Longboat Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Longboat Key, Florida on RentalSaver.com!

Longboat Key Rentals

From $577 per night (USD)
VRBO
LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $577 per night (USD)
VRBO
From $836 per night (USD)
Expedia
LaPlaya 206C-Gorgeous vistas of the Gulf from this light and bright end unit with private access to the beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $836 per night (USD)
Expedia
From $502 per night (USD)
VRBO
LaPlaya 101A - Step out to the beach from your screened lanai. Light and bright end unit.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota ...
From $502 per night (USD)
VRBO
From $836 per night (USD)
Expedia
LaPlaya 201C-Breathtaking Gulf panorama from this corner end unit.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $836 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Heart of Bradenton Beach, on the Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Relax on your balcony overlooking the bay, steps across the street to the beach. Walk to beach bars, restaurants and sho ...
From $342 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Short walk to beach or take your boat from the canal / dock in your backyard!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This house offers the best of island living - a boat dock out back and deeded private access to the white sandy beaches ...
From $210 per night (USD)
Expedia
From $441 per night (USD)
VRBO
No hurricane damage inside! Gulf front, first floor, two bedroom. A hidden gem!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Paradise found! Gorgeous. Two bedroom, two full bathrooms. Open concept. Leather couches, luxurious bathrooms. Master ...
From $441 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
What's better than your own private paradise? Come and enjoy this beautiful, recently remodeled, canal front 2 bedroom ...
From $415 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Contemporary Coastal Retreat w Gourmet Kitchen & Stunning Gulf Views by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This exquisite Sea Grape Inn is just steps from the sandy beaches of Longboat Key and features a private infinity pool w ...
From $520 per night (USD)
VRBO
From $399 per night (USD)
VRBO
Your Dream Vacation Awaits at Sea N Blue!OCEANFRONT WITH PANORAMIC GULF VIEWS!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ready to swap the hustle and bustle for sun-soaked shores and gentle ocean breezes? Meet Sea N Blue, your ultimate vacat ...
From $399 per night (USD)
VRBO
From $172 per night (USD)
VRBO
Paradise awaits on LBK 2BR/2BA Updated Condo on the Bay with Water Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Meticulously maintained top (3rd) floor condominium located on Sarasota Bay. Private dock, pool, gym and water access. ...
From $172 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Direct Bayfront LBK Condo, Private Beach, Near St Armands, Boat Slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to charming Buttonwood Bliss located in a beautiful, bayside community on Longboat Key. This two bedroom, two ba ...
From $307 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Upscale Oceanfront Condo – Roomy & Refined: Club Longboat #334 by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. This 3-bedroom/ 2 ...
From $366 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Completely Refurbished - Gorgeous Beachside Condo/Townhome on Longboat Key Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. This 3-bedroom/ 2. ...
From $282 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Long Boat Key Vacation Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
This is a two bedroom, two bathroom open layout condo with an ally kitchen and views of both the gulf and the bay. The c ...
From $240 per night (USD)
VRBO
From $895 per night (USD)
Expedia
Amazing Canal Front 4 Bedrm Home, Heated Pool, Dock Putting Green Close to Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Beautifully updated large home on a deep water canal with room for a boat. Resort-like setting with a heated pool, putti ...
From $895 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
🚩30 day minimum rental per town of longboat key 🚩Quiet beach house tucked away in the historic Longboat Village in wal ...
From $298 per night (USD)
VRBO
$3 BEDROOM PENTHOUSE \CRUISE SHIP\ VIEWS w/DOUBLE BALCONY at Beachplace!$
From $710 per night (USD)
VRBO
3 BEDROOM PENTHOUSE \"CRUISE SHIP\" VIEWS w/DOUBLE BALCONY at Beachplace!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Full Wall-to-Wall renovation and re-imagined 3 Bedroom floor plan 2022! 6TH FLOOR PENTHOUSE "CRUISE SHIP" VIEWS WITH DOU ...
From $710 per night (USD)
VRBO
From $373 per night (USD)
VRBO
Direct beachfront private home by FVC
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Tropical Odyssey, a beachfront 4 bedroom home managed by Florida Vacation Connection provides a screened porch with enou ...
From $373 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Buttonwood Cove 104B by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You can't beat the view from this lovely and spacious 2 bedroom, 2 bath, first floor condo! Your private, enclosed lanai ...
From $240 per night (USD)
Expedia
From $582 per night (USD)
VRBO
The Promenade
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
2400Sq/Ft area, charming with 3 lovelly beds and 3 full baths..Condo full of ameneties, concierge, heated pool, privite ...
