
Longboat Key Rentals
- From $295 per night (USD)
VRBO
Cozy Cedars East Townhome #622 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $295 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Silver Sands 1BR – Gulfside Comfort #255 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $385 per night (USD)Expedia
- From $375 per night (USD)
VRBO
2nd Floor Retreat – Silver Sands #251 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $375 per night (USD)VRBO
- From $316 per night (USD)
Expedia
Cedars East Bayview Tennis & Pool Unit 822 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the ultimate Longboat Key getaway at Cedars Tennis Resort, where luxury living meets the beauty of Florida’s Gu ...
From $316 per night (USD)Expedia
- From $430 per night (USD)
VRBO
Charming Beach Condo – Silver Sands Resort #240 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $430 per night (USD)VRBO
- From $394 per night (USD)
Expedia
Relax & Play – Cedars East 2BR #850 RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $394 per night (USD)Expedia
- From $251 per night (USD)
VRBO
Gulf Coast Getaway–Cedars East Tennis #509/RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $251 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Beachfront Longboat Key Outrigger #7 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger ...
From $399 per night (USD)Expedia
- From $558 per night (USD)
VRBO
Silver Sands #245S Resort by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $558 per night (USD)VRBO
- From $329 per night (USD)
Expedia
Cozy Beach Studio – Silver Sands #251A by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $329 per night (USD)Expedia
- From $329 per night (USD)
VRBO
Beach & Tennis Paradise–Cedars East #806 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $329 per night (USD)VRBO
- From $430 per night (USD)
Expedia
Elegance Meets Ocean – Silver Sands #248 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $430 per night (USD)Expedia
- From $329 per night (USD)
VRBO
Courtside Getaway – Cedars East #605 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $329 per night (USD)VRBO
- From $627 per night (USD)
Expedia
Direct Beach Access – Silver Sands #249 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $627 per night (USD)Expedia
- From $383 per night (USD)
VRBO
2nd-Floor Gulffront Outrigger #6 Condo by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger ...
From $383 per night (USD)VRBO
- Click For Pricing
Expedia
Beach Bungalow: Best Canal, Dock, Beach, Pool, Pet Friendly. Renovated in 2025
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful and spacious 3 bedroom house underwent a total renovation in 2025, it's brand new. Located on one of the ...
Click For PricingExpedia
- From $221 per night (USD)
VRBO
1st Floor 2 Bed 1 bath home, short walk to beach, 1 step to door, North end LBK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private Beach Cottage ground floor apartment. This ground floor apartment has two bedrooms, one bath, Living Room and ...
From $221 per night (USD)VRBO
- From $588 per night (USD)
Expedia
Unit #318 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind and make memories in this sun-filled unit with stunning Gulf-front and beach views. Accommodation for up to 6 wit ...
From $588 per night (USD)Expedia
- From $368 per night (USD)
VRBO
Coastal Elegance 3BR w Private Balcony, Pool & Direct Gulf Access by RVA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
RVA welcomes you to Villas of Avignon - where you can enjoy a secluded beach, heated community pool, private balconies a ...
From $368 per night (USD)VRBO
- From $241 per night (USD)
Expedia
Bayside 2BR on Whitney Beach w Canal Views, Pool, and Private Lanai by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on a superb pristine beach with ne ...
From $241 per night (USD)Expedia
- From $507 per night (USD)
VRBO
Sunset and beach view from your balcony Unit 403
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
A luxurious beachfront experience awaits you on the beautiful white sands and emerald waters of the Gulf of Mexico when ...
From $507 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Beachside at Whitney Beach: 2BR Ground-Floor Condo w Gulf Views & Pool by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on a superb pristine beach with ne ...
From $249 per night (USD)Expedia
- From $426 per night (USD)
VRBO
Island Time: Open Sept 13th - 16th!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in e ...
From $426 per night (USD)VRBO
- From $424 per night (USD)
Expedia
DOG FRIENDLY and PERFECT LBK LOCATION
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Calendar not always updated. Messege me for specific dates. Newly ren ...
