Vacation rentals with a pool in Whitfield

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Top-rated rentals with a pool in Whitfield

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Guest favorite

Home in Sarasota

4.9 out of 5 average rating, 107 reviews

🌴🐬Bay Haven- Resort style Backyard 🏊‍♀️🔥 & Game Rm⚽️

Welcome to "The Bay Haven" - a family friendly vacation villa with a view of Sarasota Bay! Relax in our luxurious 2350 sq. ft. single-level home boasting an open floor plan and a 600 sq. ft. rec room stocked with family games & entertainment. The home is fully remodeled with high-end finishes and designer touches. Enjoy the backyard oasis, including a large heated pool, firepit, plenty of seating and a grill. It’s an easy drive to the white sand beaches of Siesta Key and Anna Maria Island.

Nov 22 – 29

ﺩ.ﺇ3,552 per night

Guest favorite

Guest suite in Sarasota

4.89 out of 5 average rating, 110 reviews

Downtown privacy, beaches and nightlife all around

For the couple (or individual) who wants a fabulous private home and is in a centrally-located space in downtown Sarasota. Where the beaches meet the nightlife (Legacy Trail is 5 short blocks away, pickle ball 3 and Robarts Arena 2), this separate In-Law Suite has its own entrance, private patio and lots of space (1,000 sq. feet). 2 bikes and beach items for use are: chairs, umbrellas, noodles and coolers. The washer/dryer is attached, high-speed internet/cable; there is a gas grill, 2 tvs

Jul 19 – 26

ﺩ.ﺇ460 per night

Guest favorite

Home in Sarasota

4.93 out of 5 average rating, 29 reviews

Heated Pool near Downtown, SRQ, Lido Key Beach!

Don't miss out on this impeccable maintained POOL HOME located in Whitfield Estates! Ideally located just 7 miles from downtown Sarasota, 7 miles from Downtown Bradenton, only 15 minutes to UTC and UTC Mall! Take a walk over to the historic Sara Bay Country Club, with easy access to The Ringling Museum and School of Art and Design, University of South Florida, and Asolo Repertory Theatre. All of that AND just a short drive away from beautiful beaches - 8mi to Lido Beach and 13mi to Siesta Key!

Nov 13 – 20

ﺩ.ﺇ1,098 per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 13 reviews

Waterfront Suite-20 min to Gulf Beaches

A hidden gem awaits you in this waterfront “Old Florida” style guest suite. You’ll be in a separate suite with your own entrance, bedroom & cozy living area. The setting offers amazing days swimming in the pool, paddle boarding, fishing or boating. Maybe you’ll see manatees in the creek or the ducks, turtles, our cats & resident Blue Heron parade around the property. Beach lovers can get to the gorgeous gulf beaches of AMI in about 20 minutes. Nightlife? We’re 15 min from downtown Sarasota.

Oct 13 – 20

ﺩ.ﺇ475 per night

Guest favorite

Condo in Bradenton

4.94 out of 5 average rating, 108 reviews

Newly remodeled cozy 2 bed/2.5 bath townhome

Fully renovated 2 bedroom/2.5 bathroom townhome nestled in a quiet, gated community in Bradenton between I-75 and some of the best beaches in the country. My townhome features 2 bedrooms (queen size) with en suite bathrooms. Beds are queen size. Amenities in the neighborhood include: large heated pool, tennis and basketball courts, playground, volleyball area, sport field, and designated parking spot steps away from the front door. Non-numbered guest parking is also available.

Nov 26 – Dec 3

ﺩ.ﺇ638 per night

Guest favorite

Guesthouse in Sarasota

5.0 out of 5 average rating, 102 reviews

Magical Guesthouse 1 mi from SRQ airport

Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Aug 28 – Sep 4

ﺩ.ﺇ651 per night

Guest favorite

Guesthouse in Sarasota

4.89 out of 5 average rating, 168 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

Jul 7 – 14

ﺩ.ﺇ481 per night

Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 103 reviews

The Seabreeze Cottage with peaceful water views

Welcome to my newly renovated townhouse! The Seabreeze Cottage is a two bedroom, 1.5 bath, colorfully decorated townhouse with a fun beachy vibe! It has beautiful and peaceful water views of the lake. It’s within 30 minutes of the Gulf Coast’s best beaches, including Anna Maria Island, Longboat Key, and Siesta Key. Only ten miles from Sarasota airport (SRQ) and about one hour from Tampa airport (TPA). It’s just 7 miles or 15 min from the world renowned IMG Academy.

Dec 19 – 26

ﺩ.ﺇ722 per night

Superhost

Home in Sarasota

4.84 out of 5 average rating, 135 reviews

☀ Pet and Family Friendly Home with Pool ☀

Our spacious single-level house is perfect for families as it comfortably sleeps 10 people. The home features a renovated caged pool, an outdoor seating area with a BBQ grill, three 4K smart TVs, a game room and a fire pit. The backyard is fenced and well-behaved dogs are welcome. We are a short drive away from some of the best beaches in the country, amazing kayaking, bike riding and hiking trails. The pool can be heated up to 78-82F for an extra charge ($25/day).

Jun 15 – 22

ﺩ.ﺇ1,158 per night

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 131 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

Aug 13 – 20

ﺩ.ﺇ487 per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 188 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Jul 20 – 27

ﺩ.ﺇ408 per night

Guest favorite

Home in Sarasota

4.85 out of 5 average rating, 150 reviews

The Sea is Calling

Our home, The Sea is Calling, is located on a cul de sac in Whitfield Estates. It is a short drive to many world class beaches and attractions like Lido Beach, Siesta Key, Longboat Key, Mote Marine, Ringling Museum and Sarasota Jungle Gardens. Our home is welcoming and we hope you decide to let us share a bit of paradise with you. When The Sea is Calling, you must go! We hope to see you soon.

Apr 22 – 29

ﺩ.ﺇ860 per night