Longboat Key, Sarasota Vacation & Condo Rentals

Longboat Key Apartment 10.0

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.
Beautifully remodeled and upgraded; .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Apartment 9.6

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.
A first floor 2 bedroom 2 bath condo that offers a view o.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Apartment 9.8

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 1-Queen Bed, 1-Sofa Sleeper
Situated in this idyllic resort compri.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 10.0

. The condo is situated in one of the most beautiful Beachfront Properties in Longboat Key. The lush landscape along with the ammenities that Beachplace has to offer makes you feel like you are staying in paradise........read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.6

The view is amazing! The condo overlooks the pristine white sand beach and has a beautiful Gulf view. This second floor gulf front condo has a heated pool and a tennis court. This remodeled condo is furnished to an exceptional contemporary standard, with travertine flooring throughout, new beds, furniture and appliances (bluetooth wireless Bose box.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo

Spacious 2 bedroom condo in Beachplace gated complex. King in Master bedroom. Come enjoy your time at the Beach. This is a great condo for you to call home for a month or more. Condo is meticulously clean and well cared for. Owners have upgraded the furnishings including large smart TV's One month Minimum.

The well-maintained and gor.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Villa 9.8

Newly remodeled charming 2 bed/ 1 bath condo located 5 min walk from beach, restaurants, groceries and more. Perfect place for a relaxing beach getaway!

Nestled in a quiet residential complex and centrally located in Longboat key, condo features a fully equipped renewed kitchen with upgraded brand-new stainless-steel appliances, new quartz .......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Longboat Key Condo 10.0

A very warm welcome to your beautiful, home away from home on this Island Paradise!

This gorgeous location is truly one of the most relaxing places on the planet, and we know that you are just going to love it!

With views of the gorgeous Gulf of Mexico from the living areas, Master Bedroom and Lanai of our fabulous first floor apartm.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.8

Our condo has everything you will need for a relaxing vacation on the beach.

The island of Longboat Key...
... is one of the most beautiful places in Florida. Longboat was voted the second most favored island in North America, according to a survey by a nationally recognized travel magazine. Daytime excursions are numerous, so that you.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.6

Offered by FL Vacation Connection, this perfect island getaway is located on the southern tip of Longboat Key with a beautiful beach and pool area.
This deluxe unit features almost 1700 sq ft with a 52’ long, beachfront lanai. The oversized living and dining area and both bedrooms open to the lanai. There is a fully equipped kitchen with micr.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Condo

Immerse yourself in this beautiful 2 bedroom, 2 bathroom condo just steps away from one of the most beautiful beaches in Florida. Fully furnished and tastefully decorated, this slice of paradise will make you feel right at home on Longboat Key. The original artwork that adorns the walls of this vacation home - created by recognized painters, LED-li.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Private vacation home 10.0

THIS PROPERTY HAS BEEN INSPECTED BY AND REGISTERED WITH THE TOWN OF LONGBOAT KEY RRR# 00134.2023

*****ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT****PLEASE PROVIDE DETAILED DESCRIPTION OF TRAVELERS WHEN REQUESTING A BOOKING ****

The Pineapple Cottage is a special oasis of tranquility and comfort. Surrounded by the pa.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.8

Two minute walk to Private Gulf Beach access, no need to cross the street.

This charming unit is the only 2 bedroom ground floor unit in Cabana Beach Club, a secluded, tropical, boutique resort that has all of the amenities for a Romantic Getaway or Family Vacation.

The private patio has an umbrella table and chairs for comfortable o.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.8

Welcome to our Ground floor BEACHFRONT condo unit #119 at the beautiful Sand Cay Beach Resort on Longboat Key!