From $582 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Play by Day, Unwind by Night - Cedars East #852 Pet-Friendly by 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 $321 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Luxury Gulf Condo – Amenities Galore, Steps to Sand - Portobello #204 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Gulf-Front Bliss at Portobello – Unit #204 Escape to the sun-drenched shores of Longboat Key and make Unit ...
From $352 per night (USD)
VRBO
From $955 per night (USD)
VRBO
Precise Realty presents St. Armands Pool Retreat
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
St. Armand`s Circle, is home to this beautifully decorated 6 bedroom 4.5 bath vacation home. A wonderful 2 story pool ho ...
From $955 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Gulf of Mexico Front Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 BR, 2 Bath, 1684 Sq. Ft., gulf front condo located within the Bayport Beach and Tennis Club on Longboat Key, Florida. ...
From $349 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Flip-Flops Required: Your Beachside Bliss Awaits on Longboat Key!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Ready for sun-soaked days and barefoot evenings? Gulf Tides is your summer escape—where the days are long, the pace is s ...
From $322 per night (USD)
Expedia
From $562 per night (USD)
VRBO
Seas the Day: Gulf-Front Bliss Awaits You!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up to the rhythmic waves of the Gulf and sip your morning coffee on your private beachfront balcony, where salty br ...
From $562 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Gulfside Escape at Sea Twig #103- Relax & Unwind Steps to Sand & Pool by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RVA features an intimate beachfront condominium property on the Gulf of Mexico. The quiet beach can be reached by charmi ...
From $510 per night (USD)
Expedia
From $195 per night (USD)
VRBO
Bikini Top Cottage in the historic village of Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Bikini Top Cottage sweet spot for couples. Tiny Home in a Cozy Island village. The bungalow is on an alley way that ...
From $195 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Cedars East Getaway – Tennis, Sunshine & Gulf Breezes - Unit #507 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cedars 507 has been recently renovated by its new owners, from top to bottom. It has an open, airy floor plan with high ...
From $317 per night (USD)
Expedia
From $658 per night (USD)
VRBO
Precise Realty presents The Waterway Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
1 month stay required during seasonal months and 2 week stay required for out of season months. Charming, waterfront ...
From $658 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Unit #308 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bright and sunny; 3rd floor condo: Partial view to beach from private patio. Condo has Cathedral ceilings for spacious ...
From $399 per night (USD)
Expedia
From $437 per night (USD)
VRBO
Unit #210 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Second floor, poolside. Directly over pool. This unit has had numerous upgrades this year including a complete kitchen ...
From $437 per night (USD)
VRBO
From $282 per night (USD)
Expedia
3brm elevated canal front pool home on North Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Coconut Place: Your Canalfront Paradise! Prepare to be captivated by the stunning Coconut Place, a beautiful ...
From $282 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Beautiful Longboat Key Condo Surrounded by Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Immerse yourself in this beautiful 2 bedroom, 2 bathroom condo just steps away from one of the most beautiful beaches in ...
From $246 per night (USD)
VRBO
From $227 per night (USD)
Expedia
Waterfront condo with Gulf views, pool, tennis, & deeded beach access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Whitney Beach 149 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $227 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Cozy private beach condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enj ...
From $325 per night (USD)
VRBO
From $116 per night (USD)
VRBO
Steps from the Water with Spectacular Bay Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up every morning and have coffee from your front patio, just a few feet away from the Sarasota Bay. Play a round of ...
From $116 per night (USD)
VRBO
From $282 per night (USD)
VRBO
Waterfront Longboat Key Retreat With Dream Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Start your days waking up to waterfront views and end your days watching the sunset on the Gulf of Mexico from your priv ...
From $282 per night (USD)
VRBO
From $366 per night (USD)
Expedia
Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step back in time and settle into a slice of Old Florida at Little Gull Cottage, a 2-bedroom, 2-bath coastal retreat tha ...
From $366 per night (USD)
Expedia
From $315 per night (USD)
VRBO
2BR Cottage Bayside of Property, Full Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Longboat Key is a haven for wildlife lovers, where you might spot tortoises, egrets, wild parrots, and even the island's ...
From $315 per night (USD)
VRBO
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Expedia
2BR Cottage Bay Views Bayside
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This spacious retreat features a king bed in the main bedroom, ideal for recharging after a day of beach adventures. The ...
Click For Pricing
Expedia
From $262 per night (USD)
VRBO
Relax and Recharge in this 1BR Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to this charming bayside cottage, featuring a spacious main bedroom with a king bed and a living room with a fire ...
