beaches, watersports, and other Siesta Key activities.
For those looking to get away during the summer months, Siesta Key offers the same great attractions but with higher temperatures and humidity levels.
Temperatures range in the 80s and 90s from June – September, making these both the hottest months, as well as the most ideal months to swim in the gulf.
The following Siesta Key family vacation itinerary can be executed and enjoyed regardless of what month you plan to visit!
Siesta Key Family Vacation: Day 1
Arrive in Siesta Key, Florida
Check-in to your Siesta Key unit and
head to Siesta Key Village and explore options on where to reserve your weekly beach rentals
Walk down Ocean Boulevard to window shop and find stores or boutiques that pique your interest
Have dinner at The Old Salty Dog in Siesta Key Village
Arrival
We never recommend planning too much to do on the first day of a family vacation. Arrival day (Day 1) should consist of checking-in to the unit and getting acquainted with your immediate surroundings.
Get to know the local area before venturing out to explore and experience the sights and attractions that draw you away from your overnight accommodations.
Determine where you will get your morning breakfast and coffee. Are there late-night bars and restaurants nearby? Do you have access to the amenities that you’ll need throughout the week?
Finally, check out the onsite pool, bayside pier, or nearby beach and park trails in order to establish what to do during your downtime, and where to get in your daily exercise.
Siesta Key Village
In addition to its famous beaches, Siesta Key Village is the heart of any Siesta Key family vacation! For this reason, getting to know your way around Siesta Key Village is recommended on the first day of your Siesta Key itinerary.
Siesta Key Village is a hub of beachy bars, restaurants, shops, as well as (beach and land) sport rental outfitters located in the center of the island, only a few blocks away from the ocean.
Apart from the condo and beautiful surroundings, the majority of your vacation will be spent in Siesta Key Village when not at the beach.
Additional planning tip: The main street in Siesta Key Village is Ocean Boulevard.
All of the restaurants and bars mentioned in this Siesta Key itinerary are located within the city blocks of Siesta Key Village on or around the main street.
Siesta Key Family Vacation: Day 2
Take a morning walk to Meaney’s Mini Donuts in Siesta Key Village
Check out week-long bike, beach chair, and beach umbrella rentals from Robinhood Rentals (or the business of your choice)
Grab your beach essentials and spend the day at Siesta Key Beach
Enjoy “Big G’s Happy Hour”, live music, and dinner at Siesta Key Oyster Bar
Watch the sunset at Sunset Point (Siesta Key Beach Access #2)
Siesta Key Beach
The highlight of Day 2 of your Siesta Key family vacation is spending the day at world-famous Siesta Key Beach!
Siesta Key Beach, also known as Siesta Beach, is the most popular beach in Siesta Key, Florida. Likewise, it was rated the #1 beach in America by TripAdvisor users in 2015, 2017 and 2020.
The sugary-white sand found here is literally out-of-this-world amazing and is what draws families and vacation-goers here year-after-year.
The full line-up of amenities offered at Siesta Key Public Beach include:
First aid center with lifeguards on duty year-round
Public restrooms and showers
800 car public parking lot
Full-service snack bar and gift shop
Picnic areas with and without cover
Gazebos and shelters that can accommodate 60-120 people.
Families can also enjoy all the following sporting activities at Siesta Key Beach:
Playground equipment
A tennis court complex
Volleyball courts
A 20 station fitness trail
Sunset Point
Another one of the most popular things to do on the island of Siesta Key is to watch the sunset!
Since the island of Siesta Key faces West out into the Gulf of Mexico, you’re always guaranteed a front-row seat to watch the sun sink below the horizon.
Though there are many places to catch a sunset on Siesta Key, the best lookout point is at Sunset Point.
Located at the north end of Siesta Key Public Beach, this jut of land offers one of the best views of the magnificently lit evening skies.
Though you can see gorgeous sunsets anywhere along Crescent and Siesta Key Beach, Sunset Point is a fun gathering spot where many other tourists come together each evening.
In fact, you may find yourself returning here every night of your Siesta Key family vacation!
Additional planning tip: Keep a close eye out, for there’s a possibility that you’ll catch a rare sight known as a “green flash”. The green flash is a quick spot of green seen at the top of the sinking sun.
Siesta Key Family Vacation: Day 3
Take a morning beach walk and collect shells
Head to Siesta Key Watersports and grab a half-day (4 hr.) boat rental; Cruise around the Gulf of Mexico and hang out at Big Pass Sandbar
Stick around Siesta Key Watersports and take guided parasailing adventure ($85 per person)
Get freshened up and head into Siesta Key Village for dinner and drinks on the patio at The Hub Baja Grill
Siesta Key Water Rentals
Day 3 of this Siesta Key family vacation itinerary involves getting out to enjoy and explore the Gulf of Mexico via watersport rentals.
Popular watersport activities in Siesta Key include kayaking, parasailing, jet-skiing, and boating.
No need to look too far, because Siesta Key is home to several watersport outfitters that have ample equipment and guides to make for the perfect ocean outing!
Because Siesta Key Watersports (outfitters) offers both boat rentals and parasailing, we recommend using their combined services on this day during your Siesta Key family vacation.
