
Longboat Key long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Longboat Key. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Longboat Key are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Longboat Key
Showing deals for:8 Feb - 8 Mar
Image gallery for Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees
Sarasota
Image gallery for Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA

Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
Sarasota
Image gallery for LUXURIOUS VILLA WATERFRONT NEAR SIESTA KEY BEACH

LUXURIOUS VILLA WATERFRONT NEAR SIESTA KEY BEACH
Sarasota
Image gallery for 1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ

1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ
Sarasota
Image gallery for Luxury 6BR Retreat with Beach Access

Luxury 6BR Retreat with Beach Access
Siesta Key
Image gallery for Tropical Shores Retreat-Great Location - Discounts for stays 3 months or longer

Tropical Shores Retreat-Great Location - Discounts for stays 3 months or longer
Sarasota
Image gallery for 3 miles to Siesta Key, Screened in Lanai, 3 Bedrooms, Walking dist to Publix

3 miles to Siesta Key, Screened in Lanai, 3 Bedrooms, Walking dist to Publix
Sarasota
Image gallery for Walk to the Beach! Luxury 4 BR 5 BA Retreat on Siesta Key on Grand Canal Near Village

Walk to the Beach! Luxury 4 BR 5 BA Retreat on Siesta Key on Grand Canal Near Village
Siesta Key
Image gallery for 4BR Family Backyard w/ Pickleball, Pool, Playset, Hot Tub, Mini Golf, Fire pit

4BR Family Backyard w/ Pickleball, Pool, Playset, Hot Tub, Mini Golf, Fire pit
Bradenton
Image gallery for Free Heated Pool, Baby Gear, Shuffleboard, EV charger, Near beach, UTC mall, SRQ

Free Heated Pool, Baby Gear, Shuffleboard, EV charger, Near beach, UTC mall, SRQ
Sarasota
Image gallery for Free Heated Pool, 2 miles to IMG, Arcade + Mini Putt, Pets, Close to 4 beaches

Free Heated Pool, 2 miles to IMG, Arcade + Mini Putt, Pets, Close to 4 beaches
Bradenton
Image gallery for BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Sarasota
Image gallery for Sunny Family Home Near IMG & Anna Maria: Dedicated Workspace

Sunny Family Home Near IMG & Anna Maria: Dedicated Workspace
Bradenton
Image gallery for Heated saltwater pool + bubbling hot tub + cozy massage chair

Heated saltwater pool + bubbling hot tub + cozy massage chair
Bradenton
Image gallery for Family - HotTub - Sauna - Pickleball - Game Room

Family - HotTub - Sauna - Pickleball - Game Room
Bradenton
Image gallery for 3-bedroom house, Luxury Remodel, 5 Mins to #1 Siesta Key Beaches, Close to all!

3-bedroom house, Luxury Remodel, 5 Mins to #1 Siesta Key Beaches, Close to all!
Sarasota
Image gallery for Downtown Sarasota Florida Vacation Rental, Pet-Friendly 3BR/2BA,Close to Beaches

Downtown Sarasota Florida Vacation Rental, Pet-Friendly 3BR/2BA,Close to Beaches
Sarasota
Image gallery for Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Bradenton
Image gallery for Quiet Waterview Oasis - 10 minutes to Anna Maria Island

Quiet Waterview Oasis - 10 minutes to Anna Maria Island
Bradenton
Image gallery for Pet-Friendly 1BR Sarasota Florida Vacation Rental, Patio, Near Beaches, 2 Guests

Pet-Friendly 1BR Sarasota Florida Vacation Rental, Patio, Near Beaches, 2 Guests
Sarasota
Image gallery for Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach

Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach
Sarasota
Image gallery for Centrally Located Charming Beach Suite in Sarasota

Centrally Located Charming Beach Suite in Sarasota
Sarasota
Image gallery for NEW Casa Tropicana Siesta Key Luxury Hot Tub Saltwater Pool Cabana Private Yard

NEW Casa Tropicana Siesta Key Luxury Hot Tub Saltwater Pool Cabana Private Yard
Siesta Key
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Longboat Key
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Longboat Key Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Longboat Key come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Longboat Key
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Longboat Key with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Longboat Key
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Longboat Key with flexible cancellation policies.