From $424 per night (USD)Expedia
- From $939 per night (USD)
VRBO
3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Priority for inquiries bundling Jan AND Feb TOGETHER. No half months please. February alone is not available. FULL WA ...
From $939 per night (USD)VRBO
- From $320 per night (USD)
Expedia
Beachcomber unit 403
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...
From $320 per night (USD)Expedia
- From $321 per night (USD)
VRBO
Beachcomber unit 405
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...
From $321 per night (USD)VRBO
- From $320 per night (USD)
Expedia
Beachcomber unit 203
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly Refreshed Beach Condo - Unit 203 Welcome to our beautifully redesigned and refreshed condo. In Novemb ...
From $320 per night (USD)Expedia
- From $323 per night (USD)
VRBO
Beachcomber unit 303
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our building is located on the beach, this unit has an ISLAND view. Enjoy upscale Longboat Key in the elega ...
From $323 per night (USD)VRBO
- From $496 per night (USD)
Expedia
Beachcomber unit 204
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a great location directly on the beach with a spectacular view of the Gulf of Mexico. This Gulf fro ...
From $496 per night (USD)Expedia
- From $323 per night (USD)
VRBO
Beachcomber unit 305
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our building is located on the beach, this unit has an ISLAND view. Pack your bags, invite your family and ...
From $323 per night (USD)VRBO
- From $702 per night (USD)
VRBO
Longboat Key Luxury Condo - walking to St. Armand's Circle!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This luxurious COVID free top floor end unit condo was newly furnished in 2022 and features an elevator. Taking in v ...
From $702 per night (USD)VRBO
- From $815 per night (USD)
VRBO
Canal Front Home - 8 min walk to beach. RRR-00953.2023
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Completely remodeled in 2022 this canal front with pool home is located on the beautiful Island of Longboat Key. Pull y ...
From $815 per night (USD)VRBO
- From $257 per night (USD)
VRBO
Longboat Key Beachfront Incredible 2/2 Postcard Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy beachfront living, captivating ocean views, spectacular sunsets and balcony access from every room. Wake up each m ...
From $257 per night (USD)VRBO
- From $396 per night (USD)
VRBO
7th Heaven by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to 7th Heaven on beautiful Longboat Key! A beachfront escape directly on the Gulf of Mexico with views of turquo ...
From $396 per night (USD)VRBO
- From $273 per night (USD)
VRBO
Country Club Long Boat Key Beach Villa 2B 3BA Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Longboat Key Rental Registry Number: RRR-01566.2026 Villa is 15 steps from your own private sugar sand bay beach. Ced ...
From $273 per night (USD)VRBO
- From $496 per night (USD)
VRBO
Beachcomber unit 202
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Staying on Longboat Key means you get to experience what Heaven on Earth feels like. A place where you can walk on prist ...
From $496 per night (USD)VRBO
- From $320 per night (USD)
Expedia
Beachcomber unit 501
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our building is located on the beach, this unit has an ISLAND view. Relax and Enjoy the Beach, Pool & Longb ...
From $320 per night (USD)Expedia
- From $320 per night (USD)
VRBO
Beachcomber unit 201
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our building is located on the beach, this unit has an ISLAND view. Welcome Snow Birds and Florida locals l ...
From $320 per night (USD)VRBO
- From $491 per night (USD)
Expedia
Unit #114 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our resort has a relaxed, upscale feel. It is great for vacationers seeking peace and tranquility as well as families wa ...
From $491 per night (USD)Expedia
- From $545 per night (USD)
VRBO
Unit #203 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Second Floor, non-smoking unit. Best views to the beach/Gulf in the Sand Cay complex. Three large bay windows looki ...
From $545 per night (USD)VRBO
- From $588 per night (USD)
Expedia
Unit #204 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Second floor non-smoking unit. Accommodates 6 people. Living room has a 110" window with a direct view of the beach/Gu ...
From $588 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Unit #111 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come experience the ultimate white sandy private beach front boutique Florida paradise. When planning a trip to the beau ...
