Family-Friendly Vacation Rentals in Historic Spanish Point, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida
  5.  Sarasota
  6.  Historic Spanish Point

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1095 Best Family Vacation Rentals in Historic Spanish Point (Starting from $130)

Windsor Lodge Unit 20, studio, 1BR 1BA close to the beaches, pool access
Windsor Lodge Unit 20, studio, 1BR 1BA close to the beaches, pool access
Apartment
Osprey, FL, USA
0.5k from Historic Spanish Point center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$176
Average price / night
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Windsor Lodge Unit #19, studio close to beaches
Windsor Lodge Unit #19, studio close to beaches
Apartment
Osprey, FL, 34229, United States
0.5k from Historic Spanish Point center

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

1 Bedroom4 Guests
New to Booking
$209
Average price / night
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Modern luxe getaway for families near Siesta Key
Modern luxe getaway for families near Siesta Key
House
Osprey, FL, USA
1.0k from Historic Spanish Point center

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

3 Bedrooms8 Guests
8.5

Very Good

2 reviews

$317
Average price / night
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Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
House
Osprey, FL, 34229, United States
1.0k from Historic Spanish Point center

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

3 Bedrooms6 Guests
9.8

Exceptional

12 reviews

$298
Average price / night
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Bay Acres Bungalow - B
Bay Acres Bungalow - B
House
Osprey, FL, USA
1.1k from Historic Spanish Point center

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

2 Bedrooms6 Guests
New to Booking
$288
Average price / night
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2-bedroom Spacious townhome in Osprey
2-bedroom Spacious townhome in Osprey
House
Osprey, FL, 34229, United States
2.0k from Historic Spanish Point center

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

2 Bedrooms5 Guests
10.0

Exceptional

17 reviews

$143
Average price / night
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Bay Acres Bungalow - A
Bay Acres Bungalow - A
Apartment
Osprey, FL, USA
1.1k from Historic Spanish Point center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay, Bungalows

2 Bedrooms6 Guests
New to Booking
$323
Average price / night
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☀Coastal Gem☀Heated pool & amazing location!☀
☀Coastal Gem☀Heated pool & amazing location!☀
House
Sarasota, FL, 34231, United States
2.0k from Historic Spanish Point center

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

2 Bedrooms6 Guests
9.8

Exceptional

8 reviews

$343
Average price / night
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Bay Acres Bungalow
Bay Acres Bungalow
House
Osprey, FL, USA
1.1k from Historic Spanish Point center

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

2 Bedrooms12 Guests
New to Booking
$543
Average price / night
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Villa in Osprey that sleeps the whole family
Villa in Osprey that sleeps the whole family
Apartment
Osprey, FL, 34229, United States
2.0k from Historic Spanish Point center

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

2 Bedrooms5 Guests
9.8

Exceptional

36 reviews

$130
Average price / night
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Pool, Hot tub, Close to Beaches, Shopping, More!
Pool, Hot tub, Close to Beaches, Shopping, More!
House
Historic Spanish Point, Osprey, Florida, USA
1.4k from Historic Spanish Point center

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

3 Bedrooms8 Guests
New to Booking
$425
Average price / night
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 Sarasota home in the Heart of the Gulfs most beautiful beaches.
Sarasota home in the Heart of the Gulfs most beautiful beaches.
House
Sarasota, FL, 34231, United States
2.1k from Historic Spanish Point center

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

3 Bedrooms6 Guests
10.0

Exceptional

30 reviews

$238
Average price / night
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Cute 3/2 Siesta home steps from Siesta waters
Cute 3/2 Siesta home steps from Siesta waters
House
Sarasota, FL, USA
2.2k from Historic Spanish Point center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$252
Average price / night
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Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
Condo
Osprey, FL, 34229, United States
2.2k from Historic Spanish Point center