Other Siesta Key water sport rentals are listed here:
Siesta Key Aqua Adventures – Banana boat and aqua spinner rides
Parasail Siesta – Parasailing ($90/flyer) and boat rentals
CB’s Saltwater Outfitters – Jet ski and boat rentals
Siesta Key Jet Ski – Jet ski rentals
Robinhood Rentals – Paddleboard and kayak rentals
Siesta Paddlesports – Paddleboard and kayak rentals
Siesta Key Paddleboards – Paddleboard rentals
Siesta Key Family Vacation: Day 4
Enjoy breakfast and coffee at Another Broken Egg restaurant
Relax on Crescent Beach and go snorkeling at Point of Rocks
Return to your beach-side accommodations to freshen up
Rent an electric scooter or scooter car from Ride & Paddle and cruise around the island
Have dinner at the Lobster Pot Restaurant
End the day with drinks and live music on the Daiquiri Deck
Crescent Beach at Siesta Key
After dinings at Siesta Key’s most popular breakfast hang out, Another Broken Egg, get ready for an ultra-relaxing day by heading to Crescent Beach.
Crescent Beach is the most private, non-private beach in Siesta Key and is quieter and more secluded than its counterpart, Siesta Key Beach.
This part of the Siesta Key is an enclave where the beach is densely lined with condos, villas, and vacation rentals that provide direct access to the waterfront.
Midnight Pass Road provides the only (easy to miss) public access to enter Crescent Beach. From there, there’s a 25-space parking lot and walking pathway that leads out onto the beach.
Though it doesn’t have the same amenities as Siesta Beach, you can still go shelling, build sandcastles, and enjoy the ocean with a bit more privacy.
In addition, Siesta Key’s diving and snorkeling hotspot called Point of Rocks is located at the southern tip of Crescent Beach. This is where you’ll spend the next hour or so during this itinerary.
Siesta Key’s Point of Rocks
Though a bit difficult to get to, the Point of Rocks is known as the best place to snorkel in Siesta Key. It is also one of the best family activities in Siesta Key.
The easiest way to find Point of Rocks is to walk to the southern-most end of Crescent Beach until you reach a gigantic sea wall. You must then climb along the sea wall, turn a corner, and walk down 3 steps into the water.
By now you will see the amazing tide pools and snorkeling area complete with an array of gigantic moss-covered rocks that protrude from the ocean.
The water is no more than 5 feet deep here, and there is a vast amount of and marine life that includes fish, crabs, and red sponge.
The shallow water makes this a perfect place for kids/beginners to snorkel with a basic retail store snorkeling set.
There are also large distributions of seashells, making this a perfect spot for shell picking.
Additional planning tips: Wear water shoes when visiting Point of Rocks as the terrain is made up of crushed shells and coral. Also, the rocks can get quite slippery.
There are only 10 – 12 parking spots at the alley access for Point of Rocks. This is why it is best to park at Crescent Beach and walk from there.
Siesta Key Family Vacation: Day 5
Get coffee and crepes at Bonjour French Cafe’
Take a 2 hour Dolphin and Sea Life Tour from Siesta Key Marina
Drive 15 miles South to visit the “Shark Tooth Capital of the World”, Venice Beach, Florida
Shop through downtown Venice. Spend time at Venice Beach and end your day with dinner and drinks at Sharky’s On The Pier
Siesta Key Dolphin Cruise
Start the day off with delicious croissants, homemade crepes, fresh-squeezed orange juice and specialty coffees at Siesta Key Village’s Boujour French Cafe!
Next, spend the morning of Day 5 taking an unforgettable guided dolphin cruise!
By far one of the best things to do in Siesta Key is to watch dolphins jump and play in their natural environment on a guided dolphin cruise!
Siesta Key waters are home to one of the largest populations of wild bottlenose dolphins. Seeing dolphins in their natural habitat is both thrilling and serene, as well as something that you will never forget.
The beauty of taking a guided dolphin cruise is that the captain of the boat knows where to find them and will provide you with a relaxing experience to get a first-hand view.
Siesta Key dolphin cruises vary in length, time of day, and overall experience. We chose Siesta Key Marina for their wide variety of dolphin cruises available, as well as their family-friendly atmosphere.
Venice Beach
We absolutely loved our afternoon trip to Venice Beach in Venice Beach, FL! This is why we recommend that you include a stop here in your Siesta Key family vacation!
Venice Beach is unique in that is has a high density of fossilized shark teeth that can be found ashore. There are also many opportunities to see wild dolphins here.
In addition, the beaches along Venice are home to a large number of marine turtle nests. These can be found between the months of May and October.
Last, the perfect place to enjoy appetizers, dinner, and a drink is at tourist hotspot, Sharky’s on the Pier!
Sharky’s is located right on Venice Beach with direct views of both the beach and fishing pier. There is indoor and outdoor seating, a gift shop, and a super fun and laid back tropical vibe.
Siesta Key Family Vacation: Day 6
Drive 7 miles North to Sarasota, Florida
Stop to take photos at the Unconditional Surrender Sculpture
Visit the Circus Museum at The Ringling
Take a 2 hour guided kayak tour through the Sarasota mangroves with I Kayak Sarasota
Spend time at Lido Beach
Browse, shop, and dine at Lido Key’s St. Armands Circle
To cap off your amazing Siesta Key family vacation, considering venturing out a bit more to explore the surrounding communities of Sarasota and Lido Key, Florida.
Along with soaking up the sun along additional white-sand beaches, treat yourself to diverse dining, museums and culture, and various shopping districts found in these awesome Florida communities.
Siesta Key Family Vacation: Getting There
Siesta Key is an 8-mile barrier island. The island is 11 miles (a 20-minute drive) from Sarasota-Bradenton International Airport and 71 miles (a 90-minute drive) from Tampa International Airport.
Meet your host
Lives in New York, New York
I'm from New York City and purchased these properties as I've always been impressed with Siesta Key and the Gulf Coast atmosphere. Owning a few pieces of paradise became a priority and I am now proud to share those experiences with you.
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Checkout before 10:00 AM
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