From $495 per night (USD)VRBO
- From $534 per night (USD)
Expedia
Unit #106 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bright, beachy ground floor unit with a lovely view and easy access of the Gulf. Large, extended bedrooms that comforta ...
From $534 per night (USD)Expedia
- From $534 per night (USD)
VRBO
Unit #201 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Quaint, quiet, and the quality of a boutique resort, not the hassle, noise, the impersonal nature of a hotel. You will b ...
From $534 per night (USD)VRBO
- From $495 per night (USD)
Expedia
Unit #209 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just a short walk to the beach, and steps away from the office, fenced in pool, tennis court and laundry facilities. Th ...
From $495 per night (USD)Expedia
- From $588 per night (USD)
VRBO
Unit #303 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to paradise! Now is a great time to escape to the beach where you can destress in an environment that makes it e ...
From $588 per night (USD)VRBO
- From $492 per night (USD)
Expedia
Unit #120 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Front Condo That Has It All Wonderful ground floor unit – walk right to the beach – no steps to deal with! Very p ...
From $492 per night (USD)Expedia
- From $588 per night (USD)
VRBO
Unit #320 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Master bedroom has king size bed and full bath. Second bedroom has twin beds with full bath. Extremely well equipped k ...
From $588 per night (USD)VRBO
- From $494 per night (USD)
Expedia
Unit #105 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...
From $494 per night (USD)Expedia
- From $534 per night (USD)
VRBO
Unit #205 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience spectacular views from this beautifully appointed and well-located Gulf View (Close to Gulf Front) unit! Now ...
From $534 per night (USD)VRBO
- From $551 per night (USD)
Expedia
Unit #104 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...
From $551 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Unit #107 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...
From $495 per night (USD)VRBO
- From $551 per night (USD)
Expedia
Unit #116 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
First floor Gulf front. King bed in the master, Two full beds in guest bedroom. The bedrooms are extended adding extra s ...
From $551 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Unit #311 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Third floor unit looks over the heated pool of Sand Cay. Decorated unit has all the luxuries of home. Quaint, quiet, an ...
From $495 per night (USD)VRBO
- From $545 per night (USD)
Expedia
Unit #219 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
All new appliances, granite and walk-in master shower. Living space has a Hi def flat-screen TV. Comfortable and cozy, ...
From $545 per night (USD)Expedia
- From $588 per night (USD)
VRBO
Unit #217 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Second floor, The kitchen/living room was renovated / furnished in 2017. All new bathrooms and bedrooms renovated in 20 ...
From $588 per night (USD)VRBO
- From $551 per night (USD)
Expedia
Unit #117 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beachfront, Beachfront, Beachfront! You cannot get any closer to the beach! Just walk out your patio and your toes are i ...
From $551 per night (USD)Expedia
- From $492 per night (USD)
VRBO
Unit #306 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Third floor,. Living room and master bedroom has new furniture. Murphy bed in living room. Quaint, quiet, and the qualit ...
From $492 per night (USD)VRBO
- From $534 per night (USD)
Expedia
Unit #315 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
#315 is a beautiful, light, bright, spacious 2 Bedroom 2 Bath 3rd Floor Condominium with gorgeous views of the Gulf of M ...
From $534 per night (USD)Expedia
- From $492 per night (USD)
VRBO
Unit #301 Sand Cay Beach Resort Gulf View 7 Night Minimum
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our totally renovated home. Located on the top floor of building 4 next to 11 lovely quiet condominiums. You ...
From $492 per night (USD)VRBO
- From $453 per night (USD)
Expedia
Unit #307 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bright and sunny two-bedroom two-bathroom condo in a small resort located on the beach. Top floor unit with elevator acc ...
From $453 per night (USD)Expedia
- From $551 per night (USD)
VRBO
Unit #216 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Breathtaking Gulf front views awaits, salt life could not be better! Enjoy spectacular sunset views, steps from the beac ...
From $551 per night (USD)VRBO
- From $492 per night (USD)
Expedia
Unit #215 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stunning Gulf-Front Condo-Fully Renovated-Sleeps 6-Sunset Views Enjoy breathtaking sunsets from this beautifully renova ...
