
Family-friendly vacation rentals in Siesta Key
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Siesta Key

Total vacation rentals
Explore 1,820 vacation rentals in Siesta Key

Nightly prices starting at
Siesta Key vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

Verified guest reviews
Over 27,090 verified reviews to help you choose

Pet-friendly vacation rentals
Find 310 rentals that welcome pets

Vacation rentals with a pool
1,530 properties feature pools

Rentals with dedicated workspaces
830 properties have a dedicated workspace

Wi-Fi availability
1,800 of Siesta Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Siesta Key rentals

4.8 Average rating
Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Siesta Key
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!
KitchenFamilyWalkability

Beachwalk Townhouse with view of Gulf of Mexico
Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.
Indoor spacesFamilyLocation

Modern 4BR Home *Heated Pool & Spa*
Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265
Indoor spacesKitchenHospitality

Comfy Siesta Key Condo
Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.
FamilyKitchenWalkability

Beachfront Siesta Key | Gulf View + Private Beach
Sun Bum Studio is your Siesta Key Beachfront Escape Wake up steps from the white quartz sand of world-famous Siesta Key. Sun Bum Studio is located in the beachfront tower at Palm Bay Club, with a south-facing view of the beach and Gulf from the floor-to-ceiling glass doors and patio. Enjoy private Crescent Beach access with complimentary beach loungers, two heated pools, hot tub, fitness center, tennis and pickleball courts, fishing pier, boat docks, grills and free covered parking.
KitchenFamilyNearby

The Flamingo's Nest at Sea Club II
The Flamingo's Nest at Sea Club II features a beautiful new pool on the intracoastal waterway, a tiki hut for on-site cocktail hours, a plethora of boats and sea birds to enjoy while cooking on our new charcoal grills, a fishing pier, boat basin, and private beach access directly across the street. We are located 1.5 miles from the Village, loaded with amazing shops, restaurants, and night life. Condo remodeled top to bottom in 2019. Beach towels, chairs, and accessories provided.
KitchenIndoor spacesAccess

Siesta Key Beach & Village 2BR/2BA Steps to Beach
This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located in the heart of Siesta Key Village. You will be within a 2 minute walk to Siesta Key Beach and Siesta Village. With a beach house décor and equipped with 3 smart TVs, WIFI, cable, refrigerator, microwave, W/D, grill, beach chairs, toys for the kids, beach wagon, 1 queen bed, 2 twin beds and sleeper queen sofa. This private beach home has everything you need for a beach vacation. Local ownership.
FamilyIndoor spacesNearby

Cottage on Siesta Key Beachside & Stunning sunsets
Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!
KitchenIndoor spacesAir conditioning

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
A spacious and quiet 2-floor, 2 bedroom, 2.5 bathroom condo that lives like home and is close to everything Siesta Key offers. Spread out and enjoy YOUR vacation! Your condo features large rooms, comfy and modern surroundings, (2) Master Bedrooms upstairs, and you are steps away from a gorgeous heated pool that you can view from your lanai. This is the perfect condo for you and your family to relax in and simply enjoy your time in Siesta Key!
Indoor spacesKitchenAccuracy

Siesta Key Escape | 2BR + Den | Pool & Gulf Views
Cozy Coastal Getaway 🌊 Beautifully updated 2BR + den, 2BA apartment (1,200 sqft) on the first floor with 2 private balconies and partial Gulf views from the den. Sleeps 6 guests max (King, 2 Twins, Queen in den). Stay cool with central AC and ceiling fans in every bedroom and the kitchen. Enjoy a full kitchen, washer/dryer, 2 TVs, and a heated lagoon-style pool shared by just two duplexes—your perfect Siesta Key retreat!
FamilyKitchenComfort

Siesta Key Beach Front Condo
Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.
FamilyIndoor spacesLayout

Last MIN AUG Sarasota #1 Luxury Villa! PRIV BEACH!
BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!
Indoor spacesKitchenNearby
Popular amenities for Siesta Key family-friendly rentals
Family-friendly home rentals with a pool

Heated pool & Infrared Sauna, 2 min to beach
KitchenFamilyBeach

Tiki Bar Paradise! Heated Pool & Gaming Oasis!
FamilyKitchenTV

Heated Pools & Spa · Private Beach + Bay Views
KitchenIndoor spacesLaundry

Sun-filled cottage with pool, walk to beach
KitchenIndoor spacesAmenities

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Indoor spacesFamilyPool

Beachfront Getaway in Siesta Key
KitchenIndoor spacesQuiet

Siesta Key, FL - Casa Berano
Indoor spacesKitchenNearby

Island Time!
KitchenIndoor spacesLayout
Family-friendly home rentals with air conditioning

Siesta Key Village Home
KitchenIndoor spacesDecor

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
KitchenFamilyBeach

Sun Coast Oasis-Heated Pool-Pool Table-Arcade
FamilyIndoor spacesComfort

Beachfront 180-Degree View, Walk to Village!
FamilyIndoor spacesCondition

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
Indoor spacesFamilyValue

Luxury 3B/3B waterfront home w/ pool + boat access
Indoor spacesFamilyLocation

Siesta Key Home | Heated Pool, Theater & Arcade
KitchenFamilyQuiet

Siesta Key Retreat 1mi to Beach!
FamilyKitchenWalkability
Family-friendly home rentals with Wifi

Modern Home Heated Pool near Siesta & Downtown
KitchenFamilyCheck-in

Sunny & Comfy ~ Steps to Siesta Key Beach ~ Pool!
Indoor spacesFamilyGetting around

Amazing beach view! Entire unit renovated!
KitchenIndoor spacesBeach

Siesta Bliss ~ Luxury Waterfront Retreat
FamilyIndoor spacesBackyard

Siesta Key Beach front 2 bedroom condo w/ parking
FamilyKitchenValue

Walk To Siesta Key Beach & Village ; Renovated 2BR
KitchenFamilyLaundry

Gulf and Beach Views-Steps from Beach and Village
FamilyIndoor spacesCleanliness

Siesta Key Luxury Penthouse, walk to Beach&Village
Indoor spacesFamilyCheck-in
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,172 | ﺩ.ﺇ 1,465 | ﺩ.ﺇ 1,598 | ﺩ.ﺇ 1,285 | ﺩ.ﺇ 1,094 | ﺩ.ﺇ 1,124 | ﺩ.ﺇ 999 | ﺩ.ﺇ 907 | ﺩ.ﺇ 815 | ﺩ.ﺇ 867 | ﺩ.ﺇ 1,006 | ﺩ.ﺇ 1,087 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
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