Magnificent renovated (January 2022) condo with an open 1,132 sq. ft. floor plan, 2 bedrooms, 2 full bathrooms, full kitchen, a large living and dining room as well as a separate sitting room with a queen sleeper sofa. Condo sleeps .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Private vacation home 8.0

Enjoy the complete island experience in this 2-story two bedroom, one and a half bath, canal front condo, with boat docking. The kitchen and bathrooms were fully remodeled in 2023! We're located on a quiet street in close proximity to Sarasota Bay, with direct bay access, and next to Joan Durante Park with 32 acres of trails, boardwalks and preserv.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Condo

Great beach and Gulf views are breathtaking from your balcony, living room, kitchen and dining room of the Penthouse condo located on the 15th floor of Islands West Complex. You will love the beach views and fast Wi-Fi. Master bedroom with King bed has amazing views of the Bay and the Sarasota Downtown Skyline . The second bedroom has a double b.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Condo 9.0

Enjoy your morning coffee on your spacious, open-air, Gulf view Balcony overlooking your included beach and swimming pool facilities at the Exclusive Resort at Longboat Key Club. This booking does not include use of private club facilities such as golf and tennis or restaurants, etc.. Condo has a maximum occupancy of five people, to include maxim.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Longboat Key Condo 9.2

Second floor,.. It's very cozy with all the comforts of home. This renovated unit has an updated kitchen and baths with new ceramic tile. New furniture through out with a flat screen television. Complete beach supplies, toys and umbrellas. Unit sleeps a max of 6 people: 1 queen, 2 twins, 1 sleeper sofa.
Quaint, quiet, and the quality of a bo.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

LongBoat Key Cottage 10.0

WE ARE RENTING A FANTASTIC KEYWEST STYLE COTTAGE ON THE BEACH OF LONGBOAT KEY FLORIDA JUST STEPS TO THE SANDY BEACH OF THE GOLF OF MEXICO. PERFECT FOR SWIMMING, STROLLING ALONG THE BEACH AND WATCHING THE SUNSET, BUILD SAND CASTLES. IT HAS 3 BEDROOMS, A SOFA BED , 2 BATHS, A LIVING ROOM, DINING ROOM, FULLY EQUIPPED KITCHEN AND A FRONT PORCH WITH RO.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Longboat Key Private vacation home 10.0

Come stay for a month and discover this Hidden Beach/Bay 4 Bedroom Gem and enjoy all the amenities in your home away from home. Feed your outdoor appetite and enjoy the beautiful weather in this magnificently manicured tropical oasis. These spacious grounds are situated on 1.8 acres of land that also features a private, full-size, fenced tennis / P.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 8

Vacation Home

Longboat Key Condo 9.6

FL Vacation Connection offers this 2brm luxury condo. 3rd floor. 1700 sq ft. 52' beachfront balcony. Large living area. Living, dining, and bedrooms open to balcony. Designer kitchen with Thermador appliances, dolomite marble backsplash, waterfall dining table, white quartz countertops, and acacia wood paneling. King in Master, dressing area, .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.8

Offered by FL Vacation Connection, this island getaway is located on the southern tip of Longboat Key with beautiful beach views and pool area. Located on the 10th floor, you will enjoy gorgeous views in this beachfront property. The living and dining area and both bedrooms open to the lanai plus you have a full kitchen. Both full bathrooms offer .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Condo 10.0

WELCOME TO Longboat Key, Florida!

Our beautiful PENTHOUSE UNIT at BEACHPLACE, named “Bird’s Eye View”, has a breathtaking full view of the Gulf of Mexico from the master bedroom, living room, kitchen and dining room. The guest room and kitchen look out over Sarasota Bay. The unit was purchased from an original owner and on the market .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Apartment 10.0

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHFRONT Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.
Updated stunning BEACHFRONT condo, .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.4

We have two units in this condo building. One on the 2nd floor and one on the 7th. Both with magnificent Gulf of Mexico views.

Please DO NOT try to book this property initially as there is an approval process including a background check which can take about a week. Simply "Ask Owner A Question" first, then once approved we can go to the.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.8

This large and airy 2 bedroom condo is right on the beach. It is a corner unit on the ground floor and it is very private and peaceful. No stairs - just step right outside. The ideal spot for a relaxing getaway and memorable sunsets.