From $492 per night (USD)Expedia
- From $588 per night (USD)
VRBO
Unit #118 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...
From $588 per night (USD)VRBO
- From $490 per night (USD)
Expedia
Unit #109 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...
From $490 per night (USD)Expedia
- From $453 per night (USD)
VRBO
Unit #108 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This sought after, BEAUTIFULLY FURNISHED, two bedrooms, two bath FIRST FLOOR END UNIT offers fully renovated kitchen an ...
From $453 per night (USD)VRBO
- From $588 per night (USD)
Expedia
Unit #316 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unit can accommodate up to six people with the sleeper sofa in living room. This unit is a must rent for a first class ...
From $588 per night (USD)Expedia
- From $490 per night (USD)
VRBO
Unit #113 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Extended bedrooms. Amenities include 3 televisions with DVD and washer and dryer. Quaint, quiet, and the quality of a bo ...
From $490 per night (USD)VRBO
- From $495 per night (USD)
Expedia
Unit #314 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Light and bright, close to the elevator, this third floor condo is garden view, midway between the pool and beach. The ...
From $495 per night (USD)Expedia
- From $588 per night (USD)
VRBO
Unit #103 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unit 103 is completely renovated, stylish and modern in hues of grey, black and white, complemented by all new furnishin ...
From $588 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Unit #110 Sand Cay Beach Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfect for families! First floor by the pool with "Private Front Yard" landscaping. View of the Gulf of Mexico from li ...
From $450 per night (USD)Expedia
- From $971 per night (USD)
VRBO
Unit #304 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Great family unit features spectacular views of the Gulf of Mexico & and the property's lovely garden. Quaint, quiet, a ...
From $971 per night (USD)VRBO
- From $481 per night (USD)
Expedia
Unit #115 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
All new floors, bathrooms, kitchen, furniture, mattresses, appliances and more. Brand new open layout., including a firs ...
From $481 per night (USD)Expedia
- From $588 per night (USD)
VRBO
Unit #102 Sand Cay Beach Resort Gulf Front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
First floor Gulf Front. Extended bedrooms. Recently redecorated. Private and very near Gulf. The kitchen is elegant ...
From $588 per night (USD)VRBO
- From $490 per night (USD)
Expedia
Unit #312 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Third floor,, with balcony and View of Gulf, unit. Must see! Open living room with vaulted ceilings. Light and brightl ...
From $490 per night (USD)Expedia
- From $492 per night (USD)
VRBO
Unit #305 Sand Cay Beach Resort Gulf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Light and elegant, third floor with high ceiling and Bay windows, non-smoking unit. Open kitchen, newly renovated baths, ...
From $492 per night (USD)VRBO
- From $533 per night (USD)
Expedia
Unit #317 Sand Cay Beach Resort Gulf Front 7 night minimum
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
No walls interrupt panoramic gulf views in this beautifully renovated condo. With soaring ceilings and tiled floors, th ...
From $533 per night (USD)Expedia
- From $671 per night (USD)
VRBO
Direct Beachfront Gulf with Amazing Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
LongBoat Key wins Conde Nast Traveler Award _______________________________________ **Our unit has its own Full sized ...
From $671 per night (USD)VRBO
- From $543 per night (USD)
Expedia
Stunning -late summer sale 50 ft from sand, Private Island 125 +review
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full ki ...
From $543 per night (USD)Expedia
- From $812 per night (USD)
VRBO
1 of a kind home 13 steps to sand LATE SUMMER SALE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to the Zilli family Villa beach house on Longboat Key. After using this 2,000 sf home for their own family vacat ...
From $812 per night (USD)VRBO
- From $478 per night (USD)
Expedia
3/2 Direct Beachfront Condo, Pool, Fitness, Tennis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beachplace Condo: A 3-Bedroom Modern Oasis on Longboat Key by FVC Step into the epitome of modern beachfront living wit ...
From $478 per night (USD)Expedia
- From $218 per night (USD)
VRBO
Longboat Key Cedars Beach House-Pet Friendly-2 Minute Walk To The Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most ...
