We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Longboat Key Holiday Rentals with Pools

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
274 rentals in Longboat Key.
Sort by:
Tripadvisor Sort
Beautiful Condo in Tropical Setting
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
Oceanfront 3 bedroom Condo on Longboat Key- Available in Summer ONLY
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
Charming Beach House in Longboat Key/ pool/pet/dock
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
6 other travellers have booked this property
~ The Beach on Longboat Key ~ * OCEAN FRONT DLX STUDIO *
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
20 other travellers have booked this property
~ BEACH FRONT APARTMENT ~
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
38 other travellers have booked this property
Holiday Home Directly by Sea - Self Catering
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
Lovely Tropical Staycation
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
4 other travellers have booked this property
BeauTrully a Paridise for You Palm Trees
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
Beach front condo in Longboat Key
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
2016 Renovated, Open Concept Resort Property: Pool, Tennis, Bikes, Beach Access
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Booking now for Spring 2021
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Relax In Paradise! Just Minutes From St. Armand Circle And Sarasota Attractions.
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Fun and Elegance In Longboat Key - Beautiful Townhome, Exceptional Reviews!
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Spectacular Beach View, Heated Pool, Tennis Courts
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Can't Get Closer to the Beach Without Getting Your Feet Wet!
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Direct Gulf front Condo on top floor, corner unit
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Georgeous Condo Directly On The Beautiful Longboat Key!!!!
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Steps from Beach or Bay
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Hideaway Bay Exclusive Home – Platinum Waterfront Property
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Beachfront Family friendly where EVERY room has an ocean/beach view!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
A little piece of Paradise! Exceptional Reviews!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
600 Feet to Beach - Pool/5 Restaurants/Conv.Store all close by
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Wonderful Bay Front Condo! See Manatees Right From Your Doorstep!
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Just refurbished luxurious two bedroom Beachplace condo with brand new kitchen!
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Rare Beach to Bay Condo
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
ZILLI VILLA
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
Short Term Rental Condo
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
Best location on Longboat Key
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
GULF FRONT 2 BR 2 BATHROOM CONDO
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
GORGEOUS gated Multi-level LONGBOAT KEY HOME with DOCK ~ Near beach & private!
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
Beautiful, CLEAN, turnkey 1 Bedroom Gulf coast condo. Ground floor. Beachfront.
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Two Story Condo on the Gulf of Mexico
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Beach Castle #12: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Silver Sands #236: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Beach Castle #21: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Silver Sands #243: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Beach Castle #1: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Beach Castle #16: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Sea Pines Secluded Beach Front Condo on Gulf of Mexico
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Silver Sands #247: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Beachplace 3-102: 2 BR / 2 BA Condo on Longboat Key by RVA, Sleeps 4
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Silver Sands #253: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 5
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Silver Sands #253S: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Beach Castle #4: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Silver Sands #255: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
Silver Sands #258: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
The Beach on Longboat Key #101: 1 BR + Den/2 BA Resort on Longboat Key by RVA
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Homeaway.co.uk logo
Check-in
Check-out
PreviousNext
123456