From $262 per night (USD)
VRBO
From $451 per night (USD)
Expedia
3BR Cottage- Footsteps to the Sand
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Step into the charm of Old Florida with this 3-bedroom, 2-bath coastal cottage just steps from the warm waters of the Gu ...
From $451 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Steps from the beach on Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Charming, one-of-a-kind property in a boutique-like setting with only 11 other units. There is a beautiful, heated pool ...
From $177 per night (USD)
VRBO
From $5499 per night (USD)
Expedia
Boater’s Paradise–Pool & Dock, Walk to Beach Seas the Day: Home in LBK by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Seas the Day, a home by RVA. This waterfront home is in the Country Club Shores and has a gorgeous open floor ...
From $5499 per night (USD)
Expedia
From $951 per night (USD)
VRBO
Steps to the Beach! Private Pool, Pet Friendly!
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Coastal Horizons by Anna Maria Vacations Home in Bradenton Beach, Fl 34217 TPL18-000052 Enjoy luxurious living at Coas ...
From $951 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Waterfront Getaway Island Villa at Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax or work remotely at our Waterfront Island Villa on LBK. Nestled 1 block from the beach & on Sarasota Bay, enjoy wa ...
From $182 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Beachfront Bliss: 2/2 with Stunning Gulf Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Dolphin's Retreat, where you can experience the ultimate beachfront vacation! 🏡 Property Highlights: ✨ Bea ...
From $247 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Sutton Place with Private Beach, Pavilion with Grills/Showers, 2 Pools
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise with this beautifully furnished 2-bedroom, 2-bathroom townhome on Longboat Key, Florida. With a beach ...
From $279 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Gulf Beach front Club Longboat Beach & Tennis Assoc 2BDR 2BA Furn Condo Walk Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RATE/AVAILABILITY NOTE: 30 DAY ASSOCIATION MINIMUM BOOKING average In season rental rates (Dec $175)/night (Jan-Apr) ...
From $213 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Starfish Paradise-Beachfront Oasis w Screened Patio & Stunning Sunsets by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcoming Starfish Paradise to RVA's collection of vacation rentals, where a well-deserved beach vacation is guaranteed. ...
From $379 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Beachplace 8-505 Gulf Front by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront Bliss at Beachplace – Your Longboat Key Retreat Welcome to your dream coastal getaway, professionally manag ...
From $236 per night (USD)
VRBO
From $1123 per night (USD)
Expedia
Rooftop deck with Gulf views - Villa Rayo Del Sol
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
Highlights • Right across the street from the Beach • Private Pool and Hot Tub • Rooftop Deck • Ping Pong Table Villa ...
From $1123 per night (USD)
Expedia
From $458 per night (USD)
VRBO
Stunning 2 Bedroom Condo is located on Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Casual yet elegant living area directly on the gulf and just steps from the beach. Enjoy breathtaking sunsets on the Gul ...
From $458 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Stunning one bedroom Cape Cod style Cottage on Long Boat Key, Florida
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy breathtaking sunrises on Sarasota Bay. This one bedroom, well appointed cottage sleeps four. Unit 11 features one ...
From $299 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Gorgeous Remodeled 2 Bedroom Longboat Key Condo with Stunning Bay Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 2 bedroom/2 bath recently updated condo on Longboat Key looking over stunning Sarasota Bay. Top 3rd floor -wi ...
From $238 per night (USD)
VRBO
Click For Pricing
Expedia
SUNSET VISTA ON LONGBOAT KEY
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gorgeous 1,110 sq.ft., renovated condo on the 3rd floor in Beach Harbor Club. This 2 bedroom/ 2 bath condo has been comp ...
Click For Pricing
Expedia
From $644 per night (USD)
VRBO
Absolute Tranquility by FVC
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Professionally managed by Florida Vacation Connection, Absolute Tranquility is your perfect escape to luxury and peace. ...
From $644 per night (USD)
VRBO
From $246 per night (USD)
VRBO
2 Mi to Bradenton Beach: Water-View Home w/ BBQ
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to paradise when you book a stay at this stunning 3-bedroom, 2-bathroom home in Bradenton! Perfectly situated nea ...
From $246 per night (USD)
VRBO
From $4399 per night (USD)
VRBO
Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block.
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
Let's get straight to the point: THERE IS NO FINER RENTAL HOME on Lido Key! From the exquisite residence to its extensiv ...
From $4399 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Tropical Escape–Private Pool Home Near the Sand Hy Tee on Longboat Key by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Hy Tee, a charming coastal retreat nestled on Longboat Key, Florida. This beautiful vacation home promises a ...
From $293 per night (USD)
Expedia
From $810 per night (USD)
VRBO
Recently updated 5 bedroom home, private pool and steps to the beach.
