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

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

Nightly prices starting at
Siesta Key holiday rentals start at $101 NZD per night before taxes and fees

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

Pet-friendly accommodation
Find 310 rentals that welcome pets

Holiday 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 holiday 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.

Tiki Bar Paradise! Heated Pool & Gaming Oasis!
Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.
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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
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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.
FamilyIndoor spacesBiking

Heated Pools & Spa · Private Beach + Bay Views
Perfect for family and group beach stays, with reliable Wi-Fi and a dedicated workspace for flexible remote work. This oversized renovated 2‑bed, 2‑bath condo sleeps six: a king in the master and two queens in the second bedroom; both bathrooms serve the group for privacy and convenience. Enjoy full gulf-to-bay living with private beach access and supplied chairs, umbrella, cooler and wagon, plus two heated pools, a heated spa, gym, courts, bay views, free parking and keypad self check-in.
FamilyIndoor spacesRiver

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.
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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.
KitchenFamilyParking

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!
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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!
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Heated pool & Infrared Sauna, 2 min to beach
Our 3-story home offers privacy for multiple families and is just 1 mile from Siesta Key Beach. Call the free shuttle for a quick ride to the Village for shopping and dining. Enjoy TVs in every bedroom, a full kitchen, laundry room, infrared sauna, and beach chairs. Two bedrooms have private baths. Relax in the heated pool and covered outdoor dining area while watching the game, surrounded by palm trees and salty air. SunfishBeachSiesta awaits!
Indoor spacesFamilyQuiet

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!
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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.
Indoor spacesKitchenAccess

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴
FamilyIndoor spacesBackyard
Popular amenities for Siesta Key family-friendly rentals
Family-friendly home rentals with a hot tub

Sun-filled cottage with pool, walk to beach
Indoor spacesKitchenBarbecue

Beachfront Siesta Key | Gulf View + Private Beach
Indoor spacesKitchenWi-Fi

LJ's Cottage 2
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Relax+ Jacuzzi | 9 Min to Siesta Key Beach
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Siesta Key For Me @ The Palm Bay Club
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Quaint Cottage,150 steps away from Crescent Beach!
Indoor spacesFamilyCleanliness

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
Indoor spacesKitchenCheckout

Summer Vibes*HTD Pool*Hot Tub*Fire Pit*Game Room
FamilyIndoor spacesNearby
Family- and pet-friendly home rentals

Beachy Cottage close to Siesta | 3 Bed | Huge Pool
KitchenFamilyComfort

Siesta Key, FL - Casa Berano
KitchenFamilyCheckout

Heart of Village: Dog-Friendly w/ Pool & Parking
Indoor spacesFamilyCheckout

5213A Calle Menorca - Siesta Key Village Condo
Indoor spacesKitchenLaundry

Beechwood Suites B
Indoor spacesKitchenLong stay

Siesta Key Quaint Beach House
KitchenFamilyAccuracy

Siesta Beach View : Pineapple Bungalow Efficiency
KitchenFamilyLocation

Oasis by Siesta Key Beach and Downtown SRQ w/pool
Indoor spacesKitchenWalkability
Family-friendly home rentals with a pool

Siesta Beach House
Indoor spacesKitchenGetting around

Beachwalk Townhouse with view of Gulf of Mexico
KitchenIndoor spacesAir conditioning

Sarasota Surf & Racquet Club Siesta Key Condo
Indoor spacesFamilyCheckout

Crystal House on Siesta Key Beach
KitchenFamilyComfort

Beachfront Getaway in Siesta Key
Indoor spacesFamilyQuiet

Island Time!
Indoor spacesKitchenLong stay

Steps to Siesta Key Beach! Sunset Balcony Views!
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Siesta Key House, Pool & Hot Tub, 1 mile to beach
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When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $540 NZD | $675 NZD | $736 NZD | $592 NZD | $504 NZD | $518 NZD | $460 NZD | $418 NZD | $375 NZD | $399 NZD | $463 NZD | $501 NZD |
| 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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- Family-friendly rentals Sarasota County
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- Anna Maria Island
- Siesta Beach
- Anna Maria Island Beach
- Raymond James Stadium
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
- Manasota Key Beach
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- John's Pass
- Tropicana Field
- Englewood Beach
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- Img Academy
- River Strand Golf and Country Club
- Splash Harbour Water Park
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