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Montgomery Cottages - Vacation Rentals in Sarasota Springs

Charming tiny house with AC and WiFi in delightful Sarasota.Private and quiet. From US $99
         

8.0 (1 Review)
Cottage
Charming tiny house with AC and WiFi in delightful Sarasota.Private and quiet.
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Luxury Places to Stay in Sarasota Springs

Over 214+ Luxury Places to Stay in or Near Sarasota Springs
4BR/3.5 bath home, heated pool, game room, central SRQ-7 mil to Siesta Key Beach From US $817
         

9.8 (8 Reviews)
House
4BR/3.5 bath home, heated pool, game room, central SRQ-7 mil to Siesta Key Beach
  • Air Conditioner
  • Parking
  • Pool

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Family Vacation Home with Pool From US $690
         

9.0 (4 Reviews)
House
Family Vacation Home with Pool
  • Air Conditioner
  • Parking
  • Pool

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Tropical Family Retreat with Heated Pool, Jacuzzi, Mini Golf
New
From US $646
         

10.0 (1 Review)
House
Tropical Family Retreat with Heated Pool, Jacuzzi, Mini Golf
  • Air Conditioner
  • Parking
  • Pool

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Beautiful Oak View Manor - Siesta & Legacy Trail From US $601
         

New
House
Beautiful Oak View Manor - Siesta & Legacy Trail
  • Air Conditioner
  • Parking
  • Pool

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Mango Bay | Private Pool + Dog Play Area From US $597
         

2.0 (1 Review)
House
Mango Bay | Private Pool + Dog Play Area
  • Air Conditioner
  • Parking
  • Pet Friendly

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Serene Sarasota Retreat with King Bed, Full Kitchen, Fast Wi-Fi and A/C From US $559
         

New
House
Serene Sarasota Retreat with King Bed, Full Kitchen, Fast Wi-Fi and A/C
  • Air Conditioner
  • Parking
  • Pet Friendly

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Private Retreat! 3D Tour! New Hot Tub & Salt Water Pool! From US $550
         

10.0 (7 Reviews)
House
Private Retreat! 3D Tour! New Hot Tub & Salt Water Pool!
  • Air Conditioner
  • Parking
  • Pet Friendly

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3-Bedroom House Louxury.Heated Pool From US $541
         

New
House
3-Bedroom House Louxury.Heated Pool
  • Air Conditioner
  • Parking
  • Pool

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Top-Rated Vacation Rentals with a Pool in Sarasota Springs

Over 101+ Top-Rated Vacation Rentals with a Pool in or Near Sarasota Springs
Carlisle Inn From US $259
         

|
10.0 (2192 Reviews)
Hotel
Carlisle Inn
  • Air Conditioner
  • Parking
  • Pool

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Heated Private Pool! Recently Updated! Well Stocked Property! Mins to Beach From US $341
         

10.0 (47 Reviews)
House
Heated Private Pool! Recently Updated! Well Stocked Property! Mins to Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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Modern Oasis with Heated Pool near Siesta Key Beach and a Downtown 3BR/2BA From US $284
         

10.0 (45 Reviews)
House
Modern Oasis with Heated Pool near Siesta Key Beach and a Downtown 3BR/2BA
  • Air Conditioner
  • Parking
  • Pool

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Private heated pool home mins to beaches and down town Sarasota Pet friendly From US $303
         

10.0 (22 Reviews)
House
Private heated pool home mins to beaches and down town Sarasota Pet friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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Salt Life Villa with pool & outdoor dining From US $456
         

10.0 (8 Reviews)
House
Salt Life Villa with pool & outdoor dining
  • Air Conditioner
  • Pool
  • TV

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The Coral Cottage close to all that Sarasota has to offer From US $339
         

10.0 (6 Reviews)
House
The Coral Cottage close to all that Sarasota has to offer
  • Air Conditioner
  • Parking
  • Pool

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Dog-friendly pool home near beaches, shops, restaurants. From US $440
         

10.0 (3 Reviews)
House
Dog-friendly pool home near beaches, shops, restaurants.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Highland Cove Hideaway From US $328
         

|
10.0 (2 Reviews)
House
Highland Cove Hideaway
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Sarasota Springs

Over 63+ Pet-Friendly Vacation Rentals in or Near Sarasota Springs
Stunning Fully Remodeled House with Heated Pool! 30%OFF From US $244
         