This easy access ground floor unit offers two-bedrooms, two-bathrooms, a spacious living room, a full-size k.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Apartment 9.4

Offered by Florida Vacation Connection, enjoy this spacious 650 square feet beachfront Club Suite. This perfect island getaway is located behind the gates on the prestigious southern tip of Longboat. The dressing area is updated with blue Brazilian granite counters resembling the blue Gulf waters and the bathroom with Italian porcelain tile and an.......read more

Studio
1 Bath(s) Sleeps 2

Vacation Home

Longboat Key Private vacation home

PLEASE SEE COVID 19 AND STANDARD POLICIES BELOW - it is different from VRBO policy options as are payment options. Arrivals prior to 90 days are to be paid in full. Please note that the minimum lease period a month. due to City Code restrictions. We are not able to make an exception.Welcome to peaceful Buttonwood Harbour, composed of 50 homes in .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Private vacation home 9.8

Set on 2 acres of land on a 38 acre private island, this award winning home will provide an island vacation experience for you and your family like no other.

The house has 4 bedrooms and 4 bathrooms and an outdoor shower. All rooms view out over the azure waters of Longboat Pass, with 300 feet of beachfront, palm trees, shaded hammocks, an.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 10

Vacation Home

Longboat Key Private vacation home 9.6

Welcome to Longboat Key - paradise awaits! Large newly renovated, spacious and bright 2 bed/2.5 bath 3 story townhome with picturesque sunset views and privacy. Located in the Cedars East Tennis Resort Community, complete with a heated Olympic sized pool. Renters have access to clay tennis courts, pickle ball courts and fitness center. Short walk .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 4

Vacation Home

Longboat Key Condo 9.8

GULF FRONT!
One minute walk to the beach.

Please be Advised before booking that this condo doesn't have an ocean/water view from windows or balcony.

Condo completely renovated with everything new September 2021. All new, kitchen, bathroom, floors, furniture, appliances and many more upgrades.

Our location encompass all .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Longboat Key Private vacation home 9.6

Endless gulf views in newly constructed spectacular home with private infinity pool. This unit features a brand new modern kitchen with duel sinks, a 48 inch range, 2 indoor eating areas and 1 outdoor table. There is a fire table and a grill on the main deck overlooking beautiful views. All bedrooms are ensuite with beautiful tiled showers. It is.......read more

3 Bedroom(s)
4 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 10.0

Steps to the heated pool and gorgeous beach - which runs for over ten miles! Run out barefoot to the beach, enjoy a swim or relax on the beach chairs. Enjoy amazing sunsets from the screened lanai, living room or bedroom. Bike on the 12 miles of bike lanes. Convenient restaurants and shops right across the street. A few minutes walk to Durante park.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Longboat Key Condo 9.0

Enjoy spectacular sunsets from this direct Gulf front, 2 bedroom, 2 bath well appointed property. Located on the 5th floor, this unit features a King bed master suite, and two twin beds in second bedroom, flat screen TV's, wireless internet and washer and dryer. This immaculate unit has everything you will need for a relaxing care-free beach vacati.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Longboat Key Private vacation home 10.0

Welcome to Beach & Boaters Paradise a home in a residential community where you will have immediate access to beautiful Sarasota Bay, the Gulf of Mexico and Longboat Key’s sugar white sand beaches and emerald green waters.

Picture yourself vacationing in this beautifully remodeled home on fabulous Longboat Key - perfectly located on a dee.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 8

Vacation Home

Longboat Key Condo

Enjoy beautiful Bay views from this spacious three bedroom two bathroom one-story (no elevator) villa that comfortably sleeps six. Brand new enclosed lanai with outdoor patio and all new windows. Completely updated exterior and interior with designer furnishing and decor. Gourmet eat-in kitchen with beadboard cabinets and stainless steel appliance.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home