From $218 per night (USD)VRBO
- From $412 per night (USD)
VRBO
Longboat Key Beachfront - Beautifully Updated with Prime Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come enjoy this beautiful beachfront condo! Completely renovated and updated,, this condo is located at the desirable ...
From $412 per night (USD)VRBO
- From $593 per night (USD)
VRBO
End-of-summer sale ready for a luxury 5-floor penthouse 60 ft from water,
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the ...
From $593 per night (USD)VRBO
- From $601 per night (USD)
Expedia
Beachfront Villa on Serene Gulf of Mexico
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
LongBoat Key wins Conde Nast Traveler Award _______________________________________ **Unit has its own Full sized was ...
From $601 per night (USD)Expedia
- From $213 per night (USD)
VRBO
Canal front home on Longboat Key -Just Steps to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Newly renovated and spacious canal-front home in beautiful Longboat Key with deeded beach access just steps down the str ...
From $213 per night (USD)VRBO
- From $302 per night (USD)
Expedia
Peaceful Condo – Cedars East #803 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $302 per night (USD)Expedia
- From $375 per night (USD)
VRBO
1BR Beach Getaway – Silver Sands #254 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $375 per night (USD)VRBO
- From $420 per night (USD)
Expedia
Gulf Views – Silver Sands #250, Longboat Key by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $420 per night (USD)Expedia
- From $216 per night (USD)
VRBO
Cozy condo in Cedars East
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cozy Condo in Cedars East is a place for you to unwind and revive yourself. Only a 5 minute walk to the beach. Close to ...
From $216 per night (USD)VRBO
- Click For Pricing
Expedia
1st Floor Beachfront Luxury–Ocean Views Included Club Longboat #516 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA invites you to experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. ...
Click For PricingExpedia
- From $497 per night (USD)
VRBO
Beachcomber unit 504
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Beachcomber is a jewel on the luxurious island of Longboat Key, located directly on the white sandy beach of the Gul ...
From $497 per night (USD)VRBO
- From $423 per night (USD)
Expedia
Dolphin’s Den: Seaside Escape w Rooftop Gulf Views & Private Beach by RVA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience this peaceful beach vibe at the Dolphin's Den in Longboat Key located in a clean, quiet private cul-de-sac. J ...
From $423 per night (USD)Expedia
- From $332 per night (USD)
VRBO
Beautiful private beach and backyard pool at our restored Old Florida house!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Beach cottage on a double lot with fenced yard on Long Boat Key Barrier Island. This 3 bedroom two full bath 50s ranch w ...
From $332 per night (USD)VRBO
- From $517 per night (USD)
Expedia
BOOK NOW - BEAUTIFUL HOME NEAR BEACHES
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighborhood. Enjoy the nearby p ...
From $517 per night (USD)Expedia
- From $416 per night (USD)
VRBO
Gorgeous Gulf views and a beachfront location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
From the moment you walk in the door of this 2 1/2 bedroom, 2 bath beach front condo you will know you made the right ch ...
From $416 per night (USD)VRBO
- From $207 per night (USD)
Expedia
Perfect cottage! Million dollar views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Adorable beach cottage with million dollar views of Sarasota Bay out front and a canal out back. Gorgeous seating in bot ...
From $207 per night (USD)Expedia
- From $254 per night (USD)
VRBO
2/2 Beachplace Condo, Beach, Pool, Fitness, Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Proudly offered by FL Vacation Connection, this property is ideal for professionals working remotely! Beautifully furn ...
From $254 per night (USD)VRBO
- From $195 per night (USD)
Expedia
2/2 Condo LBK, Pool, Fitness, Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Offered by FL Vacation Connection, this fifth floor condo has views of the reflecting pond and fountain as well as a par ...
From $195 per night (USD)Expedia




































































