9.2 (58 Reviews)
House
Stunning Fully Remodeled House with Heated Pool! 30%OFF
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Gray House Sarasota From US $221
         

|
9.7 (10 Reviews)
House
The Gray House Sarasota
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sunny 3BR Oasis Water View Beach Gear Fully Fenced Yard Near Siesta Key From US $227
         

10.0 (6 Reviews)
House
Sunny 3BR Oasis Water View Beach Gear Fully Fenced Yard Near Siesta Key
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cypress Inn - Modern home close to Siesta Key From US $393
         

10.0 (2 Reviews)
House
Cypress Inn - Modern home close to Siesta Key
  • Air Conditioner
  • Parking
  • Pet Friendly

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3 BR/3 BA with Private Pool & Patio Near Beaches From US $352
         

9.8 (68 Reviews)
House
3 BR/3 BA with Private Pool & Patio Near Beaches
  • Air Conditioner
  • Parking
  • Pet Friendly

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Coastal Pool Bungalow - 15 Mins to Famous Beaches From US $328
         

9.8 (30 Reviews)
House
Coastal Pool Bungalow - 15 Mins to Famous Beaches
  • Air Conditioner
  • Parking
  • Pet Friendly

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Your Dream Pool Home in Sarasota - #1 Siesta Key Beach a short drive From US $364
         

9.6 (82 Reviews)
House
Your Dream Pool Home in Sarasota - #1 Siesta Key Beach a short drive
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bamboo house From US $277
         

9.2 (37 Reviews)
House
Bamboo house
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Sarasota Springs

Over 16+ Large Vacation Homes & Villas in or Near Sarasota Springs
Sarasota's Family Friendly HEATED Pool Home Close to Siesta Key Beach From US $303
         

8.8 (5 Reviews)
House
Sarasota's Family Friendly HEATED Pool Home Close to Siesta Key Beach
  • Air Conditioner
  • Pet Friendly
  • Pool

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Sunny 3BR Oasis with Water View and Beach Gear Near Siesta From US $161
         

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New
House
Sunny 3BR Oasis with Water View and Beach Gear Near Siesta
  • Air Conditioner
  • Parking
  • Pet Friendly

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Siesta Key Family Getaway
New
From US $320
         

New
House
Siesta Key Family Getaway
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful, comfortable pool home 15 minutes from Famous Siesta Key Beach. From US $360
         

8.0 (2 Reviews)
House
Beautiful, comfortable pool home 15 minutes from Famous Siesta Key Beach.
  • Air Conditioner
  • Parking
  • Pool

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Very bright 3-bedroom pool villa, close to siesta Key beach From US $315
         

New
Villa
Very bright 3-bedroom pool villa, close to siesta Key beach
  • Air Conditioner
  • Parking
  • Pool

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Pet Friendly Tropical Villa, Heated Salt Pool From US $506
         

10.0 (3 Reviews)
Villa
Pet Friendly Tropical Villa, Heated Salt Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious Vacation Rental in Sarasota /Private Pool /Game Room with Pool Table From US $338
         

9.8 (20 Reviews)
House
Spacious Vacation Rental in Sarasota /Private Pool /Game Room with Pool Table
  • Air Conditioner
  • Parking
  • Pool

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Sun Tans & Fairways: Heated Pool and Hot Tub From US $399
         

9.6 (7 Reviews)
House
Sun Tans & Fairways: Heated Pool and Hot Tub
  • Air Conditioner
  • Pool
  • Balcony/Terrace

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Wheelchair Accessible Vacation Homes in Sarasota Springs

Over 5+ Wheelchair Accessible Vacation Homes in or Near Sarasota Springs
Pool, Sweet Pineapple From US $134
         

4.8 (12 Reviews)
House
Pool, Sweet Pineapple
  • Air Conditioner
  • Pool
  • TV

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Carlisle Inn Sarasota From US $413
         

|
9.5 (2088 Reviews)
Hotel
Carlisle Inn Sarasota
  • Air Conditioner
  • Parking
  • Pool

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Salt Life Villa - 3 bedroom 2 bathroom with heated POOL near beaches From US $275
         

4.8 (4 Reviews)
House
Salt Life Villa - 3 bedroom 2 bathroom with heated POOL near beaches
  • Air Conditioner
  • Pool
  • TV

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Private Pool, Sarasota, Bali Poolside From US $156
         

3.4 (5 Reviews)
House
Private Pool, Sarasota, Bali Poolside
  • Air Conditioner
  • Pool
  • TV