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
Newly updated home!!!!! Updates include: pool re-finished and new components, interior and exterior of home painted comp ...
From $810 per night (USD)
VRBO
From $530 per night (USD)
Expedia
650 Norton - Longboat Key - Canal Home with private Pool - 3 Bedroom/ 2 Bath,...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
650 Norton - Longboat Key - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. Canal Home - Private Pool - Distance ...
From $530 per night (USD)
Expedia
From $347 per night (USD)
VRBO
Bayfront home with dock, amazing views, outdoor areas, & kayak
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Beach to Bay View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $347 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Beach Castle Resort, 1st Floor, Pool, Walk to Beach/Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to a tranquil paradise on Longboat Key and discover the hidden gem known as Pura Vida, a delightful 2-bedroom, 2- ...
From $429 per night (USD)
Expedia
From $259 per night (USD)
VRBO
Tropical Haven *B
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Premier local manager, Destination Paradise welcomes you to “Tropical Haven B”… a poolside resort experience, without th ...
From $259 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Tropical Haven *A
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Premier local manager, Destination Paradise welcomes you to “Tropical Haven A”… a poolside resort experience, without th ...
From $294 per night (USD)
Expedia
From $510 per night (USD)
VRBO
Unit #101 Sand Cay, Gulf View, Steps to Beach, Recently Remodeled
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This privately located ground floor Gulf View unit was just remodeled with new paint and new luxury vinyl flooring. Well ...
From $510 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Home away from home in LBK
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Relax with the whole family at this peaceful place to stay. The home offers an ample attached single car garage with sto ...
From $177 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Beach Castle Resort, Pool, Private Beach and Bayfront
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled within the enchanting enclave of Longboat Key lies a true hidden gem - a fully updated 1 bedroom, 1 bath 2nd-flo ...
From $390 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Harbour Hideout: Condo on Longboat Key by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy elevated views that span the harbourside greens from the comfort of the 3BD/2BA villa residence positioned behind ...
From $437 per night (USD)
Expedia
From $411 per night (USD)
VRBO
Turtle Shores BEACHFRONT Retreat! Waterfront oasis to completely unwind!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Pool update: we continue to wait for final approval for the permit to be issued allowing guests to freely enjoy the reb ...
From $411 per night (USD)
VRBO
From $250 per night (USD)
VRBO
2 bedroom/2bath private home in Longbeach Village on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your vacation home! The elevated living space includes a master BR with en-suite bathroom and private balcony ...
From $250 per night (USD)
VRBO
From $303 per night (USD)
VRBO
Charming 2/2 ground floor condo located in Beach Harbor Club on Longboat Key - Sea Ya
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sea Ya! Professionally managed by Gulf Coast Vacation Rentals. A condo in the desirable Beach Harbor Club on ...
From $303 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Breathtaking beach views await from this 2/2 2nd floor condo on Longboat Key - The Beach Fact Oar
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Breathtaking Direct Gulf views from this second-floor condo at Longboat Terrace. Perfect for a small family or travel wi ...
From $432 per night (USD)
Expedia
From $380 per night (USD)
VRBO
Gorgeous Gulf views await from this 3/2 condo on Longboat Key - Snow On The Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This unit is located in the Islander Club, one of the best communities on the Gulf of Mexico. Professionally managed by ...
From $380 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Charming 2 BR Longboat Key condo with ocean view - Flirty Flamingo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the highly sought-after Beachplace on Longboat Key and professionally managed by Gulf Coast Vacation Rentals, ...
From $338 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Exquisite 3 BR / 3.5 BA home with pool and spa on Longboat Key - The Captain's Quarters
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Captain's Quarters! Professionally managed by Gulf Coast Vacation Rentals. This newly built Luxury Rental ...
From $567 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Waterfront, Spa/Pool, Private Paradise On Longboat Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
NOTE: BOOKING JANUARY or FEBRUARY? Please book whole months only NOT mid-month to mid-month. This time frame is a monthl ...
From $433 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Condo- steps to the sand
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your beachfront paradise! Escape to the ultimate seaside getaway and create lasting memories at our stunning ...
From $234 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Waves, White Sand & Private Beach at Club Longboat #312 Condo by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your very own slice of paradise on Longboat Key! #312 at Club Longboat Beach and Tennis Resort is a stunning ...
From $315 per night (USD)
Expedia
From $700 per night (USD)
VRBO
Beachfront 4th floor 4/4 Longboat Key Condo With Stunning Gulf Views - Paradise Sur Mer
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Paradis Sur Mer! Professionally managed by Gulf Coast Vacation Rentals, in need of an ocean view? We have you ...
