The Best Vacation Rentals to Book in Sarasota, Florida

Poolside relaxation awaits at the Esplanade by Siesta Key
Poolside relaxation awaits at the Esplanade by Siesta Key | Courtesy of Esplanade by Siesta Key / Expedia
Photo of Nick Dauk
15 December 2021
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Sarasota is a happy medium between the metropolitan city of Tampa and the beachside bliss of Venice, and remarkable sunsets are seen from these shores every night. The city has all of the hip cuisine, galleries and boutiques you want, while a 10-minute drive will take you to local haunts where there’s hardly a snowbird in sight. Check it all out from the comfort of one of these great vacation homes in Sarasota, bookable with Culture Trip.

Tropical Waterview Mansion, for easy access to attractions

Pool at the Tropical Waterview Mansion, next to a pond
Courtesy of Tropical Waterview Mansion / Expedia

Let this one-bedroom Sarasota vacation home with water views give you whatever Florida vacation you crave. With a handy location right off of I-75, day trips to Disney and Naples are as easy as spending all afternoon in your private pool. Ease yourself into the low-key lifestyle with a drive over to Siesta Key for the sunset and into St Armands Circle for a lively evening of car shows and wine tasting. Did we mention a driving range is close by, too?

Esplanade by Siesta Key, for an extended vacation

Living room at the Esplanade by Siesta Key with grey decor
Courtesy of Esplanade by Siesta Key / Expedia
Resort-style amenities plus a short drive to the beach equals a Sarasota vacation home that you don’t want to miss out on. Condos here are available for a minimum of one month’s rental, meaning you’ve got at least a four-week holiday to see and do it all. Your first stop – outside of the resort-style pool, pickleball court and Bahama Bar, of course – should be the popular Siesta Key Beach, where the lively locals will show you how to adapt to South Florida living.

White Pine Court, for golfing access

Large bedroom at the White Pine Court
Courtesy of White Pine Court / Booking.com
All you need to know about this two-bedroom, two-bathroom condo is that it’s got enough room for your foursome and your clubs. The kitchen, the patio and access to the fitness center at the complex are all secondary bits of info. Even Sarasota Square, only 12 minutes by foot, isn’t your top priority. Stoneybrook Golf & Country Club is less than 3mi (4.8km) away, so we doubt you’ll have the time or energy to take aim at the tennis courts.

Mahogany Run Condo, for outdoor exploits in Myakka River State Park

Outdoor pools at the Mahogany Run Condo
Courtesy of Mahogany Run Condo / Booking.com
Visiting the beach is not obligatory when staying at this Sarasota holiday rental. You and your crew can lounge all day at this two-bedroom condo, doing nothing more than shooting the breeze on the balcony and rock-paper-scissoring who gets to use the spa tub. When the call of the wild sends you outside, the Myakka River State Park is 10 minutes away to give you hours of hiking, biking and wildlife viewing.

Island Dreams Cozy Cottage #4, for lazy beach days

Living and dining room at the Island Dreams Cozy Cottage #4, decorated in light colors
Courtesy of Island Dreams Cozy Cottage #4 / Booking.com
So close to the beach that it might as well be your living room, this one-bedroom cottage was built for beach bums. Ideal for a couple on a getaway or a solo trip with your best furry friend, the small kitchen and cozy outdoor patio are more than space to wind down with wine. Any spot on Lido Key Beach is perfect for suntanning, but there’s just something about the Manatee Jetty that makes it the right place for sunset viewing.

Casa Sea Esta, for sightseeing

Suite at the Casa Sea Esta, with a double bed and armchairs
Courtesy of Casa Sea Esta / Expedia
Get that hotel vibe from a Sarasota vacation home in this close-to-the-coast apartment. A private pool, fitness center and game room are all yours to hang out in when you’re not discovering Downtown. The Classic Car Museum and the Ringling Museum are minutes away, but the beach will take another few miles to reach. Anna Maria Island is well worth the half-hour haul if remarkable sunsets and amazing seafood are your idea of a good holiday.

Happy Gecko, for suburban tranquility

Modern apartment at the Happy Gecko, with a separate kitchen and living room
Courtesy of Happy Gecko / Booking.com
A quiet holiday home in Sarasota located within a residential area – this is where the real Florida lifestyle can be experienced. It’s choosing to lounge by the pool instead of making the 2.5mi (4km) drive to the beach (because the sand isn’t going anywhere). It’s not having to worry about cooking lunch for three bedrooms’ worth of family members because a Publix sub – a Florida delicacy – is always a crowd-pleaser.

Lido Dream Getaway Duplex S, for water sports galore

Dark-brown kitchen at the Lido Dream Getaway Duplex S
Courtesy of Lido Dream Getaway Duplex S / Booking.com
Walk to St Armands Circle for fine dining – or ice cream – from this dreamy duplex on Lido Key. Two bedrooms and two bathrooms are plenty for your small family. Park your car in the garage, and leave it there for days at a time. The beach is a shorter walk than the circle, making it effortless to flip-flop the kids back home for a backyard barbecue. As an added perk, this Sarasota holiday rental includes free admission to Xplorie’s bike, kayak and dolphin cruise rentals.

Village des Pins 3645 by Vtrips, for use of a community hot tub

Veranda with wicker chairs at the Village des Pins 3645 by Vtrips
Courtesy of Village des Pins 3645 by Vtrips / Booking.com
Here’s a secret about home rentals in Sarasota: the south is a quieter slice of paradise. This two-bedroom home proves it with a screened-in patio and a community hot tub that you can use as often as you please. Siesta Key and Downtown are close, but fewer crowds will be found at Turtle Beach, which is half the distance and a mere 15-minute drive away and offers the same immaculate sunsets, best viewed from a paddleboard.

Pelican Gardens Villa, for easy sea access

Dining room with a large ceiling at Pelican Gardens Villa
Courtesy of Pelican Gardens Villa / Booking.com
The kids won’t mind sharing a sofa bed at Pelican Gardens Villa. As it’s only footsteps to South Lido Park – where you’ll find nature trails and mangrove tunnels – they’ll be ready and rearing to get out into the Hansen Bayou before you can hit the snooze button on the alarm clock. This coastal, cream-colored one-bedroom condo is on Lido Key, conveniently equidistant from kayaking with the kids on the Big Sarasota Pass and sipping a cocktail at the Tiki Bar when the little ones hit the hay.

Visiting Sarasota with your pet? Check out our pick of the best pet-friendly hotels in Sarasota, Florida, bookable on Culture Trip. For more hotel options, check out our pick of the best hotels in Sarasota, Florida, for every traveler, bookable on Culture Trip.

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