Family-Friendly Vacation Rentals in Siesta Key Village, FL: Compare 10+ Sites & Save

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1902 Best Family Vacation Rentals in Siesta Key Village (Starting from $301)

Luxe Lagoon - 119
Luxe Lagoon - 119
House
Siesta Key, FL, USA
0.1k from Siesta Key Village center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

7 Bedrooms22 Guests
New to Booking
$3260
Average price / night
Check Availability
Steps to Beach/Siesta Village-Resort Pool w/Slide
Steps to Beach/Siesta Village-Resort Pool w/Slide
House
Siesta Key, FL, 34242, United States
0.1k from Siesta Key Village center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub

7 Bedrooms18 Guests
10.0

Exceptional

41 reviews

$3041
Average price / night
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One-of-a-Kind! Pool, Terraces, Ocean-View Rooftop, in Siesta Village at Best Beach!
One-of-a-Kind! Pool, Terraces, Ocean-View Rooftop, in Siesta Village at Best Beach!
Apartment
Siesta Key, FL, USA
0.1k from Siesta Key Village center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Accessible hotels

4 Bedrooms13 Guests
New to Booking
$2844
Average price / night
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Private house steps from the beach and village.
Private house steps from the beach and village.
House
Siesta Key, FL, 34242, United States
0.1k from Siesta Key Village center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
6.6

Good

4 reviews

$781
Average price / night
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Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!
Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!
House
Siesta Key, FL, 34242, United States
0.1k from Siesta Key Village center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Extra Bed, Free Parking, Heater

4 Bedrooms13 Guests
10.0

Exceptional

46 reviews

$1575
Average price / night
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100 percent Private - Pool, Oceanviews, Village, Beaches!
100 percent Private - Pool, Oceanviews, Village, Beaches!
House
Siesta Key, FL, USA
0.1k from Siesta Key Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

8 Bedrooms26 Guests
New to Booking
$1710
Average price / night
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Siesta Key Beachside Villas
Siesta Key Beachside Villas
Villa
Siesta Key Village, Siesta Key, Florida, USA
0.1k from Siesta Key Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, 3-star, Lodgings, Vacation rentals

18 Bedrooms20 Guests
8.7

Fabulous

407 reviews

$1174
Average price / night
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Sports Lovers Dream - Steps to Beach - Gulf Views!
Sports Lovers Dream - Steps to Beach - Gulf Views!
House
Sarasota, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub

7 Bedrooms18 Guests
7.6

Good

4 reviews

$4248
Average price / night
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Summer House
Summer House
House
Siesta Key, FL, USA
0.1k from Siesta Key Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

6 Bedrooms22 Guests
New to Booking
$4101
Average price / night
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Cozy Coastal Getaway - 2 min Walk to Beach & Village, Shops & Restaurants
Cozy Coastal Getaway - 2 min Walk to Beach & Village, Shops & Restaurants
Apartment
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area

1 Bedroom4 Guests
10.0

Exceptional

23 reviews

$473
Average price / night
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Sunset Splash
Sunset Splash
House
Siesta Key, FL, USA
0.1k from Siesta Key Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

8 Bedrooms24 Guests
10.0

Exceptional

1 reviews

$2218
Average price / night
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Charming Chic Getaway - 2 min. Walk to Beach, Restaurants, & Shops
Charming Chic Getaway - 2 min. Walk to Beach, Restaurants, & Shops
Apartment
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

21 reviews

$445
Average price / night
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Southern Exposure
Southern Exposure
House
Siesta Key, FL, USA
0.1k from Siesta Key Village center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

5 Bedrooms13 Guests
10.0

Exceptional

3 reviews

$2572
Average price / night
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400ft to Beach, Ocean View, Pool, Rooftop, in the Siesta Key Village, 6-bdr
400ft to Beach, Ocean View, Pool, Rooftop, in the Siesta Key Village, 6-bdr
House
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking

6 Bedrooms16 Guests
10.0

Exceptional

2 reviews

$1872
Average price / night
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The Pool House
The Pool House
House
Siesta Key, FL, USA
0.1k from Siesta Key Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

5 Bedrooms16 Guests
New to Booking
$1794
Average price / night
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Gulf Views, Waterslide, Spa & Rooftop Lounge
Gulf Views, Waterslide, Spa & Rooftop Lounge
House
Sarasota, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub

6 Bedrooms16 Guests
8.0

Good

1 reviews

$3753
Average price / night
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Beachside of the Village By Beachside Management
Beachside of the Village By Beachside Management
Apartment
Siesta Key, FL, USA
0.2k from Siesta Key Village center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

2 Bedrooms4 Guests
9.5

Superb

4 reviews

$788
Average price / night
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Walk to Siesta Key Beach & Village | Private Patio | Prime Location!
Walk to Siesta Key Beach & Village | Private Patio | Prime Location!
Apartment
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
9.4

Superb

211 reviews

$449
Average price / night
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The Beachy Keen - U
The Beachy Keen - U
House
Siesta Key, FL, USA
0.2k from Siesta Key Village center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms10 Guests
New to Booking
$1644
Average price / night
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Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!
Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!
House
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms10 Guests
9.8

Exceptional

166 reviews

$904
Average price / night
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Sea Angel - 274
Sea Angel - 274
House
Siesta Key, FL, USA
0.2k from Siesta Key Village center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
9.0

Fabulous

3 reviews

$301
Average price / night
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Gertrudes Siesta Village Properties - short walk to Siesta's best beaches!
Gertrudes Siesta Village Properties - short walk to Siesta's best beaches!
House
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
9.4

Superb

3 reviews

$1467
Average price / night
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Gull Villa – Spacious 2BR, Walk to Siesta Key & Village, 1945 Triplex
Gull Villa – Spacious 2BR, Walk to Siesta Key & Village, 1945 Triplex
House
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms5 Guests
9.6

Exceptional

156 reviews

$373
Average price / night
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Walk to Siesta Key Beach & Village – Cozy 2BR , 1BA first floor
Walk to Siesta Key Beach & Village – Cozy 2BR , 1BA first floor
House
Sarasota, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.8

Exceptional

117 reviews

$372
Average price / night
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Steps to Siesta Key Beach & Village - 2BR w Balcony,   1945 Triplex 2nd Floor
Steps to Siesta Key Beach & Village - 2BR w Balcony, 1945 Triplex 2nd Floor
House
Siesta Key, FL, 34242, United States
0.2k from Siesta Key Village center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
9.6

Exceptional

123 reviews

$349
Average price / night
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Beachfront Luxury - Resort Pool - Steps to Village
Beachfront Luxury - Resort Pool - Steps to Village
House
Siesta Key, FL, 34242, United States
0.3k from Siesta Key Village center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub

5 Bedrooms12 Guests
10.0

Exceptional

9 reviews

$4602
Average price / night
Check Availability
Siesta Key Village pet friendly w heated pool & arcade. Short walk to the beach
Siesta Key Village pet friendly w heated pool & arcade. Short walk to the beach
Condo
Sarasota, FL, 34242, United States
0.3k from Siesta Key Village center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
9.2

Superb

12 reviews

$406
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Siesta Key Village.

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Siesta Key Village Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1902 verified family-friendly vacation rentals in Siesta Key Village. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Siesta Key Village vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $301 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Siesta Key Village offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Siesta Key Village are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Siesta Key Village often include amenities such as Child Friendly, Fireplace/Heating, and Guest Services. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.