From $700 per night (USD)
VRBO
From $404 per night (USD)
VRBO
Gulf of Mexico Beach Front ....Walk out condo steps from the private beach!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful main floor two plus bedroom condo with stunning views of the Gulf! Never miss a sunset, watch from the condo o ...
From $404 per night (USD)
VRBO
From $216 per night (USD)
VRBO
Magnificent sunlit beach retreat with pool, grill, balcony, W/D - close to water
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Freesia at Seaside Gardens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $216 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Magnificent Oceanfront 2 BR Condo in Longboat Key - The Lookout
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Lookout! Professionally managed by Gulf Coast Vacation Rentals. This charming fourth-floor 2-bedroom, 2-b ...
From $233 per night (USD)
Expedia
From $153 per night (USD)
VRBO
Gorgeous canal front condo, fully equipped and just minutes from the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You'll love the carefree living at this condo. It's fully equipped for your daily needs with updates throughout. Spend y ...
From $153 per night (USD)
VRBO
Click For Pricing
Expedia
OceanVista Beachfront Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you ...
Click For Pricing
Expedia
From $3312 per night (USD)
VRBO
Castle on-the-Bay - St. Armand’s/Lido Beach 6 BD, Pool/Spa, Boat & Jet Ski Dock
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
This St. Armand's bayfront estate home has spectacular panoramic views of Sarasota Bay and the downtown city lights. Th ...
From $3312 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Beach lovers dream
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our 1st floor beachside condominium, just steps from the beach on Longboat Key. The spacious three bedroom, t ...
From $285 per night (USD)
Expedia
From $322 per night (USD)
VRBO
DIRECT Gulf Front view from the 4th floor condo at Tiffany Plaza
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Looking to work remotely during the summer and fall? Why not consider working right on the beach? Direct Gulf Front Ren ...
From $322 per night (USD)
VRBO
From $524 per night (USD)
VRBO
Sea Club Iii Beachside Condo On Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SEA CLUB III - WEEKLY VACATION RENTAL - BEACHSIDE CONDO ON LONGBOAT KEY. Perfect Location on the beaches o ...
From $524 per night (USD)
VRBO
From $135 per night (USD)
VRBO
Bermuda-esque Island Cottage! Steps to Sand! Beach to Bay
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to this cozy, light-filled cottage, completely rebuilt in 2025 with a brand-new kitchen featuring stainless steel ...
From $135 per night (USD)
VRBO
Click For Pricing
Expedia
Spectacular penthouse on white sandy Longboat Key beach with incredible views.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on the barrier island complete with wetlands, biking paths, and plenty of wild birds, Gulf Tides is a fantastic ...
Click For Pricing
Expedia
From $328 per night (USD)
VRBO
Modern Beach Condo–Walk to Gulf, Pool + More Beach Harbor Club B305 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our exquisite beachfront getaway on Longboat Key – a newly updated 2-bedroom, 2-bath condo that promises an i ...
From $328 per night (USD)
VRBO
From $1102 per night (USD)
Expedia
Waterfront w/Putting Green, Heated Pool, Dock -Manatee Cove
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Manatee Cove by Lido Key Vacations Home in Sarasota, FL 34236 VR24-00003 Minimum stay duration of 7 days/nights Welcom ...
From $1102 per night (USD)
Expedia
From $1757 per night (USD)
VRBO
Waterfront home with private beach, a private pool, and water activities! Moku
Bedrooms:
5
Bathrooms:
5
Sleeps:
15
Moku by AMI Locals 7147 La Lenaire Dr Longboat Key, Florida BTR#12879.2025 and RRR-00784.2023 Welcome to Moku, a water ...
From $1757 per night (USD)
VRBO
From $221 per night (USD)
Expedia
Beachplace 11-305 (3BR) by FGC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom and 2 Bath condo located in the resort community of Beachplace Association. Faces the golf course and has ac ...
From $221 per night (USD)
Expedia
From $494 per night (USD)
VRBO
Longboat Key Townhouse in Cedars East, Longboat Key Florida
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Enjoy the beach life on Longboat Key! This property is ready for you to enjoy Longboat Key beaches. Kick back and relax ...
From $494 per night (USD)
VRBO
From $520 per night (USD)
Expedia
Your warm, winter, paradise in luxurious Longboat Key Florida!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
One week Penthouse on beach of Longboat sleeps up to 10! Jan 18th to the 25th availibility! Veranda Longboat Key Beach R ...
From $520 per night (USD)
Expedia

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Results: 679 Rentals