AC, Balcony, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$136
Average price / night
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5 Mi to Beach Family Retreat in Sarasota!
5 Mi to Beach Family Retreat in Sarasota!
House
Sarasota, FL, USA
2.3k from Historic Spanish Point center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$177
Average price / night
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Idyllic Casey Key Beach House
Idyllic Casey Key Beach House
House
Osprey, FL, 34229, United States
2.2k from Historic Spanish Point center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.6

Exceptional

37 reviews

$685
Average price / night
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Sarasota - Dunmore 8730
Sarasota - Dunmore 8730
House
Sarasota, FL, USA
2.5k from Historic Spanish Point center

Guest Services, Security/Safety, Pool, Barbecue/Outdoor Cooking, Child Friendly

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$180
Average price / night
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Now available!!  Spacious Private home, near beaches and all!
Now available!! Spacious Private home, near beaches and all!
House
Sarasota, FL, 34231, United States
2.4k from Historic Spanish Point center

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

3 Bedrooms6 Guests
9.2

Superb

18 reviews

$417
Average price / night
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Turtle Bay Beauty
Turtle Bay Beauty
Apartment
Sarasota, FL, USA
2.6k from Historic Spanish Point center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay, Accessible hotels

2 Bedrooms4 Guests
New to Booking
$194
Average price / night
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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key
Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key
Condo
Siesta Key, FL, 34242, United States
2.5k from Historic Spanish Point center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
9.4

Superb

85 reviews

$313
Average price / night
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Tropical Shores Retreat-10 Min to Siesta Key Beach
Tropical Shores Retreat-10 Min to Siesta Key Beach
House
Sarasota, FL, USA
2.8k from Historic Spanish Point center

Air Conditioner, Parking, Security/Safety, Pet Friendly, Child Friendly

3 Bedrooms9 Guests
New to Booking
$292
Average price / night
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Fisherman's Cove - Gulf Front First Floor totally renovated with everything new
Fisherman's Cove - Gulf Front First Floor totally renovated with everything new
Condo
Sarasota, FL, 24242, United States
2.5k from Historic Spanish Point center

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

2 Bedrooms6 Guests
9.8

Exceptional

89 reviews

$360
Average price / night
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Siesta Keys Home with Deck Half Mile to Turtle Beach
Siesta Keys Home with Deck Half Mile to Turtle Beach
Apartment
Siesta Key, FL, USA
2.8k from Historic Spanish Point center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Beach rentals, Condos

2 Bedrooms4 Guests
New to Booking
$295
Average price / night
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Looking for the perfect vacation rental?
Looking for the perfect vacation rental?
Condo
Sarasota, FL, 34242, United States
2.5k from Historic Spanish Point center

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

2 Bedrooms4 Guests
9.8

Exceptional

33 reviews

$281
Average price / night
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Bayfront resort Condo, walk to Turtle Beach
Bayfront resort Condo, walk to Turtle Beach
Condo
Sarasota, FL, 34242, United States
2.5k from Historic Spanish Point center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$244
Average price / night
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Cozy canal front condo with heated pool walk to turtle beach
Cozy canal front condo with heated pool walk to turtle beach
Condo
Sarasota, FL, 34242, United States
2.5k from Historic Spanish Point center

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

1 Bedroom2 Guests
9.6

Exceptional

8 reviews

$256
Average price / night
Check Availability
Water Access Retreat | Kayaks + Hot Tub
Water Access Retreat | Kayaks + Hot Tub
House
Sarasota, FL, 34231, United States
2.6k from Historic Spanish Point center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
7.4

Good

3 reviews

$252
Average price / night
Check Availability

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 Historic Spanish Point.

Where to stay in Historic Spanish Point? Best neighborhoods & areas

Historic Spanish Point Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1095 verified family-friendly vacation rentals in Historic Spanish Point. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Historic Spanish Point vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $130 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Historic Spanish Point 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 Historic Spanish Point 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 Historic Spanish Point often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. 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.