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Near Beach, Villa On Toucan From US $89
         

New
Condo
Near Beach, Villa On Toucan
  • Air Conditioner
  • Pet Friendly
  • TV

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Sarasota Springs Varoom and Airbnb Places to Stay Under $200

Over 59+ Sarasota Springs Varoom and Airbnb Places to Stay Under $200
Comfortable updated 3 bedroom home - enclosed, solar heated pool, private yard. From US $195
         

9.8 (50 Reviews)
House
Comfortable updated 3 bedroom home - enclosed, solar heated pool, private yard.
  • Air Conditioner
  • Parking
  • Pool

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Casa piscina cercana a playas y restaurantes From US $200
         

10.0 (2 Reviews)
House
Casa piscina cercana a playas y restaurantes
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Secret In the Springs Hideaway, a luxury efficiency at the Legacy Trail From US $88
         

10.0 (17 Reviews)
Apartment
The Secret In the Springs Hideaway, a luxury efficiency at the Legacy Trail
  • Air Conditioner
  • Parking
  • TV

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Cozy and Private Studio Retreat near Downtown & Beaches From US $113
         

10.0 (15 Reviews)
Apartment
Cozy and Private Studio Retreat near Downtown & Beaches
  • Air Conditioner
  • Parking
  • TV

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Pinecraft Paradise ~ Secluded Apt in central SRQ! From US $192
         

10.0 (14 Reviews)
Apartment
Pinecraft Paradise ~ Secluded Apt in central SRQ!
  • Air Conditioner
  • Parking
  • TV

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Centrally located Condo, Sarasota Fl 34232 From US $154
         

10.0 (1 Review)
Condo
Centrally located Condo, Sarasota Fl 34232
  • Air Conditioner
  • Pool
  • TV

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Single-story home with private yard, enclosed patio, updated interior, & W/D From US $141
         

9.0 (2 Reviews)
House
Single-story home with private yard, enclosed patio, updated interior, & W/D
  • Air Conditioner
  • Parking
  • TV

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Streamlined & Chic Getaway Studio in Amazing Sarasota From US $102
         

9.0 (2 Reviews)
Apartment
Streamlined & Chic Getaway Studio in Amazing Sarasota
  • Air Conditioner
  • Parking
  • Pet Friendly

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Instantly Bookable Vacation Homes in Sarasota Springs

Over 112+ Instantly Bookable Vacation Homes in or Near Sarasota Springs
Centrally Located, Sarasota Home Close To Amish Community From US $212
         

10.0 (172 Reviews)
House
Centrally Located, Sarasota Home Close To Amish Community
  • Air Conditioner
  • Parking
  • TV

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Riviera Retreat | Private Heated Pool + Infinity Game Table From US $341
         

New
House
Riviera Retreat | Private Heated Pool + Infinity Game Table
  • Air Conditioner
  • Parking
  • Pool

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Ingram House 2 From US $234
         

10.0 (58 Reviews)
House
Ingram House 2
  • Air Conditioner
  • Parking
  • TV

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Welcome to "Casa Amarilla"nn From US $477
         

10.0 (1 Review)
House
Welcome to "Casa Amarilla"nn
  • Air Conditioner
  • TV
  • Security/Safety

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Serene Pool Oasis w/put put golf in central location From US $360
         

10.0 (1 Review)
House
Serene Pool Oasis w/put put golf in central location
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Cheerful 3 Bedroom Home with Pool-No pets Please! From US $339
         

10.0 (1 Review)
House
Cheerful 3 Bedroom Home with Pool-No pets Please!
  • Air Conditioner
  • Parking
  • Pool

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Experience The Perfect Blend of Comfort & Convenience In This Charming Cozy Home From US $306
         

10.0 (1 Review)
House
Experience The Perfect Blend of Comfort & Convenience In This Charming Cozy Home
  • Air Conditioner
  • Parking
  • TV

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Sunshine beautiful house 3bed/2bath ,vacation rental From US $296
         

10.0 (1 Review)
House
Sunshine beautiful house 3bed/2bath ,vacation rental
  • Air Conditioner
  • Parking
  • TV

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About Sarasota Springs Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Sarasota Springs, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Sarasota Springs. Places to stay near Sarasota Springs with prices averaging $99 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Sarasota Springs with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Sarasota Springs

Type Count
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Sarasota Springs

★ Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sarasota Springs.

Weather in Sarasota Springs

View the weather forecast for Sarasota Springs before booking your Sarasota Springs Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

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